Author: playingmilf

A delightful scene from last night. I am the luckiest girl – MILF

Just really want to share it with someone because there’s no one IRL that I talk to about sex (except my partner). I’ve never written something like this before so I hope it’s worth reading!
A while back we started filming ourselves having sex and that was so fun. Lately we’ve both been working so much though that sex has kind of become a footnote. I took yesterday off work and halfway through the day I was actually surprised to find that I was horny. I went to bed and watched our videos, playing with my favorite vibe and my Christmas gift (a dildo made from a mold of his cock), and then got ready to pick him up from work.
I wore a short dress, a long coat, my highest heels, and nothing else. When I arrived at his work he was outside smoking. I got out of the car to share a few drags and walking back I unzipped my coat and flashed my ass at him. He followed me to the car with a wolf grin and as I buckled myself back in and spread my legs he shoved two fingers in my cunt. He brought me right to the edge of orgasm and stopped, denying my completion. As I drove us home he teased the edges of my labia but wouldn’t touch my aching clit.
As soon as we shut the front door he pounced, pinning me to the wall for a long kiss and then commanding me to sit on the sofa and present my pussy. He kneeled between my legs and ate and fingered me until I was dripping wet and delirious.
“Go to the bedroom. You may not get undressed. Wait for me standing, facing the bed.”
I went and waited, anticipation creeping along my spine, thighs clenching. I heard him enter the room. He placed some items on the table and came to stand behind me. Slowly his hands teased up my thighs and stomach, carrying the thin fabric of my dress as they went. He pressed closer, nuzzling and biting my neck as his warm palms ghosted across my hard nipples. He became impatient, tugging the dress off and pinching both nipples hard, making me cry out with pleasure. I tried to lean forward on the bed for support, but he grabbed my hair and pulled me back to him, sinking his teeth into my neck, one hand still pulling my nipple while the other snaked between my legs to stroke my clit.
“You’re so wet. You’re hungry aren’t you my little slut?”
“Yes Sir. I can’t imagine why, Sir.”
The hand that was rubbing my pussy pulled away and he smacked me sharply on the ass. “Don’t get smart. Get on the bed. On your back. Spread your legs.”
I did as I was told, trembling and dizzy with want.
“Good girl. I’m going to play with your nipples. You may not cum. You will let me know when you are close.”
“Yes Sir.”
He laid beside me, fingertips dragging along my thigh and up my abdomen, pausing now and then to circle back. They arrived at my breast, blunt nails scraping along the swell of the underside and following the curve around the perimeter. I trembled. My nipples were puckered, achingly hard already. But he did not give me relief. His hand moved back down to the other thigh, repeating its progress up the other side. Then, suddenly, he was tugging on one nipple and suckling at the other, scraping with his teeth and soothing with his tongue. I had already been so close and the pleasure was intense.
“Please sir I’m going to cum!”
I let out an involuntary whine as he paused, blowing cold air over my nipples.
“I told you what to expect, did I not?”
“You did, Sir.”
“Are you complaining?”
“No Sir, I promise Sir.”
“Good girl,” he breathed, lowering his head back to my breast and returning to his rigorous assault on my senses.
My hands grasped at the pillows, the bedsheets, his back, and his hair, seeking some kind of stability.
Four more times I had to tell him that I was too close, and four more times he stopped. I could feel my pussy dripping, the sheets damp between my thighs. My cries of pleasure were becoming hoarse. I wanted so bad to beg for my orgasm, but I bit my tongue, knowing that any plea would be met with extended denial.
“You’ve been very good,” he murmured, lips pressing a line along my cheek and neck. “Very good. Would you like to cum?”
YES PLEASE I thought, but remembered myself, “If Sir so desires…”
“Very much.” Once more his hot mouth closed around my nipple, but his hand did not reach for the other. Three fingers pushed inside me, stretching me, rubbing my gspot in hard, purposeful strokes. I screamed in unabashed gratification, feeling myself squirt into the palm of his hand.
“Soooo gooooood my sweet girl.” He slid down the bed, burying himself between my legs, tongue and fingers working in tandem to make me cum and cum for him. He reached over to the table and a moment later I felt him dragging a toy along my slit, coating it in my juices. As his mouth returned to my clit I felt pressure against my ass, the slow thrust of a plug entering me. Every few centimeters he would pull it back out and start over. I bit my lip to keep myself from begging. The more he filled my ass, the emptier my pussy felt. One final thrust and he left the plug in, but he pulled away.
“I think you deserve a little break… I’ll go get you some water.”
He left the room and I repositioned myself on the bed, still on my back with my head hanging over the edge. I wanted a drink, but not of water. I knew I may be punished, but that the pleasure would outweigh the cost.
He came back in with a glass, taking in my new position as he set it on the dresser.
“I didn’t tell you to move.”
“I’m sorry Sir.”
“Do you want my cock?”
“Yes Sir.”
“Want me to fuck that pretty throat?”
“Yes Sir.”
“Want me to feed you my cum?”
“Please Sir.”
“You have been good…. and good girls are always rewarded…” He took his cock in his hand and my mouth dropped open.
“I certainly love that response,” he said, pushing as deep as he could.
I swallowed eagerly as I felt the tip of his cock at the back of my throat. He began a slow movement and I moaned, urging him faster. I love it so when he fucks my mouth. His hands found my breasts again, squeezing and teasing them, sending shivers through me. It’s always so hard for me to focus on my technique when he starts to please me, but I forced my attention back to pressing my tongue against his shaft and flicking it across the head between each thrust.
“Sir has such a good little cocksucker.”
I moaned again, basking in his praise. He pulled his cock from my mouth with a pop. I arched trying to reach it but he lifted it away from me. Tilting my head further back, I took his balls in my mouth instead. This earned a loud groan and a curse. I laved over each testicle with my tongue, devoting attention to each in turn until his thighs shook and he moved away just enough to shove his cock back down my throat, thrusting hard and fast.
“I’m close to cumming,” he warned, but as I increased my efforts to bring him to orgasm he pulled away entirely.
“No,” he said. “No I don’t think I’m going to cum down your throat tonight. Get on your hands and knees.”
I hesitated, pouting.
“Hands and knees, now.”
I had barely gotten into position when a hard smack rang out, heat blossoming on my ass where he had struck. He started a pattern, moving down one cheek and then the other. When both cheeks had been covered he gave one last slap at the crease of my ass between both, forcing me to clench around the plug and moan.
“Why are you being spanked?”
“Because I was being bratty, Sir.”
“Does Sir like a bratty sub?”
“No Sir.”
“No he does not.”
He repeated the pattern, over and over, until my ass was satisfactorily red and stinging. He spread my legs, ghosted his fingers across my cunt and the flared base of the plug. And then he was inside me.
The curve of his cock hit my gspot just right, and the press of his hips pushed the plug in more firmly. I couldn’t trace the end of one moan or the start of another, I was so lost in the pleasure of him. And when I thought I couldn’t feel any better, he turned on my wand vibe and placed it right under my clit, grinding me into it and making me scream. The tighter my pussy clenched around him the harder he slammed into me, determined to fill me. And a moment later, he did, shouting my name in elation as his cum coated the inside of my cunt. The weight of his final thrust held me against the vibe and I was shrieking and twitching, still orgasming around his spent cock.
“Red, red, RED!” I shouted the safe word, unable to stand any more pleasure. He turned off the vibe and pulled out slowly, kissing my back and my hips and ass and thighs.
Jelly-legged, I struggled to lay down, shaking with aftershocks. The room went dark and his warm arms surrounded me, his body pressing tight to mine as he pulled the blankets around us.
It was the perfect night.

