I was lost in thought while working out today as I was recalling the details of an experience I had with a redditor few days ago. I aroused myself and had to finish my workout quickly to touch myself in the shower as thoughts of my encounter with him left me with intense feelings of desire and lust.
It was not my first time with him. Our first encounter was around a week ago after he responded to my dirty r4r for voice chat, propositioning we meet instead. Though I didn’t feel like meeting him at first, I ultimately gave in to his devilish messages. He was persistent and I was totally driven by uncontrollable urges— . After few weeks of traveling abroad and having no sexual contact, I was ready to be wild with someone random and satisfy my sexual appetite.
We had agreed to meet at the bar but the hot and steamy messages got me so aroused that I just invited him straight to my place. I couldn’t wait. We touched, kissed, fucked. He was rough, and I liked it. My memory of how it felt gets my heartbeat racing every time. Just his finger inside my pussy got me squirming and squealing and gave me a mind blowing sensation that kept me wanting more. He fucked me hard and I was completely subdued when he came all over me. He promised another playful fuck-date before the holidays, this is the story of our second encounter:
We had texted in the weekend but he wasn’t available to meet. Monday morning, however, while at work, he sent a text: “I want a taste of your juicy cunt”—Not romantic, I know, but exactly what I wanted to hear. I was hooked, again.
He followed his message with further persistence “I want my face between your thighs right now”— He then sent a pic of his cock, rock-hard ready to fuck! By now my mouth was watering trying to figure out ways where I could get my lips around his cock. I was ready to play by whatever rules he wanted. We agreed that he would come over when I was done with work and so we met at my place again late afternoon/early evening.
It was not exactly happy-hour time, but I had a shot before he arrived to get me in the mood, (the more for me the sluttier I get). I was slightly nervous, it was our second time and I was scared that he would be rougher than the last time. He was respectful all the way, but he also has a way of making me push my boundaries a bit, and he gets me curious. How dirty can this entire thing get? How far can I go? I have been shy the entire fucking majority of my life and I had enough of being the little coy girl. I wanted to explore not just the things he could do to me, but the things that I am capable of too.
As soon as he came in, he undressed and we laid down in bed for a bit watching porn. It felt nice. He was taking it slow this time and tried to put me at ease…We watched a little bit of anal, cumswapping, FMF action and squirting (I was hoping that he would train me to squirt). He liked cougar stuff, and although we are both in our thirties, I was wondering if the fact that I am 3 years older than him could have turned him on. He also introduced me to gonewild on reddit. We browsed pictures of girls and talked about which one we would love to fuck… It was all very titillating. As I was flipping pictures he would twist my nipple and squeeze them hard. I felt my juices between my legs and on my fingers as I touched myself…. my pussy opening up and getting wetter each second, I grabbed his hand and guided it to my wetness. I wanted him to feel how ready I was for him.
He stroked my clit, little gentle pulses that put me close to orgasm, and then he fingered my pussy so hard, long deep strokes inside me. His thrusting back and forth with his finger just got me so fucking wet and left me craving for his cock inside me. He pulled his finger from my pussy into my mouth. “I want you to taste yourself ” He said, putting one finger, then two…I sucked off his finger as I closed my eyes and pictured myself getting a cum shower. I knew I wanted him to fuck me…I was so aroused, and there was no time for foreplay.
I buried my face between his legs, licking everywhere from his cock to his ass, kissing every inch of it. I moaned as I bobbed my head up and down his hard cock. With each stroke my tits swayed and his hands would reach occasionally twisting my nipples and slapping them. I had not had that done to me before and I felt my nipples harden with his every touch, gentle or rough. I continued to lick up and down, nibbling, sucking, kissing, then nibbling and sucking and kissing again before taking his cock deep in my mouth. I looked at him as he was laid back enjoying every second of it. I knew he enjoyed me going lower on him, that’s when he really started talking dirty to me…. I licked my finger and gave him little pulses on his ass “Oh Yes!” He moaned, and then he commanded: “Suck my balls you dirty little cum slut”. “Will you cum for me?” I asked. “Not yet, not before I fuck you first” He said. I grinned and did as he asked.
We swapped positions so we would enjoy each other simultaneously, he stood up with my mouth facing his groin while I laid my head on the edge of the bed…. He leaned over and parted my legs, putting his face between my thighs…. I felt his tongue on my clit and I nearly died… long deep strokes that left me gasping for air, his fingers penetrated my pussy while he was sucking my clit, I was trembling and moaning so loud that’s when he said: “If you are going to moan like this do it while sucking.”
My head was back all the way on the edge of the bed and my mouth was wide open for him, inviting his cock to my throat… He started thrusting his cock into my mouth, gently at first and then harder while squeezing my nipples, dipping his cock in and then out, going deeper each time. It was torture….He was eating my pussy while training my throat. It was too much pleasure all at once.
He then turned me around and said: ”I want to fuck your tits and cum on them, and cum on your face” “Is that before or after you fuck me?” I responded, hoping he would cum twice, and before he answered, he flipped me on my back and smacked my ass so hard, repeatedly, then he spread my butt cheeks and fucked me with his finger. He flipped me again on my back, reached out for the condom and then rubbed my pussy with a bit of lube and thrusted his cock in. He thrusted deep and hard while pressing gently at my neck…I was gasping for air…he slapped my breasts again and pulled my nipples while fucking me hard I felt like I was going to split in two.
For the next hour, he fucked me in every possible way imaginable and left me no room to breathe…. He bent me over, grabbed my ass and pounded me from behind, his balls slapping against me…He fucked me doggy style while spanking my ass so hard. I was squeezing my nipples and stroking my clit to assuage from the pain I felt. “You are loud” He said, but the louder I moaned the harder he fucked. There was no mercy.
He then flipped me over laid on this back and asked me to be on top, so I straddled his thighs while sitting on his cock, I could feel his big long cock tearing up my pussy, he reached for my breasts and squeezed them. Slapping my breasts again while they swayed. There wasn’t a second of this that I wasn’t enjoying. Then he laid me on my back, spread my legs wide open, thrusted his cock deep in and fucked me while placing my legs on his shoulder. I was trembling as he was thrusting his cock inside me. It seems like now he was ready to cum…. “Open your mouth, I want to fuck your face now”, and he removed his condom. I bent over on my knees and started to suck him off, and then he said: “Let me hear you say you are my little dirty cum slut” and I obliged. “I am your dirty cum slut and I want your cum in my mouth.” When he was ready, he asked me to lay back as he showered my face and my tits with his cum. He orgasmed, a lot, on my tummy, nipples, face and hair. I was drenched, and awkwardly I felt like I wanted more….
I laid my head on him for a bit as we tried to take pics of his load over my tits but the lighting was a bit off. He got dressed and quickly left to do his Christmas shopping while I stayed in bed for the next 24 hours, totally used up and drained from the experience. I could barely walk the following day. As I am writing this, my pussy is still recovering from all the pounding he did to me and my nipples are so sore….
The entire thing was wild and slutty. It helped me explore the bounds of my sexual comfort. Giving up control in the bedroom has now become my new favorite thing.
It was undoubtedly a nice fucking holiday treat.

He looked young. Very young – Younger than she had ever encountered in two years of searching. His face was childlike in a way she instantly craved, with small dimples on his cheeks and oversized teeth that would present themselves proudly with a wide smile. She took in a short breath at the site of him seated across the restaurant, trying to contain the urge she instantly felt, the flutter that crept through her stomach and into her chest, which seemed to bulge out at the very site of him. He had not seen her enter, and she took the final moment of privacy to take another deep breath and calm herself before approaching. She knew before they went any further, she would have to see identification. He almost looked too young.

