My most recent time fucking a crossdresser [M28, T19]

I’ve always had a voracious sexual appetite that has led me into the rabbit hole on more than a few occasions. For my first story, I’m going to retell my most recent night with a crossdresser. This happened in February 2016 and is as accurate as my memory will allow.

I’m 29, tall, a fraction overweight, but I would imagine reasonably attractive. I am single, live alone and have no dependants. I did well at school and at university, and have found success in the financial sector. I am not objectively rich, but do make a six figure salary and have the toys to go with it. I only mention that as for the purpose of some other stories, I have managed to use it to my advantage to sleep with women very much out of my league. Sexually I am very much of a hedonist, but in my day to day life I am boringly ordinary. I do not drink, do drugs or smoke. My cock is just a hair over 7 1/2 inches, although it’s not particularly thick. It’s perfectly straight, something that has been commented on by lovers a few times.

After Practice Pleasure [NSFW] [M] [mast]

I came home after football practice – or “soccer” – to those who give a shit about using their own terms. I was tired, sweaty and had one shin badly raked by spikes in a tight tackle gone wrong. Don’t fret; I absolutely hammed the fucker who did it to me about 15 minutes later.

I half limped over to the fridge to see what I might snack for supper. Nothing worth eating, perhaps a takeaway curry later? We’ll see, not too hungry at the moment anyway. Nothing on the telly either, and my girlfriend has been away visiting her mother in Cardiff. Slightly bored, I was, so what was a 21 year old feller to do? As I hadn’t had any action (other than footy) for days, an answer to this burning question was not very far away.

I peeled off my guernsey, lay on the bed and fired up my laptop. You know what I had in mind just as well as I did.

She Was The Perfect Hotwife [mmf] [swing] [oral]

Like most men, I find myself browsing pornography on the internet from time to time. It’s fascinating moving through a trail of various sites linked together by user comments and submissions. More often than not i find myself in a place far different from where i started, only a faint recollection of how i got there. I guess that’s the only way I can explain the events that led to my encounter with a couple from Reddit.

I’d spent a few months browsing the wide array photo’s and videos available on Reddit and was quickly pulled into the user generated content. I was amazed at the amount of incredibly hot stuff produced by everyday people willing to share. Before long I found traditional “professional” pornography to be humdrum at best and sometimes downright offensive to my sensibilities. The more time I spent exploring this new world of real people sharing themselves the more I became seduced by it. I couldn’t help contemplating the desires of the subjects and those who shared the images. There’s or course the base desire to share things in order to; boast, be admired, participate, feel part of a group or to stand out from the group.

Valentine Lingerie Party [Str8, Les, exh, swing, creampie, cheat, cuck]

My girlfriend and I went to a lingerie party on Valentine’s day. It was hosted by a friend of hers who has always been a bit wild. Candice and I met in college and have been dating exclusively for five years. She keeps hinting that she wants to get married, and lately the hints are less subtle and more, “oh lets go check out these engagement rings in this jewelry store.” I definitely love her and I’m sure she’s the one, and I’ve bought a ring. I just haven’t popped the question yet.

In college we were both kind of nerdy and overweight. When she got a job right out of school, she made some new friends who convinced her to start dieting and exercising. She lost 40 lbs. Her waist shrank, but her boobs stayed pretty big. I’m not complaining, because I get to play with them every day. She also started experimenting with makeup more, and bleached her hair blond. I noticed all the changes and it made me self conscious so I joined the gym too. I’ve lost 30 lbs and I’ve put on a lot of muscle, but I got a later start and its been a bit slower for me. So Candice has gone from like a 6 to (no lie) an absolute 10, and I’ve gone from a 5 to maybe a 7.5. Candice started telling people to call her Candy, so now I feel like I’m dating a porn star.

Unexpected fun at the Massage (m/f)

So to start the story I’m going to tell you I’m a big perv, not going to deny it. For at least 8 years I’ve been visiting this little rub and tug in my town maybe three or four times a year. The ladies that work there, or rotate in and out give absolutely mind blowing massages. You wouldn’t think that would you? If you’ve never been to a tizzug as my good friend J-roc would call them, you probably just assume it’s a quick hand glide over body, machine gun jerk and you’re on your way. Mostly true, however sometimes you can find a place where you can get a massage on a professional spa level and get a little handy at the end. The perfect combo!