Last Fuck of 2016 Wasn’t What I Expected – MILF

Last night I decided I didn’t want to stay home to watch the ball drop like usual. I was feeling a bit horny and while I didn’t expect anything, being at home alone wasn’t increasing my chances of getting laid.
I headed to a bar down the road where they were hosting a New Year’s Bash. I knew there would be some drunk girls there and thought that I’d have a decent chance being 5′-11″, ~200 lbs, blue eyes and nicely cut brown hair. I like to think I am fairly attractive at least.
I get to the bar and take a seat ordering a shot of Jack. Boring, I know. I down it and order another on the rocks to sip on while I peruse. There are tons of gorgeous women there from blondes to red heads and brunettes.
I talk to a few of them and even get a few numbers. All in all, the evening was going pretty well. I ordered more drinks and before long, I really had to pee (and was feeling really buzzed).
I excused myself from my present company, a cute blonde girl who I don’t think was 21 and her brunette friend who was buying her drinks, and headed to the restroom.
The only open place to take a leak was a stall on the end so I went in and locked the door behind me. I unzipped my jeans, whipped out my cock and began to relieve myself with a sigh of relief.
As I am finishing up, I hear a light tap on the stall wall beside me. I turn to look and discover a rather hard, ~8″ long, thinish, white cock poking through a hole I hadn’t noticed earlier.
If you’re read my other stories, you know I am no stranger to cock and like it as much as the next guy who has tried it. I shake the remaining piss from my cock and zip up. I reach out to grasp his cock. I mean, clearly he needs a hand.
I begin to slowly stroke him eliciting a muffled moan. That sets me off. I drop to my knees and take him into my mouth. This is hot. I’ve never been in a gloryhole before (I of course never stayed in this bar long enough to have to pee either).
I begin to bob on his cock slowly trying to be quiet. There are a lot of people coming in and out of the bathroom, but it’s hard to suck a cock and not slurp some. I come up with another idea. I stand up bent over, pull out my wallet, and undo my pants dropping them, all the while sucking this strangers cock.
While I suck, I pull free a condom from my wallet and open it. I stop sucking to slide it on him and back up to his cock letting him enter me. Thankfully he was thin or this would have been much more difficult. I back up to the stall wall and clench my ass. He begins to thrust into me, pumping hard and fast as one can in a stall. In short order he taps the wall and I clench my ass in reply. He thrusts a few more times cumming hard (with more of a grunt than I would have wanted trying not to be caught).
When he finishes, he pulls out, flushes the condom and zips up leaving. I pant as I ALMOST came. I decide to finish myself off and start to stroke. No sooner have I started than the door next to me closes again and another cock comes through.
I don’t even hesitate. This one is smaller, 5″ but thicker and tan. I suck like a champ for a minute before I start to, once again, get too noisy. I pull out another condom and put it on this nice specimen of a cock.
I back up to him and in less than 3 thrusts, he grunts cumming hard. I smile to myself for a second having done such a good job that he came so fast. As he finishes, he too pulls free, flushes the condom and leaves.
I decide to wait. Maybe someone else will come in. I’m really rather turned on about being a slut tonight and no longer care to hook up with a girl. I want to make more cocks cum.
In short order, a body is in the stall and I slide a finger through the hole as I hear him piss. I am rewarded with a cock tip touching my finger. I withdraw it and the cock follows. I smile to myself. This one is a gorgeous black cock. Thick and long, maybe 8 or 9″?
I suck hungrily on it while I free a condom from my wallet (I like to be prepared when I leave the house with the intention of getting laid). I unroll it onto him and bend over for him to use my ass.
He doesn’t disappoint. He slides in easily enough after I haven been stretched by the other two, but he is still big and feels good. He starts thrusting and I know instantly I won’t last. My ass clenches as my orgasm approaches (damn I love prostate stimulation!). He speeds up liking the tightness and I scream out pushed over the edge. I spray all over the floor in front of me, cumming hard, KNOWING everyone has heard me and not caring. He doesn’t seem to either as he keeps thrusting, harder now.
In short order, I hear him grunt as I am coming down from my orgasm. He is filling the condom so well I can feel the jets even through the rubber. I moan as he does.
As he finishes, he pulls out and flushes the condom like the rest. I stand there legs shaking unable to move or stand up.
I should have moved. Another cock is through the hole and in me before I can do anything about it. I try to move away but my legs are shaking and his cock feels so good, I don’t want to move. Instead, I thrust back onto him, the stall wall shaking with the force. We keep up this fucking for a good few minutes. I don’t know what his cock looks like, but damn it feels good. It’s thick and veiny. I can feel the ribs of it. I moan as another orgasm approaches my cock.
He grunts and then knocks on the stall. I squeeze my ass. Maybe we can cum together. He speeds up, thrusting deep into me, fast. I scream out again with my second orgasm of the evening, spraying the floor.
As I cum, he cums, HARD. I then realize he didn’t have on a condom. I feel each and every jet of cum spraying my insides. My first creampie is from a stranger. He keeps thrusting and shooting, my body shakes as I cum (and from a little bit of fear).
Soon, he too is done and I am left there shaking. I move to the toilet and sit letting his load drip into the toilet from my used and stretched ass. I feel both amazing, and afraid. I am on the verge of tears and am trying to fight them back while at the same time trying not to stoke and cum again.
A second later, a paper towel slides under the stall. Sloppily written on it was a note: “I’m sorry about that. I meant to pull out, but you felt so good. I’ll be waiting at the bar. I’m wearing a green shirt and will be looking at the bathroom exit. I hope you come talk to me. If you don’t, know that I am clean and you have nothing to worry about from me.”
I shook and smiled and cried and then jacked off cumming for the third time all over the floor. I got dressed not even bothering to clean up the condom wrappers or cum. I stuffed some toilet paper into my pants under my ass to catch the cum that hadn’t escaped and then left the stall, washed my hands and headed to the bar.
Waiting for me was a rather cute young man wearing green, looking right at me. He was blonde and looked to be in good shape. His hair was cut short and he had on a pair of glasses. Not the type I would think would be at a bar, much less would fuck a guy in a gloryhole.
I walked up to him. “Hi…” I all but whispered.
He smiled. “Would you like a drink?”
I nodded, and he ordered me a Jack and Coke. I sipped on it and began to relax again. We talked for a good while, and brought in the new year together, though without the traditional kissing or any sex.
We did exchange numbers and are planning on meeting up again sometime soon. I have already texted him this morning and he texted back.
While the end of 2016 was a real list of experiences, and an emotional roller coaster, I have very high hopes for 2017 now.

