Answered a craigslist ad from a guy willing to suck off straight guys, got more than I bargained for [MM]

*NOTE: I posted this story once before years ago on a different account. But I deleted that account and have since made a new one. I want to tell this and a few other stories and figure I should do it all from one account.*

I should preface this story by saying that I am straight, generally, and had never been with a guy before this story. This was a few years ago, when I was 24, living in New York City and dating a girl long-distance.

My girlfriend and I had been together for a few years, since college, but an amazing opportunity took her to another city for two years. I found myself on the Greyhound a lot and, when I wasn’t with her, often sexually frustrated–especially as I saw all my friends living it up as single guys in their twenties in NYC.

Surprise First Anal [MF]

Bored & feeling the need to touch on a good memory. This happened back when I was 25 and she was just a few months older. We took a trip up and down the state during a long weekend to see our favorite bands on opposite sides of the state. We were happily in our relationship for a couple years at this point, with a libido that matched our ages and obsessive nature we had towards each other. This meant many hours in the car, ranging from alien talks, to work, to dirty talk with some light playing/teasing while I drove.

We got into our hotel at a decent time and had a night to spare before the second concert. After we checked in we went full-on 15 year old, making out and getting gropey. When checking into hotels, we would always ask for two beds (making us look like good-Christians) while in reality we really just wanted to have a sex-bed and a sleep-bed.

After a days worth of teasing in the car and chafing my cock against her dress, I was over it. However, she was ready to eat and wanted to keep the tease going as long as she could.

[M]adly in love, [F]rantic petting

Long time lurker, first time poster. I thought I’d share some of my experiences. This one is relatively tame but it’s one of my favorite memories. 18+ disclaimer.

We were young, and madly in love, the way that only hungry high schoolers can be. She wasn’t the girl next door. She was the girl two houses down from my mom’s house. Ella was tall, taller than me, and thin. Leggy and still awkward in her high heels; she reminded me of a fawn, unstable and unsure of her footing. That look, those almost stumbles, those knocked knees in miniskirts, hurt my heart even today, as I stare down the barrel of 40. She had dark hair, thick and straight, past her long pale neck, down to her shoulders. Big doe eyes with heavy lashes, she liked to give me butterfly kisses, curled up at my side on the couch at her parents’ home. Her chest had outgrown her body that summer, and most of her tshirts, and she knew it. 36 DDDs, a tiny waist, almost no hips yet, and those legs, legs that went on forever.

Getting her into anal play and stretching her ass. [MF] Long, very detailed

Sorry it’s been a while everybody. I’ve been balancing work and applying for school which I officially got into. Tulane bound come January. Anyway, me and Brittany have made a lot of progress in the bedroom. She’s opened up and tried a lot in the 3ish months we’ve been at it. Enjoy.

Brittany is into the buttplug now. She still takes some warming up, but I genuinely enjoy all of that so win win. For maybe the last 3 weeks we’ve been testing the waters with ass play. So far her favorite is a tie between rimjob with her vibrator and finger in the ass while she’s bent over getting fucked. To quote her, “when you use your tongue, it’s like a really gentle massage in a spot I’ve never had a massage. Pretty much sensory overload” which is a pretty good way to put it. So this took place the weekend before Halloween. We had a party to go to Friday and Saturday. I teased her about the idea of wearing it out and she nervously wagered what she wins if she can manage it in until we get back home. So if she can’t do it, no clothes all Sunday for her. If she does, she has a week of on call oral sex for any reason at any time. Another win win.

Exposing Jessica [MF] [exhibitionism]

This is from back when I was in college. I’ve been thinking about it a lot recently and thought a few of you might like it.

Jessica was quiet. Shoulder length, straight black hair, caramel eyes—she was pretty, but often overlooked in a crowd. We had been friends since freshman year, and like most everyone else it had never occurred to me to look at Jessica as anything other than a friend. She had a small apartment off campus, and after class we’d often hang out there.

One night we were on her couch watching some show when two of her girlfriends showed up unexpectedly. When they came into the room, everything changed. They were drunk, flirty, and one of them, I don’t remember her name, was showing off her new digital camera. This was the early 2000’s, and at least at my school, digital cameras were rare. I remember being a little annoyed when they first showed up, but in retrospect, they were the cause of one of the best nights of my life.

I was mixing drinks in the kitchen. The two friends were on the couch taking pictures of their cleavage and Jessica, as always, was sitting in the big armchair in the corner quietly watching it all.