He watched her approaching from across the room in a tight black skirt and white blouse that extenuated her features in a way that made him immediately feel as though she was out of his league. She was older, though maintained remarkable beauty for her age. She walked with a confidence that still made heads turn, even as she was pushing 50 years old.

“Jamie?”

She nearly startled the young man, despite approaching the table cautiously to match him with the picture she had memorized from their emails.

“Yes,” he confirmed nervously.

“I’m Karen.”

She extended her hand, and he quickly rose to his feet to accept the gesture, though he kept his eyes glued to the floor.

“Honey,” she titled her head lower to catch his eye sight, “look up at me, okay?”

He immediately followed instructions, snapping his up head and maintaining an anxious gaze.

“Yeah, sorry,” he said.

“It’s okay. I’m Karen.”

“I’m Jamie.”

They shook hands and took their seats in opposite sides of the booth. She remained calm and collected, placing her purse to her side and catching the waiter’s eye as he approached the table.

“Hi folks, how are you tonigh-”

“I think we just want drinks and some privacy this evening,” she said, cutting the waiter off.

“Okay, yes ma’am. What can I get you?”

“Gin and tonic.”

She locked eyes with Jamie and waited for his order. He privately felt as though he was being studied by his drink order, and he was.

“Sprite?” he ordered in the form of a question.

“You got it,” said the waiter, quickly abandoning the table in an attempt to save his tip. Karen smiled over at Jamie, feeling another flutter at the notion that he ordered a child’s, though still trying to mask her desires.

“Please don’t be offended, but before we go any further, I need to see your ID again.”

“I emailed it,” he said, protesting lightly but not wanting to make a fuss.

“I understand, but I’ve been faked out before, and you look very young. Do you mind if I see it again?”

Jamie obliged, reaching into his pocket and pulling out his wallet. He removed his driver’s license and slid it along the table toward Karen. She accepted the card, bringing it off the table just as the waiter returned with the drinks so as not to arouse any suspicious.

“Here you go. Just let me know when you’re ready for the check.”

She waited until he was a safe distance away before glancing at the driver’s license. It was legitimate, his goofy grin only bringing more attention to how young he looked.

“Twenty-three years old?”

“Yeah.”

“Are you aware of how young you look?”

“Yeah, people tell me that a lot.”

“Not a day over sixteen I would guess.”

Jamie quietly nodded his head in approval, unsure of how to respond to the line of questioning. Karen slid the driver’s license back to him, and he quickly moved it back into his wallet while she patiently stirred her drink and grinned across the table.

“I need you to understand, this is not about sex,” she said.

“Um, okay.”

“This about an agreement; a mutually agreed upon roleplay that each of us will partake in willingly. If you don’t want to be a part of that, or if you’re just in this to indulge some MILF fantasy, then it won’t work.”

“Okay,” he continued to nod in approval, sipping his Sprite from a straw, remaining just as nervous.

“Are you attracted to me?”

He gulped his drink, fearing any answer could be the wrong one.

“Um…”

“I’m not playing games Jamie. I don’t want you searching for the right answer when I ask you a question. Are you attracted to me? Answer.”

“Yes,” he quickly blurted out.

“Good, that’s okay,” she reassured him. “You have to be for this to work. You told me you like older women. Do I look like the type of woman you were referring to?” She leaned back and extended her arms slightly, revealing her whole outfit and the cleavage-baring blouse she had saved just for the occasion.

“Yes,” he said, his own heartbeat beginning to race.

“Good. Now why did you pick me?”

“I, um, I’m sor-”

“There are plenty of pretty girls on the internet. Why did you respond to my ad?”

Jamie took in a long sigh and prepared to come clean.

“I…”

“What did I say about hesitatin-“

“I need a place to live, and I don’t have any money.”

“Oh,” the admission took Karen aback, as this was the first she had encountered such a situation.

“Where do you live now?”

“An apartment with a friend and his girlfriend, but they’re kicking me out.”

“I’m sorry to hear that.”

Karen let an awkward moment pass by sipping on her drink. For the first time in the conversation, Jamie filled the silence.

“I’ll do what you want, I want to. But I also need a place to live, and you said I would get a room and free rent.”

Jamie looked around the mostly empty restaurant, occasionally scanning the room to ensure no one he knew was there.

“Why are you so nervous?”

“I’ve just, never met someone like this before, off the internet.”

“Were you afraid I was fake?”

“A little.”

Karen smiled at the boy and quietly admired his fear of the uncertainty. He appeared so unprepared for the world, like someone who needed more nurturement than they had received. She was prepared to take care of him.

“Jamie,” her voiced cut through the air in an authoritative tone, “Please look at me when I’m talking to you.”

Jamie held his head up, now embarrassed by the situation and the position he had placed himself in, and certain that she was about to dismiss him.

“Do you have family who will wonder where you are or want to see where you live?”

“No, not here. My parents live in Chicago.”

She tensed at the thought of his parents.

“Don’t say another word about your parents from now on, understand?

He nodded in approval.

“Please say you understand.”

“I understand.”

“It’s nothing against them, but for this to work I can’t have them in my thoughts. We have to be completely immersed in our roles, and that can’t include them. You can’t talk about your family.”

“Ok, I understand.”

Karen leaned in closer, just enough for Jamie to take a peak down her blouse as she glanced around the restaurant. She pulled her head back and caught his wandering eye. With a subtle motion, she placed her hand on his chin and lifted his eyes back to her.

“Not yet little boy,” she whispered seductively, cause his face to turn red and instigating movement on his thigh.

“Do you remember the list I provided you?”

“Yes.”

“And you are okay with everything on that list?”

“Yes, I think so.”

“You can’t hesitate Jamie. There are things on that list that can actually cause you certain physical pains. Do you need to see the list ag-“

“No,” he corrected himself, “No, I’m comfortable with the list.”

She stared at him, trying to feel out how genuine the statement was.

“You need to understand that this is an agreement based entirely on an honor code. I’m not making you sign a contract or a lease. It has to feel as real as possible for it to work.”

He cracked a small smile, realizing for the first time he might have been chosen, though her whisper turned stern.

“I also need you to understand that our arrangement is between you and me, and you and me only. If I read about it on the internet, you will be out on the street in a minute, got it?”

“Yes.”

She leaned back against the booth, taking another quick sip of her drink and crossing her legs, each one gently passing across Jamie’s feet.

“I’ll send my address in an email tomorrow, and you’ll bring your things over.”

“Okay,” he said, trying to mask the mixed emotions of nervousness and excitement.

“I’ll pay for the drinks. You go now.”

Jamie rose from the table and started his stride toward the door, only to be halted by a firm hand on his forearm. It was the first time they had touched, and Jamie let out a small gasp at the kinetic energy dancing on the ends of his arm hairs. He slowly moved his gaze down as Karen brushed a hand against her cleavage, pulling back the flap of her shirt ever so slightly to reveal the soft skin of her upper breast. Jamie could not help but look, and made no attempt to hide it.

“You’ll kiss your mommy before you go young man.”

She tugged his arm down toward, bringing his upper body with it. With a slight lean upward, she wrapped her fingers through his hair and awkwardly pulled her lips against his, holding the kiss longer than he expected. His hormones raged, as the slight movement on his thigh protruded to a shaming length off his pant leg. She released the kiss and he stood erect, making a quick attempt to adjust the urges of his body. Karen looked down at the pant leg as he avoided eye contact.

