The night I met Michelle was a night I was wholly unprepared for, it was a fairly lowkey party at a friend’s house where our mutual friend Todd introduced us. She was short with chestnut brown hair just past her shoulders, low cut black top over an obvious c-cup, and tight jeans over a beautifully shaped ass. She was pouring shots of Jameson and pushed one into my hand after we exchanged pleasantries. We talked and drank for a while and after putting down a generous amount or whiskey, she turned to me with a sultry smile and said “I’m gonna tell you, I’m curious, a nice guy like you must have a great cock and that’s all I’ve been thinking about for the last ten minutes.” I laughed, caught a little off guard by her no bullshit attitude, and quickly took mental inventory of the other partygoers. Everyone seemed to be either in the kitchen or living room, I finished my drink and stood up. “We could continue this conversation upstairs if you want to,” I started, and before I could finish she downed her drink with a smile and motioned me to lead the way.
Author: sir_cunning_linguist
[MF] Her First Anal Adventure
I got a text from Marie one afternoon that I feel like so many people dream of getting from their partners and it was straight to the point.
“I want to try anal.”
I was completely caught off guard but immediately interested, we had talked about it previously as a concept and she had never expressed desire to explore it so I wasn’t going to push. When I asked her why the sudden interest, she confessed that she had heard some friends talk about enjoying it so she had her interest piqued, and that she wanted to find out “what the big deal was.” We had been friends for a longer time than we had been friends with benefits so we trusted each other and that allowed a safe environment to explore. We began talking about it and decided to take the leap the upcoming weekend when we were both free next.
[MF] Her First Creampie, My First Squirter
Marie and I had been friends for a long time and after an extended period of both of us being single we talked about and opened ourselves into a friends with benefits relationship as neither of us had any real sexual outlet otherwise. Marie was short and chubby, dark eyes and long brown hair that fell past her shoulders. She was a 36DDD though, fair skin, and kept a somewhat full bush, I would learn.
It became a routine that she would come over with takeout and we’d hang out for a bit, we had talked about sex plenty but never had done anything until one night she started not so subtly by climbing over and straddling me as I sat on the couch. I could already feel myself stirring just having her warm body on top of me, as she slid her top over her head revealing the plain black bra underneath that held her voluptuous tits. I immediately grabbed them in both hands as I put my mouth to her neck and began to lick and kiss at her skin. Her response was perfect as she instantly shuddered and moaned on my ear. She eagerly reached behind her to undo her bra and set herself free, her tits falling out into my face, large pink nipples with areolas the size of a half dollar staring right at me. I ran my fingers across and grabbed each nipple between my fingers and began to pull gently on them as she leaned her head back, tossing her hair behind her giving me full view of her chest. I put my mouth to one and began to roll my tongue across it, feeling it harden in my mouth before moving to the other.
[MF] The Rebound (or how I stuck my dick in crazy)
Her name was Becky and she had been friends with Jess for years and had also been with one of my good friends for years. After things fell apart with Jess and I, she was also freshly separated and she made it a point to come to my comfort. Becky was a tall and busty milf (her son was two at the time and they shared custody,) with long sandy brown hair that fell between her shoulders, her bust was easily between a G and H, although she hid it well. She still had a bit of baby weight everywhere, but again she wasn’t unpleasant to they eye.
[MF] [F] Her Sister Watched Us
This story happened during one night where Jess and I had been going out to a show, and her sister Shelly had tagged along with us. Shelly was eighteen and quite frankly a brat most of the time, especially to her sister and I, however at their mother’s behest I had agreed to take her with us for the show. Shelly was similar in size and shape to her sister, but chubbier, longer hair and bigger boobs. She was notoriously promiscuous and dressed accordingly, tonight she had on tight black leggings and a leopard print tank top that barely contained her DDD chest. Pierced nose, pierced lip, pierced eyebrow, and dark makeup completed her look.
After the show it wasn’t too late in the evening and Shelly wasn’t eager to get home just as I wasn’t eager to finish my night without fucking my girlfriend, so we stopped at my house for a bit. We headed up to my room and Shelly sat in my desk chair and started to mess around on her phone as Jess coaxed me into making out on the bed. After a little while, and without looking up from her phone I hear Shelly say, “Look, you guys can go ahead and fuck already, I’m gonna put my headphones in and turn around.” She did so and being the horny young adults we were, we took the opportunity.
