[M]y night of [F]irsts

So, I was a late bloomer, sort of.

I did fine talking to girls and all, but as a somewhat overweight kid from pretty much birth up through, well, now, I had a MAJOR confidence problem when it came to actually thinking girls were into me. All through high school and college, up until I was probably 27 or 28, I just defaulted to thinking girls weren’t into me.

When high school ended, I was still a virgin. I’d made out, had a girl topless a few times, fingered a girl. But I’d never had my pants off, and I had certainly never gone down on a girl. I made it through my first semester of college with little more than that, not even getting what I’d managed once every six or so months back in high school.

Then came second semester, January weather, and a gift from god in the form of a six foot redhead with a tendency to decide she wanted someone at random and then Take. Fucking. Charge.

I ran into her as I was walking into my dorm building at something like eight o’clock one random Wednesday evening. She was hanging with a couple of friends, having a cigarette outside. I’d seen her around at a couple of parties, knew her name, she knew mine.

UPDATE: How swimming in [m]y underwear got me a hand job from someone else’s girlfriend [xpost from r/truebigdickstories]

Hey! So it’s been pretty quiet since the last update, but I had a great convo that I wanted to share! Here is the original post about the [hand job I received from my friend’s girlfriend](https://www.reddit.com/r/gonewildstories/comments/6py2nr/how_swimming_in_my_underwear_got_me_a_hand_job/) after [swimming in my underwear](https://www.reddit.com/r/Bulges/comments/5xhjqr/just_swim_in_your_underwear_they_said/). Update below:

I hadn’t seen Andy and Melissa since she sat on my lap and kissed me in front of him, but I’ve been thinking about her a lot, and have been daydreaming about this whole situation progressing further. I’ve been very hands-off and have been waiting for them to make the next move, and part of me was regretting it because I didn’t want this opportunity to fade. Things just picked back up recently though when I hung out with Andy and some other guys at a bar last week.

5 (a true story) [MF] [pegging]

https://imgur.com/a/4Fw4n

Dear reader, although I greatly enjoy reading erotic literature, I have not written much of it myself. Please be kind.

Preface
This is short story about a committed couple who are madly in love and enjoy role reversal and pegging.

Early October in New England after an extremely long day at work I am beyond elated to be home and see my beautiful woman, my queen, my Goddess. Greeting me with her brilliant smile she wore soft winter socks pulled up just slightly below her knees. Black booty shorts give way to her creamy strong thighs, and a string tank top that permit her full tender breasts to gently jiggle freely as she grants me a warm hug and kiss on my neck like she knows I like it. Wet and strong her open mouth on me as I breathe in her natural scent, floral, dryer sheets and incense.

His Name was Richard [f] [M] [oral] [anal] [squirt] [cum]

You’re asking me: How do you know his name was Richard? And I’ll tell you: I went to the mail room and looked at his mail box. I got his last name, got on Google and searched. Bam. Richard. 47.

He was a silver fox. He had short but stylish silver hair and a beard to match, muscles — so many muscles! And a few old tattoos on his forearms. I wanted to fuck him. I wanted him to fuck me. But I was too shy.

My parents bought me the apartment when I enrolled in college. They rented it out for two years and then, this year when I became a junior, I moved into it. My very own place!

I saw Richard on my first night in the studio apartment. He was on his balcony smoking a pipe. A pipe of all things. I thought, this guy is probably an author. Didn’t hurt my fantasy when he sat down and pulled out a thick book.

I started thinking about his cock and I wondered if it was as thick as the book he was reading. I just needed an in. I’m shy, okay? Too shy. I’m not like the girls in my school who send guys a pic of their tits and say “come over.”

I [F] watched the bride fuck another man [MF] (a bit long)

I made this throwaway about a month ago with the intent of posting one of my own stories but I feel like this one is better. As I said this is a bit long, because I tend to ramble a bit even when I’m writing. And ya I don’t think my writing is very good so feel free to point out any errors and such.

This all happened about 5 years ago, it was my friend’s bachelorette party. We had gone out and done stuff during the day and hit the hotel at night. We were in our hotel room, listening to music, dancing, drinking (just a little bit). It was nothing out of the ordinary. It was pretty late at night, almost 2am and I was considering heading hack too my room to get some sleep. This where slowing down in general but things picked up pretty quick.

[MF] Fulfilling her fetish.

Long time lurker finally deciding to share a story after being reminded of it by former fuck buddy. I ran into Cindy (former fuck buddy) recently and remembering it has got me somewhat hot and bothered so I thought I’d share. I’ll mark the actual dirty bit with a *** for you impatient people lol.