How I had the best sex of my life, and the moral implications of it. Part 2 – MILF

First of all, whoa! I never imagined my long-winded story would attract as much attention as it did. Thank you to all of you who left words of support and feedback. I performed a mental fist pump each time a Redditor said I helped him/her get off. Part 2 picks up where I left off, and wraps up my adventures with Mindy. Go to the break for the sex you’re all here for.

So there we were, laying on the air mattress naked. I undoubtedly experienced the best sex of my life, all the evidence of that culminating in our combined fluids on my slick penis and damp pubic hair. Mindy was still panting, my shirt underneath her butt catching those fluids that dripped out. When the guilt slammed into me, I got up slowly and wobbly, and headed towards the bathroom.

I stepped into the shower and washed myself off, paying particular attention at lathering and rinsing my dick off. I used to love falling asleep after sex with my ex-gf, and my dick would be glistening and sticky as an arousing reminder of what happened. Now, all I could think about was how I had completely unprotected sex with a girl whose sexual health I had no clue, and the potentially catastrophic consequences of getting her pregnant or passing on an STD to my fiancée.

Mindy was still laying on the air mattress when I returned, and she said with a sleepy smile, “My head is still whirling from the wine and the sex.” “Let’s go to bed,” I offered to her.

“Are you ok?” Mindy asked as we walked to the bedroom. “Yeah, I’m fine,” I replied probably not too convincingly. As we laid down, I timidly asked her, “I’ll get you the morning after pill tomorrow, and I know we should have talked about this earlier, but are you clean?”

“Yes,” she whispered, sounding hurt. “I’m clean, and I get tested regularly through work.” At the time she worked at a hospital, another element of her endearing, caring personality. A huge weight lifted off my chest, yet I still had trouble falling asleep. After some time, she got up, and told me, “I should probably go.”

I implored her to stay, as it was getting late and I didn’t think she was 100% sober yet, but she insisted. Before she left, she told me (paraphrased since I can’t remember precisely), “Taketomygrave, you’re an amazing guy. I really hope I didn’t ruin our friendship by coming here tonight. If nothing else happens, I hope you’ll accept this as my gift for your bachelor party. I really want nothing but the best for you.” We hugged and she went home. I barely slept all night.

The next morning, I get a text from her saying something along the same lines: she had a great time, she hoped we can still be friends, I’m a great guy and she doesn’t want to hurt me, etc. And that she took the morning after pill, so we didn’t have to worry about that. I responded that I really wish she had stayed, reiterated that I had an amazing time too, and thanked her for taking care of the morning after pill.

Around midday, I get another text from Mindy, “I still can’t believe how good last night was. I’m really really sore … I’ve never done a one night stand before yet I just couldn’t control myself.”

“I’ve never had a one night stand either. Last night was incredible for me too. I still can’t get over how you let me cum inside you when we both knew you were unprotected. I know … I just wanted you so bad I couldn’t stop either.”

“I just trusted you and felt safe with you. Though I was a little hurt afterwards that you asked if I was clean.”

“I’m sorry, we should have talked about that before the clothes started flying off.”

“It’s ok. I just want to make sure you’re ok with what happened. Your cum is still dripping out of me, and I love feeling it inside me.”