[MF] Valerie’s Visit, A Tale of Asian Temptation
This is the story of a visit I got from my friend Valerie while she came for a job interview in the city I was living in at the time. For a few years after college I was living with a roommate who due to his job travelled frequently or worked nights often leaving the place to myself for days at a time, and Valerie’s visit happened to coincide with one of those times. Val and I had gone to college together and had been close friends but nothing beyond that, I had been with someone through most of college while she had been single and now I was single and she had a boyfriend. Val was full blooded Chinese, about 5 foot 6, average build, long black hair about halfway down her back, c-cup and a fantastic ass. I was no stranger to imagining what she looked like undressed but that was something I obviously kept to myself.
[MF] Alone With Kate
Jess and I eventually hit a very messy breakup (not at all to do with our sex life, in fact we both lamented that loss) and there was a period where we tried to be some semblance of friends. Jess decided one of these nights that she wanted us and Kate to go out to a club, get drunk and just have fun. First off, I didn’t drink much, second, the club scene was the last place I wanted to be, and third Jess at this point was already drinking too much too often and I wasn’t exactly eager to be a part of that either. Still I wanted to try and salvage this thing we were trying to call a friendship so I agreed.
[MF] [FF] [Group] The Foursome That Came After
What would be considered a sequel to “Our First Threesome,” this is the story of the second encounter we shared with not just Kate, but also her boyfriend at the time, Joe. He was on the short side, average build, dark eyes and short black hair, typical run of the mill white kid. If you haven’t read the previous entry, Kate was a skinny pale Irish girl with a B-cup and full red bush. Jess was short with brown hair and was tan, tattooed, and a little chubby with 36DD’s and a shaved pussy.
[MFF] Our First Threesome (or how I learned her best friend was a cumslut)
This story takes place years ago with my ex (we’ll refer to her as Jess), and her best friend (who we’ll refer to as Kate). They were both 20, Jess was short and tan, a little on the chubby side, 36DDs, short brown hair and more than her fair share of tattoos across half her body. Kate on the other hand was a little taller, not by much and was pale and skinny as any 100% Irish girl would be. Longer red hair and maybe a B cup if she tried.
The fun started one afternoon with Kate hanging out with us at my place, the girls had always told me they were infamous for drinking wine together and talking dirty so I had gotten a few bottles and chose to put that to the test. After each had knocked back the better part of a bottle I hear them start giggling and I ask what’s so funny. Jess tells me that despite all their talk over the years they had never actually done anything or even seen each other naked… but now they were talking about it. I left them in bed giggling to go to the bathroom and came back to them laying side by side smiling in a sly and beckoning way. I slid into bed and naturally ran my hands towards Jess’s crotch but found her pantsless and there were already fingers there!
[MF] First Time Anal With Marie
I got a text from Marie one afternoon that I feel like so many people dream of getting from their partners and it was straight to the point.
“I want to try anal.”
I was completely caught off guard but immediately interested, we had talked about it previously as a concept and she had never expressed desire to explore it so I wasn’t going to push. When I asked her why the sudden interest, she confessed that she had heard some friends talk about enjoying it so she had her interest piqued, and that she wanted to find out “what the big deal was.” We had been friends for a longer time than we had been friends with benefits so we trusted each other and that allowed a safe environment to explore. We began talking about it and decided to take the leap the upcoming weekend when we were both free next.
She showed up after lunch and there was so much anticipation in the air between us, it was almost palpable. Somehow restraint held us, starting slow, we fell onto the couch and began to make out, slow and passionate, her hands pressed to my chest as mine ran up her sides. She began to unbutton my shirt, opening it and sliding it back as she continued to run her hands across my chest and I moved my hands to her front to feel her already hard nipples through her bra. She smiled as she took her shirt off, revealing the red lace bra underneath. Without hesitation I began to run my hands over her large breasts, pulling the bra slightly to expose her hard pink nipples from behind it. She giggled slightly as she reached behind to undo the clasp, letting it fall into our laps, her chest exposed and nipples erect with anticipation.
I dove in and began to kiss her neck as I began to pinch and pull at her nipples, her moans loud in my ear as she slid her hand into my hair, pulling gently before pushing my head down toward her nipples. I wrapped my tongue around one eagerly sucking and nibbling as I teased the other. I loved the feeling of her nipples hardening in my mouth, her gentle moans encouraging me to go further. I continued to tease her large breasts before moving my mouth lower down her body, passed her navel and stomach. I undid her pants and pulled them off to reveal the tiny black thong underneath, pulling it to the side exposing her wet lips. Moving my face close enough to smell her sweet aroma, she ran her fingers into my hair again as I gently extended my tongue to her lips and ran it a slowly the length of her wet slit. I slipped a finger inside her as I began to lick at her clit, she moved her hand from my head to spread herself for me, giving my tongue full access to her warm wet pussy. I added another finger and began to stroke that sweet spot inside her as I licked faster, adding pressure on her clit as I did. Her moans got louder as her breathing picked up and I was eager to lick the first orgasm out of her and before too long she came. I felt her legs shake as I licked and she didn’t gush this time but her pussy was soaked as she moaned and shook with pleasure. She leaned back with a content smile then slipped the thong off and she turned around, bending slightly over the couch and looking back at me. “Soo?” She teased with a smile.