[MF] It took moving out of the apartment to finally lay my former roommate.

Quick backstory: I went to high school with a girl and we were friends but never super close. We ended up going to the same University and hung out quite a bit our freshman year and then moved in together our sophomore year. But by this time, she already had a boyfriend. She has dark hair, tan skin, about 5’2″ and couldn’t weigh more than 110lbs. Athletic; she played tennis in college. Very petite and tight body. I am 6’1″ 190lbs with an athletic build and am very shy in general.

Being from the same hometown, we would drive home together for holidays to save on gas. One trip back to college, we played a strip game in the car. I was driving her car and she kicked my ass in the game, but knowing she had a bf, I never took any clothes off. A missed hint on my end. On another occasion, she was getting ready to go out for dinner with her bf for their 1 year. She called me back from my buddies apartment (2 minute walk away) for me to help her pick out a dress. She tried on a handful of dresses for me to judge which one looked best on her. She also changed dresses in front of me and me being innocent/shy, missed another hint. I never saw her completely naked because she had a strapless bra on, but she sure looked fine as hell in her underwear. The lasthint I missed/ignored, since I knew she had a bf, is she called me to pick her up when her car broke down. Not her bf. She asked how she could repay me and I told her to not worry about it.

How I Finally Fucked an Old Acquaintance [MF] [Cheating]

(All names have been changed, because y’all pervs) :)

Right after I graduated college I met Megan one warm summer evening at a drunken music festival. At first glance, I kinda thought she was a little bit stockier than I normally go for and didn’t really take too much notice of her. But as the night went on and we got to drinking and talking I slowly started getting drawn to her playful smile, sharp wit and mostly, her sense of innocence that seemed genuine yet unbelievable at the same time. As the night progressed, and more beers we’re downed Megan and I ended up drinking a bit too much, and we moved from conversing to getting handsy with each other and giggling like school kids with crushes.

[MF] [MT] My Thailand Ping Pong show adventure

For warning, this is a long story.

While I served in the US Navy I had the opportunity to travel all over the world. One such place is a far away magical land called… Thailand. I know what you might be thinking and yes you’re probably right. Before I get too far along I will assure the reader my story does not include any underage sexual encounters.

It all begins on a US Navy aircraft carrier called the USS Abraham Lincoln. And a young seaman who was T.A.D. to the Chief’s Mess (that’s me). Through some tomfoolery, I had accidentally broken my thumb. Well, more than just broke it. I had broken the tip of the bone clean off and nearly severed the flesh completely. Why is this relevant to a ping pong show in Thailand? Well, this all happened just a week before the ship made it to Pattaya and this horny sailor was prescribed Vicodin. Did I abuse my prescription? Some would say not enough.

Stripping At Parties (Part 2) [M]

**House Party for my birthday**

This story was a tad bit more straight forward. A friend of mine we shall called Brad said I could hold my birthday party at their house. My friend Liam had gotten me a bottle of vodka for the occasion and maybe wasn’t such a good thing to get me.

As the party got into full swing, I was dancing in the middle of the room. I don’t quite know how it happened but I ended up stripping down to my underwear in a room full of my friends. It was happened pretty quick. Then I had to get Sally to remove my underwear, I didn’t have to the guts to do it myself. I kept my socks and boots on this time as well.

This was when things went sour cause the adrenaline of being nude, mixed with the vodka I had had. I needed to throw up and ran to the toilet. I’m pretty sure I didn’t cover myself when getting sick in the toilet, also Brad had opened the window to the room and was taking pictures of me. There had been some taken whilst I was stripping too.

Asking my roommate to join my boyfriend and me [FFM]

I posted an original story on another sub about asking my roommate if she wanted to fool around with my boyfriend and I and she agreed! Here’s the first update on what happened after that night. I copied and pasted most of this story from one of my other posts, but this one will have an extra update due to more happening with this situation since my original post.

My roommate has never experimented with anything like this before, most of the guys she’s been with gave her vanilla sex. It makes sense seeing as she’s only 18 and freshly out of high school this year; my boyfriend and I are both 20. So my boyfriend, we’ll call him L, decided to start a conversation with her one on one to see how comfortable she was with everything since I had talked to her. They started trading pictures and he told her how excited he was for us to get back home. Last night she told me she would be more comfortable if she watched us have sex before getting involved so she could get an idea of what to expect. I told her L and I had made plans to hook up that evening so it was perfect timing.