Well, that gave me an instant boner. Pretty sure my face was flushed too, and I hastily looked around to see if any of my coworkers suspected the erotic texts that were on my phone.

I replied back, “God that’s hot. I loved cumming inside you. I’ve never even gone bareback with my fiancée.”

“Really?? Never? But you’re so handsome and passionate and such a good lover. All of my girlfriends say they give their bfs that treat once in a while.”

“Never. That’s just one of the many reasons it was so special last night.”

“I asked a doctor friend of mine about the morning after pill today to make sure I’m taking it correctly and at the right time. She told me there could be side effects, and my period would start.”

“I actually feel pretty bad that you have to take that. I had a friend who worked at the campus clinic in college, and she said Plan B would make the girls who took it feel very sick.”

“It’s ok. It was worth it with you. I just hope Lanh doesn’t suspect anything, since our periods happen at the same time. I hope she doesn’t ask why mine’s starting 2 weeks early.”

“Wait … 2 weeks? That means you are really fertile right now.”

“Yes, if I didn’t take that pill, you would have gotten me pregnant.”

“Wow … we really took a huge risk then. That makes it even hotter for me somehow.”

“I had to write all of this down when I got home, it still feels like a dream.” She proceeded to reminisce from her point of view, starting from the basketball game date: how cute I looked, how some of the things I said to her were particularly endearing to her, and how she loved feeling pressed against me on the packed train ride home. Then on to dinner, how happy she was to cook for me and to see me devour her creations. Then to the sex: how aroused she became from the passion of my kisses, how she exploded when I first touched her, how good the orgasm was from my tongue and fingers, and how she came again when she felt me cumming inside of her.

Needless to say, I was pretty fucking distracted the whole day at work, and the texting continued all day Friday and Saturday. At one point, I teased her that I was eating dinner alone, and she playfully chastised me for being so silly when she would have kept me company for dinner instead of hanging out with Lanh.

Fast forward to Saturday night, I had been home all night, and made plans to see some friends on Sunday. Mindy and I texted throughout the day, mostly about what she and Lanh were up to, including a few pictures of them getting ready in various states of undress for their girls’ night dinner. Then about 1AM, she told me that Lanh was ditching her to go “see a guy who’s leaving town” and asked if she could come over. I thought that it was awfully late, and started worrying that she and Lanh were plotting this together, but my other head overruled me and I invited her over.

She hopped into an Uber and got to my apartment. I waited for her downstairs, and saw her come out of the car. This time, she was wearing a more modest teal sundress that came down to her knees and showed just a hint of cleavage in a classy way. As we went up to my unit together, she kept on smiling and saying “this is so crazy.” I offered her some water, and we agreed to head to bed. She went to the bathroom to change, and came out in a t-shirt that just covered her butt, and I saw the skimpiest red thong underneath as she climbed into my bed.

I turned onto my side to face her, and she eagerly sought to be in my embrace. I tilted her chin up and kissed her full luscious lips that had a fresh application of lip gloss. We made out slowly, enjoying the feeling of each other’s lips, and when her tongue started to dart into my mouth, the intensity picked up. I caressed her cheek and her arms, marveling again at the smoothness of her skin, as she started to dig her nails into my back. I reached across her arms to get a squeeze of her magnificently ripe breasts, but she pulled me closer to cut off the angle of attack.

“Just keep kissing me,” she breathily moaned, and we continued the passionate kissing. Being a handsy guy, my hands never stopped roaming across her back, her arms, her sides, and her legs, wherever I could reach. After several minutes of making out, I felt horny and mischievous enough to slide my hand between our bodies and slipped under her thong to touch her pussy. I managed to feel her wetness briefly before she pulled away giggling, playfully slapping my hand. “This stays on tonight!”

Sensing my disappointment, she started to caress me lower, from my back and pecs to my abdomen to my crotch. The area between my dick and belly button is somewhat of an erogenous zone for me, so her hand there was turning me on immensely. She grasped my penis and squeezed it gently, moaning with approval at how hard I was for her. She pushed me onto my back, and I helped her remove my undies. Sweeping her hair behind her neck in one graceful motion, she leaned down and took the tip of my dick into her mouth.

“Ohhhh…” That was heavenly. She did the same thing as the previous night, swirling her tongue around my head and across my opening, and gently bobbing her head on about the top 3 inches of my shaft. She was crouched diagonally with her feet pointed toward my head but away from my body. From my supine position, I could only reach her back, legs, and her little red thong. I grabbed the strings of her thong and held on while she serviced me dutifully with her mouth. Again, she had me tingling all over but not close to orgasm, and I groaned out, “I need you… I need to be inside you.”

She paused for a second, and then I saw her start to shimmy out of her thong with one hand while keeping me in her mouth. She dropped her thong by the side of the bed and spun around to straddle my thighs. I sat up and kissed her, telling her how wonderful she made me feel with her mouth, and pushed her t-shirt up over her body. She eagerly helped me by raising her arms up, and she scooted forward on top of my dick.

She rocked back and forth on the underside of my penis for a few seconds, while she must have been relishing the stimulation against her clit and lips. I certainly enjoyed feeling my dick get slipperier as she covered me in her juices, and laid back down. We watched each other for a few seconds, her eyes half-closed as she used me for her pleasure, and I soaked in her stunningly beautiful figure. Without another word, she lifted off me just enough to pull my dick to alignment and sank back down, completely engulfing my penis in her luxuriously velvety walls again.

I held her hips as she rocked and grinded on me back and forth to start. There was a surprising amount of stimulation from this even though not a single inch of my dick left her pussy. I stroked her hipbones and sexy waist with my thumbs, and pushed both hands up to cup her breasts. She held my hands against her boobs, squeezing them together like what a push-up bra would do, and leaned over to shove a fascinatingly erect nipple into my mouth. I obliged her, and I licked, sucked, swirled my tongue, and grazed my teeth against her nipple like my life depended on it. Right as I released it to take a breath, she switched and fed me her other nipple, and I gave it just as much attention as its twin.