“The next time you see me, you call me mommy.”

Monday morning I dragged myself to work, 24 hours ago I thought I would be in a great mood following my weekend with Kim, was now the worst I have ever felt. First, Kim and I confess our love for each other then she proceeds to tell me that she is moving out of town and we will not be seeing each other again. Then, I return home and find a note that my wife, Debbie, had left me for a woman, we had been together since high school and she leaves me a note, how fucking horrible.
I went up to my office and did not want to see anyone, I also did not want to tell anyone about Debbie it was too soon and I did not want to talk about it. Unless the whole office knows because the woman she left me for was Linda from our accounting department. I also could not say anything about Kim as we kept our relationship a secret except for a few of her friends that she told about us or had seen us together. I tried to immerse myself in work to keep me going but it was not working. I had also made a decision to stop fucking all of the girls that I had been in the office. I know most guys that have their wife leave them would chase as much pussy as possible but I had found that all of the random fucking had left me empty and I was wanting more. That was what was so great about Kim was our connection, the sex was fantastic but it was the time together not having sex is what made it so special. I was determined to take it slow for a while.
With that thought running through my head I looked up from my desk when I heard a knock on my door, it was Courtney my intern, “Hey boss, was wondering if I could meet with you over lunch and discuss whatever comes up” she said, as she licked her lips and played with the button on her blouse. Fuck she looked hot, her blouse was black silk that clung to her thin frame, you could see the outline of her nipples pressing against the fabric and she had the top three buttons undone and a long pearl necklace that hung down between her breasts. She was also wearing a tight skirt that was mid-thigh length, the material clung to her young, thin fit ass and legs but stretched when she moved. She came into my office and sat on the edge of my desk and spread her legs in front of me making her skirt slide up to her hips and giving me a view of her bare pussy, she rested one foot on my crotch.
There could not have been a sexier creature ever in front of me. A few days ago I would have shut the door, right then and fucked her good and hard. Now I was in such a bad place I did not get hard with this ravishing creature in front of me. “Courtney, sorry but I just don’t think I am up to it today. You look so beautiful and sexy, but I just can’t. Any guy would be lucky to have you but I am so sorry I am not up to it” I said in a somber tone.
“It is obvious you are not up to it” She said looking at my crotch and her foot rubbing my limp dick. “Let me know if you change your mind, I sure would love to wake up that big cock of yours” She walked out the door and god did her ass look great in that skirt. For a moment I questioned my decision thinking I should just take her out of the office and fuck every sweet tight hole of hers all day long. But I just thought better of it.
I made it through the day, trying to avoid seeing Kim as I knew it would be tough. At the end of the day I was leaving and stopped to talk to Vicki our receptionist that is a good friend.
“I was shocked to hear that Kim put her notice in and is moving, and isn’t it odd that Linda up and quit and just did not show up today, did you hear that” Vicki said to me as I came down. “You don’t seem like you are feeling that great, everything ok?” She said in a concerned tone.
Vicki and I shared most things but I did not ever go on with her about all of my relations in the office and she never let on that she knew from any of the women. “Yeah, Kim told me she was leaving, I am real sad to see her go, we had gotten pretty close” I replied not wanting to say too much out of respect to Kim. “I also knew about Linda, I found out about that yesterday when my wife left me, to go live with her” I had to tell someone and Vicki and I are close, it felt good to say something.
“Holy shit, you are kidding aren’t you?” Vicki said totally stunned
“No that is the truth, they met each other a couple of months ago at a dinner we all went to and they had been seeing each other regularly, I did not know how regularly until last week, and then Debbie said they were going away together this past weekend. So I went away with a friend for the weekend and when I came home all of her stuff was gone, and she just left me a fucking note, a fucking note, do you believe it.” I still could not believe it as I said it.
“Shit, I thought I had a bad weekend, my boyfriend broke up with me. I really did not feel like coming in today I felt so crappy about it. But I think you have me beat. At least he didn’t turn gay on me, at least I don’t think he did” She said jokingly.
Hearing her make a joke about it made me smile. “Sorry to hear that, what kind of an idiot would break up with you. You are beautiful, fun, intelligent, you are just wonderful.”
“Thanks, you don’t have to say those things. Do you want to go get a drink and drown our sorrows together” Vicki asked
“I could really use one, glad you asked, and I do mean it he would have to be a fucking idiot to break up with you” I replied, we agreed on a place to meet and headed out. I did mean the guy would have to be an idiot to break up with her. Vicki has long blonde hair, the most beautiful blue eyes I have ever seen, she is at the most 5 feet tall but is real fit and has the most perfect ass I have ever seen and firm small breast that are the perfect size for her petite build. I had wanted her since the first time I met her but she was usually in a relationship and when she was not she made it clear she would never want to date a married man. This left us in the friend category but our friendship grew over time.
I get to the bar a few minutes before her and ordered drinks for both of us, we had been out in a group before so I knew what she liked. She came running into the bar and gave me a hug. She looked as good as always wearing heels, tight black pants and a tight blue t-shirt that perfectly complimented her eyes.
That night we drank allot for a Monday night, but we had fun and bitched about our relationships enough to make both of us feel better. We drank more than I thought and we ended taking a cab back to her place because she was only 5 minutes away. She got a pillow and a blanket and tossed them on the couch. “You should be pretty comfy there, I will see you in the morning, thanks for being there tonight.”
“No, thanks to you I feel much better having someone to talk to” I replied. We hugged and she gave me a quick kiss on the cheek and she went upstairs to bed. I thought to myself how different she is, all of the women I have been hanging out with would have had my dick in their mouth by now. Not that I did not really want her to, but it was a nice change.
That morning I woke early to hear Vicki moving around in the kitchen, she was wearing sweat pants and a baggy t-shirt she looked cute and sexy. “Sorry did I wake you, I can’t help it, I get up early every day, just can’t sleep in” She said. I sat up “No problem, I like to get up early but I do admit I do feel a little hung over” I replied.
“Were you hot last night, sorry about that, I like it warm in here, I noticed your shirt is off” She asked.
“Oh yeah, sorry, I have trouble sleeping fully dressed, my shirt is not all that is off” I said looking at my pants laying on the floor. “You might want to turn around while I throw my clothes on” I realized that I had my usual full morning erection and just my boxers on which did not hide my huge bulging thick cock.
“I am not embarrassed, why are you” Vicki replied edging me on.
“No, not at all” I answered and pushed off the blanket and walked across the room with my large bulging cock leading the way. I proudly stood there facing her for a moment so she could take a good look and imagine what I was hiding.
“Holy fuck, I heard a rumor that you had a big cock but from that bulge I don’t think the rumor does you justice” Vick said walking closer to me. “What do you think now” I said as I pulled down my boxers and released my massive thick cock that was begging for attention.