A few years back Cindy and I volunteered to work at our former high schools fireworks booth during the 4th of July weekend. I was 19 or so it was my first year in college and Cindy was 18 and just graduated that year.

Cindy despite being a band geek is actually quite athletic, she was a soccer and track star at our school and during the summers she’d work as a life guard at the pool. She is a tan white girl that has blonde almost golden hair and icy blue eyes. She has a tight little body no taller than 5’0 maybe 5’1, with perky little tits and a nice tone ass.

I am an Asian who luckily was born with broad shoulders and at the time had a fairly muscular body. I’m not all that tall standing at around 5’5.

[MF] Coworker through the window [cheating] Part 1

**Be warned, this story involves infidelity. Also, it is pretty long and only really covers the first part of an ongoing affair.**

I am 32M, married, just over six feet tall, brown hair, green eyes, and average looking. My coworker will be called Jody, 40F, also married, about five feet tall with curly brown hair. She has a small frame with some residual weight through the middle from having two kids. Her breasts are on the larger side, maybe 34DD, but she tends to wear loose fitting blouses or sweaters, probably because she is slightly self conscious. Jody’s conservative wardrobe contrasts with some of the younger office employees’ outfits, and give her a hybrid mature/girl-next-door vibe. We have worked together for over five years, and we get along really well. However, we never spend time together outside of the office, so it is more of a “work spouse” situation.

Cock starved[FM]

Getting married too young is bad for you, the lack of emotional maturity will eventually push your marriage into hell and with kids you opt into staying together while you grow angry and unsatisfied. After being married for more than 12 years, my husband began to cheat on me and I was perplexed with the why. I’m a healthy 27-year-old with curves and I consider myself attractive, my guess was that I was sexually daring. But then again I always wanted please him, but it wasn’t enough for him, so instead of blaming myself I decided to look elsewhere as he kept refusing to have physical contact with me.

I thought that I will never cheat. However, the last couple of weeks it has escalated to the point that I could say I have had the best sex in my life and not with my husband.

“Tell Me What You’re Going To Do.” [MF] [Anal] [Strapon]