She stabilized herself on my chest and began riding me. The way she moved was incredible. Her hips and torso moved like a wave, and on each downstroke, the crown of my penis rubbed firmly against her pubic bone and front vaginal wall, which felt mind-blowing. [I tried to find this NSFW video on reddit where the girl moved and rode exactly how Mindy did it, but had no luck.] I had an unsettling thought of where she could possibly have learned to ride like this, but the sensations of her bare pussy quickly drowned them out. She was pushing me to the finish line, and fast.

“Mindy … You’re gonna make me cum if you keep riding me like that!” I warned her, giving her a chance to hop off if she didn’t want to deal with my sperm in her again. She responded by riding me even faster and gave this adorably long, sexy gasp, “Ohhhh!” Another thing I loved about her was the noises she made during sex. They were always these quiet gasps and pants, not the shrill squeaks you hear in pornos of Asian girls that really annoy me.

Hearing her gasp like that did me in. [She would later tell me that she came when I told her that her riding was making her cum, even though I couldn’t feel any vaginal spasms like the other girls I’ve been with.] I grabbed her hips again, and thrusted upwards as far as I could shove myself in her pussy, and launched my cum into her. She slowed down as I continued to throb inside her, no doubt still releasing small drops of life-giving fluid into her pussy. She slumped down on my chest, and we just lay there resting together for a couple of minutes until I softened and popped out of her. She rolled over, and I offered her my shirt without asking. She giggled at my chivalrous act that I learned from our previous session, and without any actual cleanup (which was hot), we held each other to sleep.

In the morning, I woke up first and found us in the spooning position. Seeing this beautiful girl in my arms in daylight had me aroused again in no time, given the headstart from my morning wood. I nibbled on her neck and ear while caressing her tummy and those smooth toned legs. She started to stir, and when she realized what was happening, she groaned audibly and pushed her butt back to grind against my rock hard penis.

I didn’t waste much time at all, gently signaling for her to lift her top leg up, and I reached down to make sure she was wet. She was moist and getting wetter by the second. I inserted an exploratory finger in her and determined she was indeed aroused. I reached between her legs and guided my penis to her entrance, and curled my hips to penetrate her.

Mmmm, that first feeling of unprotected penetration is unmatched. I started thrusting into her and she reciprocated by pushing back into me. After a few minutes though, my hip and leg were starting to chafe on the bedsheet, so I pulled her leg up and around, and plunged back into her in missionary. She wrapped her arms around me and started to really rake my back. I could feel her nails scratching along my shoulder blades and down to my lower back.

This was the first time I tried to hammer her as fast as I could, and of course you could guess by now that I couldn’t last long inside her like that. I pushed up in a plank position, and roared as I came in her again. I saw her turn her head, and I realized she must have gotten a whiff of my putrid morning breath, so I dropped down next to her ear.

“Sorry about my breath,” I whispered.

“It’s ok. Keep cumming inside me. Oh my god! Oh my god!” she urged me on, and the rest of my orgasm continued in diminishing spasms. Before I softened, I wanted to admire her, so I pulled out my dick from her now very well-fucked pussy, and she groaned as the head of my cock slid past her lips. “Uhhhnnn!”

I thought I had hurt her at first, but she later told me she had a mini orgasm as she felt me pull out all the way while still hard. None of my semen was leaking out of her, but I could definitely see some resting in her tunnel. I felt so proud and masculine at that moment, in a way that I hadn’t felt in a long time, upon seeing her filled with my sperm.

The good feelings dissipated though as soon as the orgasmic high wore off, and the guilt took over again. I got dressed and asked Mindy to get dressed in an effort to get her to leave before I had to meet up with my friends. I had a rule when I was dating to always make breakfast or take a girl out to brunch if she stayed overnight, regardless of whether we had sex or not. [Guys, from my limited experience, the chances you get laid the next time by doing this is much, much higher!] I felt shitty for breaking that rule, but hey, I was feeling pretty shitty overall.

I managed to not see Mindy in person for about a week, with the exception of a Super Bowl party at Lanh’s place. There was definitely a lot of eyeing each other that went on at the party, and at one point she did whisper in my ear, “Mr. Taketomygrave, the things I want to do to you … My period is ending, but my boobs still feel tender and bloated” amidst loud conversations. Her boobs did seem a bit bigger than normal. And when I hugged her and Lanh goodbye, she firmly raked my back with her nails again as an allusion to our previous fuck.

The final time I was with Mindy, she and Lanh came to my building the next day, where another friend of Lanh’s lived. I was chatting and socializing with some neighbors on the rooftop when I got a text from Mindy saying that she was in the building for the other friend’s party. She didn’t have much time to just disappear from the party, but she wanted to say hello.

Thinking it’d be pretty harmless chatting, I took the stairs down two floors and met her on her friend’s floor. I surprised her by coming out of the fire door, but she smiled and walked over, and ushered me back into the stairwell.

“I can’t be gone for too long, or else Lanh will worry and ask me a bunch of questions. I told her my mother was calling.” With that, she grabbed me and started making out with me. I was a little stunned, but the soothing smell of her shampoo and perfume made me remember all of our previous sessions, and I started kissing her back in no time.

“I just want to kiss you again,” she moaned into my lips. And we kissed each other furiously for several minutes in the stairwell, which was all the more exciting that somebody could easily walk in on us if they took the stairs.

“I’m not wearing panties again right now,” she admitted in a seductive whisper. “Really??” I asked her back. “I took them off before coming out here. They were almost ruined from thinking about you.”