“Steve, I really like you, but I like to take things slow, and I think we need to, so I don’t want to go too far right now, if that is OK with you?” She asked looking up at me with her beautiful blue eyes and grasping my cock in her small hand. I leaned down and kissed her. She is so tiny and petite, I was used to her in heels and with her walking around now at her house just made me more attracted to her. She led me to the couch and we kissed deeply and she stroked my cock. I caressed her perfect little ass and gently touched her breasts through her shirt, she was not wearing a bra and this aroused her nipples. We never broke our kiss and she kept on stroking my cock. I went to slide my hand under her shirt, I really wanted to see her small breasts and perky nipples. “No, not yet, let me just take care of you right now, lean back” Vicki asked and I responded leaning back against the couch and pushing my cock up as high as I could. “Wow you are so big, my hand looks so small around it, does that feel good?” she asked.
“Yes that feels wonderful” I replied just laying back enjoying the attention and the sensation of her massaging and stroking my dick. She increased the pace of her stroking and started massaging my balls with her other hand. “You like that, I want to finish you” she said rubbing a little faster. “Oh yes, a little more that will do it, a little more” I moaned and finally exploded, a huge amount of cum shooting up in the air and all over my stomach. “Wow you did like that, let me clean you up” Vicki said as she went into the kitchen to get a towel. I thanked her and we kissed again, grabbing another feel of her firm ass. She told me that was enough for now and I dressed, she made me breakfast and I called for a cab to take me to my car so I could go home to shower and change before work.
That day I was feeling better, I made a point of going to see Vicki a few times during the day which made up both happy and I surprised her with a big bouquet of flowers that were delivered to her home that evening. We started dating like real dates, dinner, movies, shopping just usual stuff. Not meeting up and fucking like crazy like I was used to. But it was great, she made me happy just being with her and I had made it clear to all of the other women in the office that I no longer was going to see any of them.
It had been about a month that we had been dating and we still had not had sex, Vicki a few more times jerked me off but I never got past touching her over her clothes. I did not mind as our relationship was really building and I did not want to ruin it. It was finally her birthday and planned on taking her out for a nice dinner and had gotten her some gifts. I picked her up at her place and she looked fantastic. She was wearing a tight black dress that was short, like not much over your ass short, and a low v-cut that had her small firm boobs pushed up to show some cleavage. Her long blond hair flowed over her shoulders and down her back. She had 4 inch heels on that made her tan bare legs look extra sexy.
“Wow, you look beautiful” I exclaimed. “Happy birthday” I said handing her a bag with a few small wrapped boxes.
“Should I open them now” she said blushing. “Yes please do” I replied. She sat and opened the gifts which were matching gold and sapphire ear rings, necklace and bracelet. She had a tear roll down her cheek. “Is there something wrong” I asked. “No they are beautiful and I love them. I just never had anyone buy me something so nice before, I really love them” she answered quietly. “I thought the sapphires would be great with your blue eyes, let me help you with the necklace” I answered and continued “You have been there for me and are such a great friend, and over this past month you have grown to be more than just a friend, I am a little scared to say this but I love you” in a very nervous tone. Vicki smiled and hugged me and kissed me deeply. “I was scared to say it. I love you too” she said now smiling and kissed me again.
“Ok let’s get to dinner” I said as we got up and headed out “Damn you look amazing” I pronounced as we walked towards the car with her perfect ass in that short dress teasing me.
We ate and talked all night, she kept staring at her presents and never stopped smiling. Seeing her this happy made me happy. Vicki suggested we go back to her place after dinner rather than going to a club like we had planned. She said she just wanted to be with me tonight. I was fine with that. All the drive home I had trouble focusing on the road because she looked so hot sitting next to me in her short little dress, I was so hard. We got to her place and I sat on the couch and opened a bottle of wine while Vicki got some glasses. When she came over to me she put the glasses on the coffee table and surprised me by sitting facing me on my lap with her legs on each side of me. This made her dress ride right up over her ass.
“Oh I feel all tingly inside” she said as she kissed me. My one hand went right to her bare ass cheek, she had on a black thong and the other gently rubbed her breast. She whispered in my ear “Unzip me” and I pulled down the zipper in the back of her dress allowing her to pull it off over her head revealing a black push up bra and a good view of the thong. She slid closer on top of me grinding her pussy against my hard cock. She reached behind her and unfastened her bra and tossed it on the floor. I had been fantasizing about her breasts since our first morning together and here they were now staring at me. They did not disappoint. Perky B sized breasts that were firm but had some sag now that she is in her 30’s. Medium sized light brown nipples that were just right sized for her tits and they protruded out over an inch, god I love her little tits.
“Do you like them, I worry they are too small, sorry about not letting you have them earlier” Vicki said looking down at her tits and cupping one in her hand. “They are perfect, they are really perfect for you I love them and I love you” I kissed her and felt both of her breasts pulling on her nipples. I then had to suck on them. Touching them and sucking them was getting her so excited she held my head against them you could tell how sensitive they are and how it excited her, the whole time she was grinding her pussy against my cock. It was far better than any stripper could do and it was getting her off. She finally moaned and held me tight as she tensed and came.
“Wow I haven’t done that before, that felt real good” she sighed. “And look you are still fully dressed, we need to do something about that” I took off my shirt and she worked on my pants. She pulled them off onto the floor which left her kneeling in front of me, my massive hard cock staring her in the face. She grabbed my dick with both hands and guided it towards her mouth. She placed the tip of my cock in her mouth and was gently stroking the base of my cock with one hand. “It is so big, I can’t take more of it” She said trying to slide as much of my cock into her mouth. “What you are doing feels great don’t stop it feels so good” I moaned. Vicki picked up the pace of her sliding my cock into her wet inviting mouth, soaking my cock in her spit and stroking the wetness over the full length of my shaft. The whole time she stared up at me with her big blue eyes never breaking gaze from me. I stroked her long blonde hair away from her face as she worked my cock in and out of her mouth. She stopped sucking me for a moment to catch her breath but feverishly stroked my cock with both hands. “Oh wow you are going to make me cum, please don’t stop” I pleaded. “Come on baby, give me your cum, I want to make you cum” Vicki said as she slid her mouth back onto my cock. That was all I could take and exploded, shooting out more cum than I can ever remember, I shot it into her mouth onto her face into her hair and onto her chest. Vicki looked up at me and smiled, looking proud that she made me cum so much even though she was covered from my explosion.
“I am going to go get a towel” she said as she got up and walked to the kitchen. This was the best view I have had of her as she got up and walked away only wearing her thong, she is so petite, fit and her ass is perfect. I was feeling so happy and satisfied and wondered to myself if we were finished for the evening, I wanted more of her but I also know we had been going slow so if this is all she wanted I was fine with it. “Wow you really made a mess of me, I am going to go take a shower” Vicki said as she walked towards the stairs to go up and shower. “Ok that sounds good” I replied. “Well why are you sitting there, I was hoping you would join me” she said as she ran up the stairs, I hopped up and chased after her.