I almost ran up the steps toward the apartment, followed closely by my girlfriend Trisha. The whole time I was at the play, this was all I’d been thinking about. It wasn’t a bad show; I just couldn’t focus. I just sat there next to my girlfriend for two hours, with my hard member stretching against my jeans, thinking about what would happen when we got home.
As soon as we got inside, we locked the door, turned on some gentle mood lighting, and pulled some beers out of the fridge. We popped the tabs and drank, and then we crawled into the bed. We kissed. Not a slow, gentle, shallow kiss, but aggressively, exploring each other’s mouths with our tongues, occasionally biting. I was already rock-hard. I had been ever since we’d stepped into the apartment.
I slip my hand under her shirt, over the curves of her hip and back, and undid her bra with one quick motion. I felt her lips curve into a smile, and I moved my hand to the front, cupping one of her breasts. Her nipples were hard already, but I played with the breast a little first, squeezing, teasing. I lifted her up, and pulled off her shirt. As I moved downward, aligning my mouth with her nipples instead of her lips, she pulled mine off as well. I bit down, gently, and started flicking my tongue past her nipple. Her breathing pattern changed, just a little, and I knew she was ready for more.
I unzipped her pants, and cupped her smooth mound. I moved my hand, gently, teasing, before I slipped my fingers in between the lips and began moving in gentle circles over her clit. She moaned, quietly, but then moved away.
She only moved to get her pants off, and then took mine as well, adding it to the pile on the floor. I kept touching her, like I had been – my fingers playing with her clit, and my tongue gently massaging her nipples. I shuddered as she slid a hand between my legs. She moved it slowly up my thigh, cupped my balls in a brief hello, and then moved back to my hole. Her finger’s caress on my sensitive skin sent a little jolt of electricity running through my body, and it continued as she massaged gently.
“Are you ready?” she asked.
I took my mouth off of her nipple and nodded. She got up, and gently pushed my head down onto the bed, leaving me on my knees with my ass in the air. She spanked me, harder than usual. She knew I liked it. I closed my eyes, focused on the sensation. Suddenly, I felt her breath, and then her wet tongue gently caressing my hole. I moaned, and did my best to relax. I felt some of the tension dissipate as she licked, over and over, and then gently begin sliding her tongue in an out.
Then, she stopped, and I saw her reach for the bottle of lube next to the bed. I spread my legs a little wider, preparing, and then I felt the cool tip of a glass buttplug make contact. I relaxed as much as I could, and eased back onto the toy, letting it gradually spread me wider. I practiced this relatively frequently, and I didn’t feel any discomfort until the widest part. I moaned as it slid in, its cool weight pressing gently into my prostate.
She pushed me gently out of the way and then laid down, spreading her legs.
“My turn first,” she said.
I crawled to the space between her legs and leaned in, inhaling her scent. I kissed around her soft lips, teasing, and then spread the lips with my fingers. I started low, near the opening, and worked my way up to the clit, savoring the taste. She was holding her breath, waiting. I closed in with my mouth, pressing my tongue into her, blanketing her wet clit with my tongue, and then I started moving. Up and down, slowly, then faster.
I slid a finger inside her and curled it toward me, moving in circles. She moaned. I pressed myself into her, holding her tightly with my free arm. I was so aroused, I felt like I was in danger of cumming just from the way my dick rubbed slightly against the bed. Trisha’s body tightened, tried to jerk away, as she moaned louder, but I kept her where she was, kept moving. Her moaned grew louder until finally they became a scream of pleasure. She spasmed in the throes of her orgasm, and then became still.
I laid down next to her. Usually, she took time to recover afterwards, but this time I could tell she already wanted more. Her eyes were still hungry. She propped herself up on one arm, above me, and ran a hand over my side, like I sometimes did to her. I quivered in anticipation of the coming pleasure.
“Tell me what you’re going to do,” I breathed.
She leaned in close, so I could feel her warm breath as she whispered into my ear. “I’m going to make you mine. I’m going to take you. Slow, at first, and then faster, harder. And I’m going to make you cum with me inside you.”
I shuddered. I was ready to be hers. She stepped off of the bed and slipped a harness on. I watched her tighten the straps that held her blue penis in place. It was almost exactly the same size as my own, and it looked great on her. I turned and got into position, on my hands and knees, and she got behind me.
“Spread your legs wider,” she commanded. I’m not to flexible, but I complied.
Trisha grabbed the plug and slowly pulled. Once again, it stretched on the way out at the thickest point, but it felt noticeably looser. I could feel that once it was out, it didn’t quite close all the way. I felt Trisha put a hand on my back, while the other hand guided her penis into me. It felt much longer than it really was as all six inches slid into me. She placed both hands on my hips, just like I did to her when we did it doggy-style.
I moaned as she slid out, and then back in. It was slow and gentle, just like she’d said it would be, but the sensation was already extremely intense. I could feel the tip of her penis massaging my prostate, and it felt deep. She started speeding up, fucking me harder and faster, and I moaned even louder. I felt like a girl, sometimes, but I don’t care. She makes me feel good.
Trisha’s hips slapped against my butt cheeks as she pounded me, sliding the entire length of her penis in and out of my ass, and her hands gripped tighter. I was almost screaming. Suddenly she stopped, and pulled out.
“Lie on your back,” she said.
Once I had changed positions, she slid it in again, the full length. I moaned. It was so intense, my entire body felt weak. My ass tightened involuntarily around Trisha’s penis as she wrapped a lubed hand around my dick. She started moving the hand, as well, and my body became a mass of electricity. I felt her deep inside me, still moving, while her hand slid up and down my cock. I couldn’t last long, this way.
“Make me cum on myself,” I heard myself gasp, as the feeling became too intense to hold in.
My entire body spasmed as I came, like I was a girl in a porno, but none of this was faked. Fireworks went off in my entire body, and I think I went blind for a few seconds. I felt hot droplets of my own semen splatter across my chest and my neck, and I loved it. I was hers.
Trisha pulled out, and I spasmed. I was so sensitive, every movement felt like electricity. She undid her straps, and the dildo fell to the floor. All I could do when she laid down in the bed next to me was lay there, staring at the ceiling, my mind still scrambling to reconnect with my body after the best orgasm of my life had ripped it apart. I was hers.

The day I got caught by the [M]aid

This happened my years ago when I was a teenager.

We had a lady cleaning our house once a week. She was a nice single mom in her 40s and not extremely sexy. She came from a conservative background and dressed accordingly – always in a worn out dress that hid her thick ass and heavy tits.

Being that age, I did what every teenage boy does – I would masturbate pretty much the whole day long whenever I could and wherever I could. Keep in mind there were no smartphones or internet – just worn out magazines and mostly imagination.

So that particular day, I decided to skip school and stay at home. I totally forgot about Rita (lets stick to that alias) and when I woke up with a raging hard on – I didn’t think twice, threw the sheet away and went at it full speed ahead fantasizing about some chicks from school with my eyes closed.