I tried to reach under her skirt to confirm the veracity of her statement, but she slapped my hand away with a naughty grin. “I want you to cum in my mouth this time.”

She dropped to her knees and unzipped my pants. She worked my penis with vigor for several minutes, all while giving one of those sloppy, drool-filled blowjobs. I loved watching my dick go in and out of her mouth and felt close to cumming, but her jaw must have gotten tired, so she looked up and asked me, “Do you want my pussy?”

I closed my eyes, thinking about how to refuse her this time, but when she asked me again, I just dumbly nodded, and sat down on the bottommost step. She flipped her skirt up (no panties confirmed) and sat down on me. She had a couple of days’ worth of stubble on her pubic area, which I noticed and stroked through it as she impaled herself on me.

I am ashamed to admit that I was literally a two-pump chump that time. A combination of the hotness of that stairwell rendezvous, how close I was already, and her magical pussy got me to blow my load in her after two strokes. She got off and stepped back. One glob of semen dropped on the stair step and one glob of semen fell on my pants that were around my ankles.

We put ourselves back together again as best as we could, and she gave me a kiss before dashing back to her friend’s party. I took the stairs down to my floor, hoping not to run into anybody who might see the gigantic cum stain on my pants.

EPILOGUE:

I have only seen Mindy a couple of times since then, and always with Lanh and a group of friends. Each time, she avoided me like the plague. I actually texted her to wish her a Merry Christmas last week, and she responded saying she doesn’t wish to text privately with me anymore. She said she felt extremely bad for compromising her Catholic morals (I wasn’t aware she was Catholic), and asked God for forgiveness everyday, and wished me the best. I think she also blocked me on Facebook.

Sorry there is no fairy tale ending … I think it’s for the best that this story ends. Thanks for reading, and Happy New Year!