When I got to the top of the stairs she was waiting for me now naked holding her thong in her hand, revealing a small, well groomed landing strip and her bare pussy. She has big pussy lips that I could clearly see hanging down between her legs, which was clearly visible because her legs are thin and fit leaving a clear gap between them a good view at her pussy. “You are so beautiful” I said pausing to take in her beauty, seeing her naked for the first time, all she had on was the jewelry I gave her earlier in the evening. “Thank you, get over here” she said as I walked over and hugged her. My body engulfed her, she is so tiny and petite, probably not even 5 feet tall and I am almost 6-4. I loved holding her. “Come on let’s get in the shower” She said taking me by the hand. We stood there kissing as we waited for the water to warm up and went into the shower, she looked even sexier with her hair and body wet. We soaped each other up, her body felt so good as I ran my hands over her breasts and she grabbed my big half hard cock and slowly stroked me. I leaned down and kissed her and reached down and placed my hand on her pussy, Vicki pressed her body tight against me and moaned with pleasure “That feels so good, oh that feels good” It felt good to me too, I dreamed about touching her pussy and now I finally had her and she was reacting to my every touch enjoying every moment. She broke away from me for a moment and sat on the built in bench in the shower and spread her legs wide having the water rinse the soap from her body. I dropped to my knees sucked on her nipples and touched her pussy, rubbing her clit. “Oh that feels amazing” she moaned. Needing more she gently pushed my head down to her pussy which is just what I wanted. I ran my tongue up and down her big lips and into her little hole and then attacked her clit with my tongue, this was driving her crazy as she held my head tight against her moaning louder and louder. I slid both of my hands up onto her breasts and played with her nipples. This was more than she could handle and she came hard shaking and her pussy oozing with moisture. I looked up into her blue eyes and she was smiling. I stood up and held her against me pressing her head against my stomach as she was still seated on the bench. My cock was now fully hard and stood out right next to face.
Vicki grabbed my hard cock and stood up and shut off the water. “Come with me, I need to be with you” She said as we stepped out of the shower, toweled off and headed toward the bedroom. We stood next to the bed kissing and she pushed me back onto the bed and crawled on top of me. “I wanted to do this since that first morning I saw your cock, but I wanted to make sure of our feelings, I am sure now and I really want this” She said as she crawled on top of me grabbing my cock and sliding it into her pussy. She just eased the tip in as she is so tight and had trouble stretching around me. “I have never had such a big cock inside of me, I don’t know if I can take it” She said, I could feel her entire body tensing from her anxiousness about being able to take the girth of my cock.
“I love you, I have dreamt of this moment from the first time I met you when I came in for my interview. I left the building that day hoping to get the job because I wanted to know the beautiful woman with the most spectacular blue eyes” as I told Vicki this I had slid my hands on her hips and helped ease her down on my cock as I thrusted slowly up into her. “I love you too, and oh fuck are you big” she replied. Her pussy now stretched over me feeling warm, wet and wonderful around my fully engorged dick. Now fully inside of her I sat up and kissed her deep and hard our tongues locked together and holding her tight as she adjusted to the size of me in her pussy. I could feel the tension she had in her body release as we kissed and she started to grind against me.
“Oh fuck that feels so good now” Vicki moaned as she pushed me back down on the bed and started sliding up and down the full length of my shaft ever so slowly at first and gradually speeding up. “You are so beautiful and this feels so good” I said as I thrusted up into her. I played with her breasts and pulled on her nipples, the sensation of this made her moan louder and drive up and down on me faster. She is so small and looked so sexy with her long wet blonde hair as she rode me I never wanted this to end. “Hold on a second, how about like this does that feel good, oh fuck you are hitting me with your cock perfect oh fuck yes” She yelled as she had slid me all of the way in and spun around on me know facing away from me riding me reverse cowgirl. This gave me a perfect view of her little tight ass and my cock sliding in and out of her pussy, I grabbed her ass and helped her slide up and down my length. She started rubbing her clit with one hand “Yes, yes that is perfect, oh fuck yes, give me all of your cock oh fuck yes, I am going to cum, cum in me Steve of fuck cum in me” Vicki screamed now in a fury riding my cock. I pushed hard up into and came deep in her pussy and at the same time she shook having a long deep orgasm. Vicki slid off of my cock and laid next to me with her head on my chest and I held her tight. We stayed like this for almost half an hour hardly saying a word, I was caressing her head and back as she gently touched my stomach and groin area, just enjoying the feeling of our naked bodies together. She finally slid up and kissed me deeply, started stoking my cock and whispered in my ear, “Can you do it again, I want you to fuck me again”
“I want nothing more in the world” I replied and kissed her again sliding my hand on her wet pussy, she spread her legs wide inviting me to give her pleasure. I easily slid two fingers into her inviting pussy, still stretched from receiving my cock, and I rubbed my thumb on her clit. She arched her back and let out a loud moan of pleasure, I moved my head down to her breasts and started sucking on her erect nipples. “I want your cock, bring it up here I can’t reach it, I want to suck your cock” she begged. I knelt with one leg on each side of her body and placed my half hard cock next to her inviting mouth. I reached my hand back down to her pussy and slid my fingers back into her making her moan as she grabbed my growing cock and slid it into her mouth. I propped her head up on a couple of pillows so I could drive my cock straight into her inviting mouth. I was not yet fully hard so Vicki was able to take more of my cock, I pushed my dick down into her mouth and held it still allowing her to take as much as she could handle and she was loving it. Sliding her mouth over my shaft and rubbing my cock and balls with her hands she was totally into my dick and wanted it all. All of the time I was persistent with fingering her pussy and rubbing her clit. Her satisfaction with this was growing I could tell from her intensifying moans while trying to swallow my cock. She finally released me from her mouth and yelled “Oh Fuck!!!” and came oozing juice all over my fingers. I thought to myself that I had never been with a woman that could orgasm so easily.
By this time I was hard again and I wanted to fuck her tight pussy. I slid down her body and pushed her legs up and down towards her chest so she was bent in half and gave me clear access to her pussy for my now throbbing cock. She started up at me with her big blue eyes and muttered “Please fuck me, I want to feel all of you in me please give it to me” With that I slid my cock deep into her, not being so patient this time and driving my shaft in balls deep. She was so incredibly tight around my shaft and was so wet and warm, it was perfect. “Shit you are so big, give it to me I want it all, I can take it give it to me” she moaned but wincing as I drove slowly in and out of her. “Let me know if I hurt you and I will stop, but I am going to give you all of me” I said as I started pounding down into her sweet pussy. I was hitting her hard and giving her my full length, making loud slapping sounds of my body smacking down into her pussy. “Oh fuck yes, give me more don’t stop” she yelled as I thrust hard into her. “Keep going I want you to make me cum like this, oh fuck don’t stop” I kept pounding her I was dripping in sweat from my effort and she just kept urging me on until she let out a loud scream and came one more time. I collapsed down on her and kissed her, both of us sweaty and hot and with my big hard cock still inside of her.