I pulled out the bottle of lube I had bought for the occasion and squirted some just above her ass crack, she shivered a little at the cold and I let it drip down her a little before catching it with my fingers. I pressed my fingertip to her hole and applied just a little pressure as she moaned quietly in approval. I pressed my lubed finger and after a little teasing I slipped it into her tight hole with ease. I began to move my finger in and out to give her a taste, and added a little more lube to keep things sliding nicely. “Put another in,” she moaned softly and I obliged, as my second finger entered her without much resistance. Before too long she was starting to move her hips with the motion of my fingers, and I grabbed her ass hard with my free hand. I could feel her pussy dripping onto my thumb as I worked my fingers into her ass, and pretty soon her moans turned into words. “Fuck me, I need you to fuck me.”
“Ass?” I wanted to be sure.
“Mhmm” she confirmed as she reached back, grabbing her ass for me as I pulled my fingers out, wiping the lube from them. I applied a generous amount of lube to myself and her again as she wiggled her ass playfully. Sliding up behind her, I gently lined myself up to her waiting hole, already throbbing with anticipation as I pressed my cockhead against her. The moment seemed to carry on much longer than it lasted before I pressed against her and felt myself slide inside her with little effort. We both gasped a little as I pushed completely inside, her ass tighter and warmer than I was expecting, but the copious amount of lube made things much easier. I leaned back and pulled out a bit before slipping back inside her and her first moan was unbelievable sexy. She shuddered and moaned as I started to fuck her, she affirmed her enjoyment before I could ask and told me to keep going. I began slow and picked up speed a little as her moans coaxed me on. It wasn’t long before I could feel her tensing and suddenly to both of our shock she came, the orgasm taking over her as she moaned and shook, her tight hole gripping my cock as she came. She fell forward onto the couch, sweaty and hazy, but looking up with a smile as she turned to me. “I don’t know where that came from but holy shit I liked it.” I smiled back and motioned to my still very erect cock. “So?”
“Lay down,” she smiled, and I happily obliged, as she straddled my waist. “I’ve got something I want to try,” she continued, as she grabbed the lube and applied more to my dick, moans escaping me as she ran her fingers up and down my length. She applied more to herself again and lined me up with her ass, and seated herself on my cock with her visually soaked pussy staring right at me as I slipped back inside her other hole. “Jesus fuck,” I moaned as I felt myself swell and twitch inside her. She steadied herself with one hand on the back of the couch and ran her free hand down her body, her fingers eagerly reaching her dripping slit. She moaned long and loud as her fingers reached her clit, she began to rub herself gently as I began to push myself into her from below. I began to match her pace, as she sped up so did I, when she slowed, I eased off. We both sped up and as I really began pounding into her she lost her concentration and instead grabbed onto her nipple instead. She pulled and twisted as I pushed myself into her, her moans loud and her breathing heavy. I felt myself getting closer and closer and I quickly asked where she wanted it. “My tits,” she said without hesitation and she lifted herself off of me, one last gasped escaping her as I pulled out of her tight ass. She laid back and began to rub her clit again as I stood over her and began to stroke. I came quick and I came hard as I shot the first spurt of cum onto her chest. She continued to tease herself as I did the same, the sticky mess dripping down her chest as she slowed and stopped. I sat down, both of us sweaty and reeking of sex, looking down at her and asked, “Verdict?” She smiled contentedly then blushed a bit “I’d be willing to do this again…”
“I really didn’t think you were going to…”
“Me neither,” she cut me off, turning redder.
“But it was very very hot.” I smiled.
She smiled back a little sheepishly, then motioned to the mess on her chest.
“Shower?” I asked, she laughed and nodded in return.
After retreating to the bathroom I turned the shower on and we stepped in under the warm water. She began to rinse her large tits as I pressed myself up behind her. I took over running my hands up and down her nipples, teasing and pulling them as she leaned her warm wet body against me. I ran my hand down her front to her pussy, still wet and wanting as I parted her lips and slid my fingers inside her. She wrapped her hand up behind my neck and moaned into me as I began to caress my fingers inside her. She was sensitive and eager to cum, and I aimed to make it happen. I continued as I felt her legs begin to shake and before long she tensed into me, moaning and shaking, our soaked bodies pressed together. As she came down she turned and looked up at me, her long brown hair wet and clinging to her shoulders. She smiled and kissed me, and we took turns washing one another completely, lord knows we needed it that night.