An afternoon of many firsts – MILF

This all happened four days ago. After a very hectic morning, I[20F] arrive at his[33M] apartment at around 2:30 in the afternoon. I text him that I’ve arrived and then just stand at the bottom of his stairs for a few seconds. I’m a little nervous. I’ve never done anything like this before. But my ride has already left, so there’s no turning back now. But I wouldn’t have wanted to anyway. I was determined to be with this guy.
I walk up the stairs and he opens the door for me. This is a very familiar experience, as I’ve been to his place a few times before. I’m never sure if he’s just standing at the door waiting to open it, or if he just happens to open it right when I get there. I’ll probably never know. He lets me in and the tension increases. We exchange brief greetings and he takes my coat so I can remove my shoes. Then he leads me to his bedroom. Also a familiar experience, as he has roommates, so we usually hang out in his room. But his roommates are gone this week. We have the place to ourselves.
I start to express my frustrations with the morning I’ve been having, so he offers me a chair so I can sit and just breathe for a second. Then he comes over to me and starts giving me “head scratches”. We have a Master/Kitten relationship, so this is just something that he does to me. I find it to be cute and endearing, so I giggle and lean into it. But I know that this is him trying to transition into what I really came here for, so I stop him before he can continue. I tell him that I want to go change, to make myself more comfortable. As the clothes that I’m already wearing are very loose-fitting, he gives me a confused look and says, “A baggy sweater is uncomfortable?” It’s true that I was already pretty comfortable. He got me there. But those weren’t the clothes that I wanted to do this in.
So I take off to his bathroom, change of clothes in hand. This wasn’t plan A. I would have just loved to strip right in front of him and forget about clothes altogether. But mother nature can be a bitch sometimes, and I happened to be on my period this week. He knew, he was bummed. I was bummed. But that wasn’t going to keep us from having some fun. I remove my baggy pants and sweater in exchange for a cute pair of shorts and a form fitting shirt. I even remove my bra, just to get that step out of the way. The shorts were important because this was the first time I was really going to let him touch my skin, and I wanted to give him a very easy time in doing so.
I come back into the room and put my clothes with my bag. He gets up from his desk, comes over to me, and starts snuggle-hugging me. I love his snuggle hugs. He’s a good head taller than me, so they’re very comfy and soothing. While still hugging me, he spins me around and lays me onto his bed with himself on top of me, smothering me. He knows that I like being smothered and he has done this before. He asks me how I’m doing. I just giggle in response. I love how forward this man is. I love how he wants to know what I’m thinking.
He has a cat, and while we are laying there, his cat comes in the room and jumps up onto his back. I’m petting the cat from under him and laughing. I joke that his cat is a terrible wing man, to which he replies, “Yeah, he’s a dick.” But his cat was actually being a great wing man, because the interruption just calmed me down and eased the mood. But after awhile, the cat has to be sent out of the room and the door shut so that we can be alone.
After a few more minutes of sweet smothering, we both want to progress this somehow. I am unsure of what to do. I want to kiss him so badly. But I’m so new to all of this. I had made out with a guy before, but in that situation, he was very much the sub with me taking the lead. Now I am the sub. I prefer being the sub. And I want Master to take the lead. But I would have kissed him first had he taken any longer.
He eventually leans down and kisses me on the forehead. It’s so unexpected, and I start blushing immediately. It’s the cutest thing that he has ever done to me. He asks me what I think of it. “That was so cute,” I respond. He leans down further and plants a quick kiss on my lips. “How about that?” he asks. I respond by simply pressing my lips back against his. It’s awkward, but first kisses always are. I make little mental notes of how he feels, how he tastes, how he moves, so that I can think about them later when we’re apart. I think about kissing him so often, and now I’ll have true memories to fantasize about later.
I’m just starting to get used to his lips when he suddenly pulls them away. “No! More kisses! More kisses, please!” I plead. “More kisses… what?” He looks at me expectantly. “More kisses… more kisses…?” I know what he wants me to say, but at the same time I don’t want to get it wrong. “Come on, Kitten. More kisses…?” He persists. “…More kisses…Master?” The word barely leaves my lips before he’s pressing his against mine again. I guess that was the right answer.
He rolls off of me and repositions us in a sideways embrace. We continue kissing as he runs his hands up and down my body. I don’t know which to focus on: his wonderful lips or his wonderful hands. He’s treating my body quite delicately, but every once in awhile, he grabs my flesh and squeezes. I wish he would just do this everywhere. It’s such a pleasurable sensation. He puts his hand up underneath my shirt and starts touching my breasts. It’s exciting and it makes me feel so shy at the same time. He’s the first person to ever touch me here. He glides his hands over my chest and starts pinching my nipples. This takes me a bit off guard as it is a really intense sensation. A bit too intense. Almost painful. I wonder why he wants to do this to me. I wonder if he has done it to past partners.
He repositions again so that he is on top of me but shifted down my body. He lifts my shirt and fully exposes my breasts. My heart is racing and I’m feeling really shy as he brings his lips to my nipples. I can feel his rough stubble against my chest. It tickles. I like looking down and seeing the top of his head as he does things to me. It makes me feel all warm and affectionate to this man on top of me. He sits up, looks me in the face, and pulls off his shirt. It’s a really great moment. I’m looking at his handsome, hairy chest and just thinking to myself, “My God, this man is sexy.” I probably should have said that out loud. I feel so giddy and excited to be getting it on with this mature hunk of he-man. He presses our exposed chests together and my mind starts short circuiting as we start kissing again. This lasts very briefly, as he soon rolls off of me completely so that he’s laying on his back.
He says something to me. I can’t remember what he said now, because all that translated in my head at the time was that I was going to get to see his dick. Whatever he asked me, I respond positively and he begins removing his pants. But I quickly stop him because I want to do it. I want to get to unleash the beast. So I unzip his pants and start trying to pull them off of him. He has to help me, because I’ve never done this before, and I’m not doing it very well. But the whole thing just makes me really happy. I finally get his pants off and I toss them onto the floor. The underwear comes off a little easier because now I understand how the mechanics of this situation have to work. I secretly compliment his good taste in boxers. Again, I probably should have said this out loud. Underwear off, I look back at him and ask if he wants his socks removed. “Either way,” he responds. So I take them off. You can’t be naked with just socks on. That’s just not allowed.
Now that he’s fully naked, I come back up and sit next to his waist and really take in the appearance of his cock. I’ve seen it before in pictures and videos that he’s sent me. But in person, it’s a whole different story. I’ve never seen a penis in person before. But I love the way his looks. I always have. I’ve seen my fair share of dicks across the internet. But his just has a certain appeal for me. There is just something really pleasing about his size and head to girth ratio. And now, here I have this sexy, naked man in front of me asking if I want to touch it.
Not wanting him to feel alone in his nakedness, I pull my shirt off and toss it aside with his clothes. I am just beside myself with excitement. Oh boy, did I want to touch his member. I reach out my hand, but I’m just so nervous. I don’t know how to touch a cock. I don’t know where to touch a cock. Finally, I have to ask him to place my hand on his cock. This is a tactic that I’ve had to use before when my mind really wants to do something but my body is having trouble executing it. He takes my hand and puts it on his shaft near the base, and I start fucking losing my shit on the inside. I start moving my hand up and down him a bit. His member is warm and hard and ridged, it’s a little different than what I expected. But I really don’t know what I expected.
I’m really unsure of what to do to him, so he asks if I want to put my mouth on it. I don’t remember if I even said yes. I just jump at the suggestion. I may not know how to use my hands, but I know how to use my mouth. He just looks so delicious and he’s dripping precum. I don’t even need to think twice about it. I dive down and instinctively put his whole tip in my mouth, leading it in tongue first. And that taste. Holy fuck, that taste. I’m a vegetarian, but he just tasted like meat. Like warm, fleshy, erotic meat. It flipped a carnal switch on inside my head. I felt like such a tiger, and I just wanted to devour this man and his tasty member.