“Take me from behind, I bet that will make you cum” She said excitedly like making me cum again was a challenge. She rolled out from under me and positioned herself on her knees on the edge of the bed so I could stand behind her. Vicki’s ass is perfect especially from behind and her pussy was swollen and red, her hole gaping open from the repeated penetration of my cock. I stood behind her and shoved my big cock into her inviting pussy. “Oh yeah, fuck me that feels great fuck me give me you cum baby fuck me” she groaned as I drove hard into her, knowing that if I was going to cum again this is how I would be able to do it and I would have to give it to her hard and fast. “Pull my hair and spank me baby I want you to fuck me good” she demanded. I did as ordered and grabbed her long blonde hair into a pony tail and yanked back on her as I fucked her hard and slapped her on her ass until her cheek was red. I thought to myself this is the same woman that abstained from sex for over a month other than a couple of hand jobs and now she was getting wild and loved my hard fucking of her little pussy, I was surprised.
“Cum in me come on give me your cum” she begged as I pulled on her hair and I pounded into her from behind. Finally after a few more minutes both of us now totally wet with sweat I released inside of her and collapsed on top of her on the bed. The rest of the night we showered again, I ate her pussy in the shower once again because she said it felt so good the first time and we went to bed in each other’s arms our naked bodies entwined as we slept.
I woke in the morning alone in bed, naked and with my usual throbbing morning hard-on. I found my boxers and pants at the foot of the bed that I had left downstairs the night before. I slid on my boxers and that was it as it was warm in the apartment. I waited a moment and went in to the bathroom so my cock could get an opportunity to go down. I did not want to look like a total horn dog running down the stairs being led by my huge hard cock.
I made my way downstairs where Vicki was standing in the kitchen waiting for coffee to brew and looking at her tablet. “Good morning, you look as beautiful as always” I said as I walked over and gave her a deep kiss. She looked up at me and smiled, and she did look beautiful and incredibly sexy. All she was wearing was my dress shirt from the night before, she had the sleeves rolled up and the top few buttons undone so she was covered walking around but I could get a quick glimpse of her naked breast when she moved. The shirt was big enough on her petite little body to go down to her knees. “What are you smiling at” she said giggling at me as I just started at her beauty and sexy little body. “You look so sexy in my shirt, I am such a lucky guy” I said as I walked to her, kissed her and put my hands around her thin waist. “Oh, thanks” she said blushing, “I guess you do find me sexy” she said as she reached down to my now hard cock”
She let go of me and boosted herself up on the counter and undid the bottom few buttons of the shirt and opened it up to give me a great view of her little tits and well groomed pussy. I moved in close to her and we kissed, I slid her ass to the edge of the counter which was the perfect height for me, I pulled down my boxers and slid my cock into her inviting warmth making her gasp in surprise, she was now getting use to my girth and she was dripping wet so my cock gained easy access to her warm wet hole. We kissed the entire time we fucked and I held one of her breasts and played with her nipple which she enjoyed so much. She reached a hand down and rubbed her clit and could feel my shaft sliding in and out of her. We fucked and she rubbed her clit until she came and she felt so good to me I never slowed for her through her orgasm. Vicki whispered in my ear “When you are ready I want to taste your cum, I want to swallow all of you” I said nothing, just kissed her and sped up my thrusting into her wetness. We never broke from our embrace for another couple of minutes until I knew I was going to explode. I pulled out of her and stepped back, Vicki jumped off of the counter and dropped to her knees as I stroked my cock. I released my cock when she grabbed it and placed it in her mouth driving me to completion shooting my full morning load into her mouth, making her gag but she swallowed every last drop and licked me clean.
My shirt fell off of her shoulders to the floor when she stood up and we hugged, it felt so good to have her naked body pressed against me. “You still have your jewelry on, it looks great on you.” I said to her as I lifted her back up onto the counter. “Yeah, I love it, I am never going to take it off, and I will let everyone know that my boyfriend that I love so much gave it to me” Vicki said proudly. “Well your boyfriend loves you too. Who knows someday you might get a ring to match the set” I said before I realized what came out of my mouth. “That would be wonderful” she replied and kissed me.
After a few months I had my divorce finalized with Debbie, it was very amicable as we were both in love with other people and just wanted to move forward with our lives. Vicki and I moved in together after I sold my house from my marriage. She was fantastic to livre with, she was constantly horny and wanted sex all of the time. It was hard to believe that we dated a while without sex because she was so crazy about fucking. We both liked to wake up early in the morning every day and fuck before we went to work. After living together for a month or so I proposed to her on Valentine’s day and we were married the following summer. All of the other women that I had over the past year were understanding of my relationship with Vicki and once they knew of our situation they accepted it.
I ran into Becky one night when we were out and she was now dating someone and was happy. Angela had gone through a few boyfriends, she is good friends with Vicki, and one drunken night she told her that she can’t find a guy with a cock big enough to make her happy. Lena is happily by herself and says found god, but still has Lisa spend the night with her every once in a while. Lisa said she does not feel guilty cheating on her husband when it is with another woman. Tina has found another guy to fuck her at lunch time, I can always tell when she comes back to work when she met with him. Sue is still a total slut, she is not shy about telling me of her sexual adventures and occasionally checks to make sure that I don’t want to fuck her with my big cock. Ashley is still a good friend of mine and she has found a boyfriend I will always watch out and care for her. I heard from Kim a couple of times after her move and she finally told me that she could not contact me anymore as it hurt her too much to talk to me and to not be with me. I wish her well and I hope she finds happiness. Katie got married, she found a guy from what I heard that has a good size dick and just wants oral sex. Katie fell in love. Christine took a job at another company a few weeks after the time we fucked and I never saw her again. Debbie and Linda were married a few months back, now that gay marriage was legalized in our state. They are both very happy we stay in touch on a regular basis. Yan was brought back to China by her parents and did not finish school here. She found such a taste for American cock that she was doing every guy she could on campus. She got pregnant and when her parents found out they brought her back home. Courtney finished school and got married right after graduation. She was fucking a 45 year old wealthy real estate developer that left his wife and kids for Courtney’s tight little ass, she is now a step mom to 15 and 13 year old boys.
All of these women were such an experience and allot of fun, but I am so much happier with just Vicki, I could not ask for more. Besides that I don’t have ass prints and pussy juice on my desk anymore.