I lick all over his tip and up and down his shaft. It’s not that he necessarily tastes good. He actually tastes quite salty. But I’m not hungry for food, I’m hungry for cock. His cock. This is his cock, and I love it. I kiss it, take it in and out of my mouth, drag my lips down it and kiss the base. He tells me that this doesn’t seem like my first time. Those words fall like sweet music on my ears. I suck on his tip, and take him in as much as I can at different intervals. I’m surprised at how difficult this actually is. I’m surprised by how fully he fills my mouth.
But my favorite thing to do is just lick him like an ice cream cone, and I do ample amounts of this until he weaves his hands through my hair and pulls me up to his face to kiss me again. It’s a really hot move on his part, and I’m taken aback once again by how sexy this man really is. I rest on his chest kissing him, until I have to reach up and tap on his hands in my hair and tell him that he’s pulling too tight. He apologizes and let’s go of my hair. Again, really hot. Sorry becomes such an intimate word when you’re in a completely vulnerable situation with someone like that. I was already sold on this man from the beginning, but with each successive minute he continues to sweeten the deal further.
He pushes me off of him a bit and says that he has an idea. He gets up off the bed and walks over to his desk chair. I get a nice look at his ass and am reminded that just as much as this man is sexy, he’s also really cute. He sits down on the chair, spreads his legs, and looks at me expectantly. I love the way he looks in this position, with his whole package out for my full viewing pleasure. And it is pleasurable to look at. I’ve lost track of how many times he’s blown me away with his sexiness by now.
I crawl off the bed and get on my knees in front of him. I feel so turned on to be in this position of submission for him. I look up at him for reassurance, and then go back to work on his member. It’s much easier accessing him in this position, with his dick level with my head. I put one hand under his balls, which I would just love to play with more, but have no idea how to. I hold his member with my other hand and take him back into my mouth. I play with him a bit more, licking him and doing the things I like, until he places a hand on the back of my head.
I know what he wants to do, and I’m glad he wants to try it. I’m glad that he wants to take control of it. I love it when he takes control. But this is not a beginner move, and I discover that very quickly as he starts shoving my mouth onto his cock, making me face fuck him. Or trying to at least. We get about two strokes in before I start gagging. He lets up on my head so I can back off and catch my breath. I apologize for my inability, and he assures me that there is nothing to apologize over. We try it again, and once again only get about two strokes in before I can’t stifle my gag reflex and start choking on him. He lets up. I apologize again.
I look up at him with watery eyes and tell him that he’s just a lot to take in. He reminds me that he’s only average sized. I don’t know why he continues to remind me of this. I love his size. I wonder if seeing me all teary eyed is turning him off, so I start wiping my eyes. He grabs my hand and holds up two of my fingers against his cock to show me the size difference between what I can fit inside me now and what he’s packing. I have not considered this yet, and it’s blowing my mind. I remind him that I’ve really only been able to successfully fit one finger inside me since I began experimenting with it a couple weeks ago. I hold a single finger up to his dick, which is easily six times the width of my finger. I’m getting excited. Someday I’m going to get the pleasure and challenge of trying to take this monster inside me. I can’t wait for the day when I’ll get to try.
I go back to sucking him off. I really can’t help myself. I love doing this. I love having his cock in my mouth. I hope that he’s enjoying this. He stops me to show me how to do something. “Yes, Master. Please teach me. Show you’re Kitten how to pleasure your cock.” He puts my hand on his shaft and tells me to hold firmer. Firmer. Firmer. I’m already learning a lot about how rough I can really be with him. Then he tells me to suck his cock in sync with jacking him off. I immediately understand what he means and go right to it. I’m glad he’s showing me what to do. I want this to be amazing for him.
His body jerks a little as I start going at it, and I can tell that he is pleasurably surprised with my performance. This is a good sign. He tells me that I am a natural at this. It feels very natural to be doing this. I’m maintaining a good grip and forcing his dick against my tongue as I’m taking it in and out of my mouth. He starts precuming again, and every time a new wave of it hits my tongue, it just increases my crazy, carnal desires for him. I want him. I’m currently getting him, but I still want him. It’s like I can never get enough of him.
I continue this technique, but can’t breathe very well as I do it. So I hold a pace, then let up to breathe, then pick up the pace again. I hope that this is okay for him. He reaches down and starts pinching my nipples again. I’m glad that he wants to touch me while I do this to him. I take it as a good sign. I keep trying to listen for his breathing, but my face is so hot that I can’t hear anything anyway. I want to look up at his face, but that is impossible to do and keep up this rhythm at the same time. The physical impossibilities of reality can be so frustrating sometimes.
Pretty soon, he touches me to get me to slow down, and asks where Kitten would like Master to cum. My brain is so overloaded with sensations right now that I don’t even register what he means. He asks again more specifically. “Would Kitten like Master to cum in her mouth, on her face, on her chest?” I want him to cum in my mouth, but I’m so nervous to ask for it. I’m afraid that I’m not ready for it. But if he wants to, then I want him to. I start kissing his dick tenderly as I consider how I should respond. “Where would Master like to cum?”
“Master would like to cum on Kitten’s face.” He pushes me more away from him now and gets ready. I like this choice, but I’m just so anxious because I don’t know what to expect and I’m afraid of how I might react. I don’t want to let him down. I ask if it would be alright if I close my eyes. I think he can tell that I’m unsure about this, because he asks if I would rather that he cum on my chest. I’m so grateful that he is so thoughtful, even at this moment. It makes me so happy to be experiencing this with someone who is so considerate of their partner.
As it would make me more comfortable, I take up Master’s offer to cum on my chest instead. “Then Kitten will have to get up and lay on the bed.” I scurry up right away and lay back down on the bed. Anything for Master. He climbs on top of me. This is so exciting. I’m glad we decided to do it this way. He begins jerking himself off. I want to watch him do it, but his face is commanding my full attention. Commanding it. I can’t look away from him. He begins describing these wonderfully naughty things to me. How he would rather be inside me right now, filling me with his cum. I’m burning so badly for him as I look into his eyes and listen to these wonderful things. I’m so overwhelmed to be hearing them in person for once. It still hasn’t really hit me that we’re actually doing this right now. It all seems like such a wonderful dream.
Then I feel his cum start shooting onto me. It’s so forceful, and wet, and warm. I’ve dreamed so much about him and his cum, and now he’s shooting it all over me and I couldn’t be happier about it. I lose focus on anything else that’s happening except the sensation of his cum landing all over me. When I sort of come back to reality, I start rubbing his cum into me and looking at him while I lick it off of my hands. He grins at me. It’s a very fun moment.
But the next thing I know, his jumping off of me and getting dressed again. I’m sad that he wants to put his clothes on so soon. I wasn’t done admiring his body yet. He throws me a towel to wipe myself off with. It is at this point that I realize just how much he came on me. I’m so excited about it. From start to finish, this man has just exceeded all of my expectations. He comes over to me and takes the towel from me. “You missed a spot.” He says as he starts wiping cum off of my neck. It’s such a small gesture, but I just can’t help but melt from it. It’s so sweet, and cute, and sexy. He’s so sweet, and cute, and sexy.
He brings me my shirt and starts telling me how it’s best to just laugh after these things. I don’t know what he’s talking about. I don’t know what I’m supposed to be laughing at. I’ve just had one of the best experiences of my life. I’m just so happy and pleased about it that I start laughing anyway. “That’s the spirit.” He tells me. He asks if I want to cuddle. Of course I want to cuddle. So he puts on a video, and we lay there together with our clothes on again. But I can’t stop thinking about everything that we had just done while our clothes were off.