Long time lurker. Throwaway for reasons that will be obvious later. This is a story that I’d likely take to my grave were it not for this subreddit. Even though I don’t condone what happened, I want to write this story down lest the memories and details fade. There’s a fair amount of buildup to give some context, so bear with me. Names have been changed to protect the innocent and the guilty. Jump to the break for sexy times. TLDR: met a chick who was a friend of a friend. Grappled with moral conflicts and had the best sex of my life.
I moved to a new city at the start of 2016. This story had its genesis not long after that when my buddies who live semi-close organized a ski trip for a bunch of friends, and I tagged along, not knowing too many other people in my new city. One of my buddies was dating this girl named Lanh (no, the story is not about her), who hung out with us all the time, and was pretty much another guy in the group. Lanh had a large contingent of Vietnamese friends that we knew in passing through her, and frankly, my buddies and I weren’t too thrilled to be sharing the cabin with all of them as they tended to keep to themselves and always took forever to reach a group consensus for everything.
Lanh’s car had arrived at the ski cabin before ours did, so by the time we arrived, they had just started eating. When I walked into the door, there this mystery girl was, about 5’5” and 110 lbs, standing by the dining table in a white tanktop and jean cutoff shorts, with a very enticingly petite figure. Our eyes locked for a split second before she sashayed off to the kitchen to grab more food, and I set my bags down for a meet-and-greet with the other people already there. Her name was Mindy. She was actually one of Lanh’s good Vietnamese friends and I had heard of her name, but we had never met in person. I got to talk to her on and off throughout the night, and she was a very sweet girl, funny, and shared similar tastes in music. I found her attractive both physically and intellectually.
But … I was in a long term relationship and was engaged to be married in a few months, so I didn’t think too much about it at the time. My fiancé didn’t want to move to the new city immediately in order to wrap up work and spend more time with friends and family, so I was feeling a bit lonely.
(If you’re wondering about me and my sexual history, I’m a pretty average looking Asian guy with a high sex drive, never really had trouble getting dates once I got over my shyness of asking girls out, but have only slept with a white girl and a half-Asian girl.)
The group spent the days skiing and the nights pretty much were for eating and drinking. Nothing of interest to this subreddit happened on the ski trip itself, except there were two events I want to briefly mention. The first was that one of the people that I didn’t know found out I was getting married in a few months. He, drunkenly, poured shots for everyone and said we were celebrating the end of my bachelorhood. So everyone, Mindy included, knew I was getting married.
The second was on the trip back: because we had different plans to return home, I ended up in the van with Lanh, Mindy, and their friends. As I was about to doze off in the back, my phone vibrated. It was a text from Mindy saying she had a great time hanging out with me and my friends, and she was disappointed that she wouldn’t know when she’d see me again. We texted pretty innocently back and forth about our lives, dreams, other musical interests, our shared love for basketball, etc. until my phone died (though in hindsight the initial text may not have had innocent intentions).
A few days later, my hometown NBA team was scheduled to play in my new city, and since the new city had a top-notch team, I thought it’d be fun for an outing with any of the new friends I made. The only affirmative response I received was from Mindy. I was able to get decent seats for a very reasonable price, so I figured it’d be a nice gesture to just treat her to the game and not have the mood ruined by awkward discussions of who’s paying what later.
We met at a subway station near her work that evening, and our interactions were noticeably more light hearted and flirty. She reached for my hand as we walked to the arena, and I thought I’d indulge her and let her enjoy the experience of going to this game, especially seeing how she dressed to the nines as girls tend to do for sporting events.
We made a bet that if the home team won, she’d get three wishes, and if my team won, I’d get three wishes. Even though it was a slightly unfair bet, given Vegas made the home team a 20 point favorite, I agreed, again wanting to make it a good time for her. The game was tied after three quarters, and we were both freaking out that I might win the bet. Alas, the home team did what they always do, and buried my team by 20+ points by the end.
I saw her off at the train station closest to her apartment, and we parted ways after a hug that lingered for a few extra seconds. After that, our texts moved from flirty to innuendos, to hints of what turned us on in a span of a few days. I still told myself that it was flirtatious fun, and secretly enjoyed the attention.
One night, she sent a ten second video of a really grooly pussy and a finger noisily dabbing at it, with the caption “This is what you do to me.” I furiously jerked off, and right before cumming, I got the idea of recording the last few seconds. It was a gloriously explosive finish, and against my better judgment, I made sure to moan her name out, and sent her the video.
The following day, she texted me, “My first wish, is to make dinner for you, and watch a movie afterwards. This is part of our bet.” Still telling myself “it’ll just be dinner and a movie” we agreed on the following day which was a Thursday.
That Thursday, she came over, made dinner, including a few dishes that were her specialties which she had told people on the ski trip. I cracked open a bottle of Riesling for us and we had a very nice meal and conversation, nothing overtly flirty nor comments with double entendres, which eased my worries a little bit.
As dinner wound down, I offered to clean up the dishes and asked her to just sit down for a bit and pick out a movie, but she spent a good 20 or 30 minutes in the bathroom. She came out of the bathroom in a white nightgown that showed her shoulders, clavicles, and it came down to about mid-thigh.
My jaw dropped as she looked like an angelic vision floating out of the bathroom, and we settled back on my barstools. As we were sipping on our wine, she started asking me about how my first kiss happened, first girlfriend, etc. and we traded stories about our first times. All of hers were tinged with sad unforeseen consequences: she kissed a guy but another friend who was head-over-heels for her was devastated; her first sexual partner was crazy for her, but eventually became so controlling that he hurt her. She claimed that she hadn’t been with any other guy since then.
At this point in the conversation, I didn’t know what else to do other than to try to console her that she deserved to be treated well and be allowed for her talents and aspirations to flourish. We had planned to watch a movie (yeah I know … I was still telling myself that it’d be “just a movie”), so I booted up Amazon Prime (she couldn’t login to her Netflix account) on my computer and inflated an air mattress that doubled as a temporary couch. While we waited, I went to my room and changed into a more comfortable shirt and my pajama pants.
I asked her what she wanted to watch, and she just replied with “Anything.” I think I picked out “The Fault in Our Stars” since I heard it was half-decent, and I thought she’d like that genre to close out the night. As soon as the movie began, she reached for my hand and our fingers started caressing each other. My heart was pounding like a stampede of elephants, and my head was flashing warning signals while my fingers were on autopilot feeling her slender hand. By this point, the sweetness, the intimacy, and the stimulation on my fingers had me rock hard, reminiscent of the high school days of nervous finger caresses in a dark room.
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I heard myself suggest that we lay on our sides, and she smiled and tucked herself in the little spoon position. I propped up my head with my left hand and my right hand was still entwined with hers across her midsection. Not paying much attention to the movie at this point, I could smell her shampoo and fragrance emanating from her hair and neck, and it was oh so soothing and delightful of a scent. I buried my nose in her hair and just breathed deeply, in and out, in an attempt to slow down my racing heart and shortening breaths. I sensed her nuzzling my cheek with hers as she slowly tilted her head towards me. I looked down at her, saw her eyes twinkling as she smiled at me, and thought “uh-oh what am I doing?” right before our lips met and we kissed slowly, sensually, and firmly for the first time.
We kissed again, and again. The dialogue and sounds coming from the movie were starting to be distracting, so I reached over her and hit the pause button. She was on her back now, and we resumed kissing, my right hand stroking the petite curves of her waist outside of her gown. We kissed like this for a few minutes until she took my right hand in hers, and moved it up onto her breast.
“I want you to explore my body,” she whispered. Emboldened, I gave each of her firm breasts a gentle squeeze, and heard soft purrs emanate from her. I slid my hand down the top of her nightgown, and grasped a naked breast (a large B cup that looked ripe and luscious on her small frame), feeling the smoothness of her skin, the firmness of her breast, and her nipple that was fully at attention. She had these beautiful nipples, about as wide as a dime and stood up prominently, almost like the teat of a pacifier. She gave more of these sexy sighs into my mouth as I played with her boobs.
Horniness was firmly in the drivers’ seat now. I pulled my hand out from her top, and slid it down her side to her knee, then reversed direction along the inside of her leg. My progress slowed down as I approached her inner thighs under the hem of her gown. She started to whimper as I got closer and closer to her most sensitive places. I reached her bikini line, and as I caressed up to her pelvic bone, I gasped a little, feeling nothing but more smooth skin. The uniform smoothness of her skin everywhere is something I’ll never forget.
“You’re not wearing panties!” I gasped, now thinking back to our time on my barstools. She must’ve sat on them on her bare ass and I had absolutely no clue. She didn’t say anything back, just moaned “Mmhmm” as she brought one hand to the back of my neck and brought me in for another kiss.
Curiosity pushed me to slide my right hand back down, this time straight down the middle of her body. Not a single hair or stubble was in my way, and I groaned in pleasure of feeling her smooth, perfectly shaved and waxed pussy. (Guys, it’s totally true that women decide when they’re going to have sex with you.) I love the feeling of a shaved pussy, and all of my previous girlfriends were full-bush. My fiancé at the time completely waxed the first time I saw her naked, but has let it grow ever since then.
My middle finger slid down along her clit and ran along her lips. Oh. My. Fucking. God. Was she soaking wet. To this day still, that was the wettest pussy I have ever touched (out of the half-dozen or so girls with whom I’ve fooled around). The best description I can give is that I imagined her juices formed a bubble along her slit, and when my finger touched it, the surface tension broke, and the liquid flowed everywhere. Her entire genital area seemed to be flooded right after my finger passed.
I immediately started giving her full length strokes along her lips up to her clit, on which I’d run gentle little circles. No more than three strokes later, she took my hand and shoved my middle finger inside her, groaning as my digit penetrated her. I plunged into her firmly, but not too fast, rubbing her upper wall whenever I could. She reached back, and felt my hard-on through my pajama pants, and wasted no time sticking her hand in to grasp my penis. Her little fingers felt so good as she slowly stroke the length of my shaft, not too hard, which I appreciated. Her ministrations had me at full mast (sorry this is not a porno … I’m average sized, about 6 to 6.5 inches when fully erect).
Not long after, I felt the urge to treat this girl, and blurted out, “I want to taste you,” as I sat up and kneeled between her feet. She spread her legs, and I got my first good look at her beautiful innie pussy glistening from the streetlight peeking through my window. I gave her a deep lick from the bottom of her slit to her clit, tasting her most sacred place. It was delightfully clean, fresh, with just the slightest hint of arousal.
I plunged my middle finger back into her and simultaneously curled my finger and drew circles and the alphabet with my tongue. I felt like I was in heaven already, pulling out all of my tricks to please this girl. My fiancé always adamantly refused to receive oral, something I actually enjoy doing. Mindy, though, I could tell, approvingly held my head in both hands and I could hear just the cutest gasps coming out of her.
I kept up the tongue and finger treatment for about 5 minutes until she shuddered ever so slightly and yanked me up to give me a kiss.
“I told you you could make me cum really quickly,” she gushed, in reference to one of her racier texts, and kissed me as I beamed with pride. “Now it’s your turn!” And with a giggle, she pushed me onto my back and swung her leg over and mounted me. I was still fully clothed at this point, but she pulled on my shirt and started kissing my chest slowly down to my stomach. I keep in decent shape, but my abs don’t really show unless I flex them, so I did a half-crunch for her, and she kissed my abs.
She hooked her fingers into my waistband, and coquettishly asked, “Should I stop?” I looked at her devilishly smiling at me, and thought about how I was in a long-term relationship. “Should I stop?” she asked again. I laid back down, the white angel on one shoulder yelling at me and making my boner dissipate. “Should I stop?” she asked for the third time. Since this is /r/gonewildstories, I told myself that “maybe this will just be a blowjob.” I lifted my hips up and she pulled my pajama pants and underwear down to my ankles in one go.
“Ohh…” I heard her say disappointingly. My engines were only at quarter-impulse after the brief battle with the white angel, something she probably wasn’t expecting to see after all we’ve done.
“I’m sorry, I’m just really nervous,” I told her sheepishly. “It’s ok, just lay back,” she replied. God bless her.
She proceeded to kiss my thighs and abs while she held my semi-hard dick in her hand. As I grew harder again, she peeled back my foreskin, and placed little kisses on my tip, before enveloping the head into her mouth. She did this thing where she alternated between swirling her tongue all around just the head of my penis, and then bobbing my head in and out of her lips which made a soft whoosh noise each time. It felt insanely good and I was hard as steel again in no time.
Despite how good it felt, she never took more than maybe three inches of my cock into her mouth. I usually need more stroking in order to cum, which I could have told her, but I didn’t want things to end. My extremities were tingling from her efforts, yet I knew I wasn’t going to cum anytime soon (any other guys experience this??).
Insanely horny and lightheaded, I asked her, “Are you on birth control?” She pulled her lips off my dick with a wet plop, scrunched her nose cutely, and whispered sadly, “No … I’m not sexually active.” Upon hearing that, some primal part of me felt really excited that she was opening herself sexually to me, but another part of me was relieved that that was a good excuse to not go any further.
Which was why I couldn’t believe that I heard myself ask her “Should I get a condom?” She kept bobbing her head on my dick and didn’t answer. “I can get one if you want me to. I have some in the bedroom.” Again, she kept sucking on my dick. Feeling as stimulated as I could get without any indication of orgasming, I pulled her up, laid her on her back, and started kissing her again.
I crawled on top of her, kissing her from her flat tummy to her magnificent boobs, to her neck, and finally to her lips again. She suddenly whispered to me, “I will take the morning after pill tomorrow,” and I felt her legs widen to accommodate my frame.
Once again, I became horribly conflicted. The devil on one shoulder pumped up my excitement and base desires, especially with the prospect of bareback sex within reach. (My ex-gf and I always went bare when she was on the pill, and I very quickly grew to crave the intimacy, the sensations, and the primal victorious feeling of cumming inside a woman. On the contrary my fiancé refused birth control, and had never let me even close to her without a condom.) The angel on the other shoulder pleaded that I could still back out, keeping the streak of the same vagina for my penis alive.
I tried to delay that decision for a bit, and being as horny as I was I thought I’d rub my penis on her for some pleasure. I arched my back slightly and she gasped as my penis came into contact with her clit. I pressed down and my dick slid effortlessly down her sopping wet lips.
“Just let me rub against you.” I murmured in her ear, and I rubbed my penis back up to her clit. Then down. And on the upstroke, she must have tilted her hips up to meet me, and my tip wedged in between her lips. Startled, I pulled back and rested near her clit again.
“Just let me rub against you,” I half-begged again. The slippery sensation of her lubricating juices was starting to drive me wild. Down. Up.
Down. “Just let me …” She tilted her hips a little fiercer this time, aligning our respective organs, and I lost all resistance. “… Unnnngh.” I slid all the way into her steaming hot and impossibly slick vagina in one stroke. The sensations of her wondrous, and more importantly, bare pussy felt like an EMP went off and my brain was completely fried. Speech and any coherent thoughts were reduced to that singular grunt I let out. We rested like that, joined at our most intimate parts, for 10 – 15 seconds.
As my brain functions came back online, a million jumbled thoughts ran through my head: “I’m in her. Holy shit she feels amazing. God are we really doing this? So wet, so warm. We’re completely unprotected. STDs? God she’s moving again.”
Then all rational thoughts went out the window, and instinct and passion kicked in.
[I know, I know … with a clear head, I can tell you I should have worn protection with a new partner. It’s weird experiencing in the moment though, like how every investor always says that they would never panic when the stock market tanks 50% in a week, but what does everyone do when the see their account holdings down 50%? They panic sell.]
I slowly drew out of her most of the way and thrust back in. I could definitely feel her cervix at the end of each penetrative stroke, and I made note of how tiny she was and made sure not to hammer her too hard. She undulated her hips, and moved with me in perfect synchrony. I matched her pace and we quickly established a mutual rhythm.
We kissed as soon as we started the mating dance too, and I felt so connected, so in tune with this girl that I met just weeks ago. I pulled her nightgown down to bunch around her waist, so I could watch and fondle her amazing boobs. We made love for 2, maybe 3 minutes max, because honestly, I’d been so turned on this whole time, and my bare penis was being overwhelmed by the velvety grasp of her well-lubricated vagina.
With orgasm rapidly approaching, I managed to gasp out one final warning to her. “Ohmygod… MindyI’mgonnacum… Doyouwantmetopullout?”
She wrapped her arms around my back and whispered in my ear, “No. Don’t stop. Just cum inside me.”
Hearing her say that was the ultimate aphrodisiac, fueled by the knowledge that this lovely girl wanted me to spray my seed inside her likely fertile vagina. I managed two more thrusts, then held my penis inside her as far as it could go, and let loose with a grunt. My dick spasmed and pumped out at least five or six volleys of my semen inside of her. I was seeing stars as we clutched at each other tightly, and I heard her coo contentedly. She would tell me the next day that she came a second time when she felt my dick throbbing and releasing from my orgasm.
I stayed on top of her, locked in orgasmic embrace for a couple of minutes following the best and most passionate sex of my life. We whispered sweet nothings for a bit, like her telling me how full of cum she feels and will need my shirt to catch the spillage. As soon as that high wore off though, the guilt hit me like a fully loaded 18-wheeler.
Wow, this took a long time to write. If there is any interest in the rest of the story, I may write about it in future installations.
P.S. She confirmed after sex that she was clean. I was too, and have since been tested. She also took Plan B the next morning. I’m now (pretty) happily married.