Well after a 14 hour day on the job I was in need of a little pick me up, so on my way home I decided to stop in at my usual spot. They are open till 2am and I can shower there since I smell like axle grease and hydraulic oil, which I can imagine isn’t pleasant to someone who is not used to it.

Jackson [MFM?]

Jackson

I had lost two stupid cases in as many preceding days. I wasted time after I got home from work because a girl that works in my office, that I have had sex with, said in her emailed invitation to happy hour that it went until 7. So I changed into my finest lumberjack/hipster/skater attire, drank two medium-sized glasses of rye whiskey alone, and ambled down the sidewalk to the designated bar which is five blocks from my house.

Arrival at 7:15 and nobody was there with the exception of a young woman from my office who was still attired in her somewhat ill-fitting suit from doing her own trial that day. She informed me that the others had been there, but had left prior to 7pm, babies.

Had my [M] first jerk off buddy [M] today, things escalated quickly

TL;DR: found a jerk off buddy after a year of looking at this stuff, but the jo bud part lasted 10 minutes before it goes into make out, kissing, bj and 69. Did satisfied both my jo bud and bi-curious side in an hour, feel good now!

First off, its been almost a year that i stumbled onto r/jobuds subreddit and since then I was hooked to the stories and the community. I had a few jerk off sessions on kik in and off during the year.

I lurked on craigslist last week because I wanted to “get done with it once and for all” and actually do a real jo session with another. Found a guy that was about my age and shape, but the wording of the post sounded that he was more gay than straight bi-curious. I didnt mind because im a bit bi-curious so i wouldn’t have minded if during the jo session we would stroke each other.

The Turning [NSFW] [M/F] [Oral]

I was enjoying a quiet sit down in the park that Thursday afternoon, coffee in hand and the sun on my face. A perfectly, warm autumn day. I took a sip of coffee.

“Ah-BOO!” my interloper yelled from behind me.

I almost dropped my takeaway cup on my lap, dislodging the lid in the process. Coffee dripped through my fingers and sprinkled over my shirt.

“Hello Kelly. You’re late”, I said, ignoring the provocation. It would never do to appear rattled with this one. She would enjoy it too much.

The girl sat down on the grass next to me and took a cup of takeaway coffee from the disposable cardboard tray next to me.
Please meet Kelly: a jolly elf of a lass, 27 years old and quite stunning. My only complaint, if I should be forced to own one, is that her hair was cropped too short for my liking. She wore a Ramones t-shirt, blue jeans and sneakers. Or, as I tended to think of it as – Kelly’s all round year uniform.

“Hardly late”, she replied. “Blame the bus, Mr Anal”.

Achieve[m]ent Unlocked: I Sucked on a Penis

Since I was about 16, I had thought about giving oral sex to a man. At this point, I hadn’t even given oral sex to a woman, much less received it from anyone, but I had a desire to try it some day in the future. When my parents kissed me goodbye outside my dorm, the future was here.

Sucking a cock wasn’t the only thing I wanted. I had assembled somewhat of a sexual bucket list that I planned to attack in college. It mostly consisted of pretty standard fantasies: have a threesome, give a facial, have anal sex, have sex in public, etc. At this point, I was very inexperienced, so there were a lot of firsts to be had.

As soon as my parents drove away, I headed straight back to my dorm and got on my computer. This was about 8 years ago, long before I had heard about reddit, so my go to medium was Craigslist. I had browsed the personals in the areas around my home town before, but never had a chance to actually meet with anyone. I couldn’t exactly bring a stranger over to my parents’ house for some anonymous sex, and I don’t think my dad would have let me use his car to drive to a casual encounter.

Worst Roommate [MF, voy]

After graduating from college, I moved to a new city and managed to live in a house with two of my friends who I knew through school. We saw each other throughout the four years together and knew each other well enough that we figured becoming roommates would be a good fit – which it was. For the most part, we all continued to act like we were in school still – except substitute classes for an actual job. We’d go out a couple times a week, have people over, play beer pong in the summer, and play video games together in the evenings. So overall we were great friends who were living it up in our early 20s.

After a few months one of my roommates, Sean, began seeing and dating a girl named Elise. At first it was just a fling type of thing where we would see her at a bar and she’d come back to the house with Sean every so often. Sometimes they’d plan to meet up beforehand as well. Over time though it became a relationship and we saw Elise a lot more. She’d stay the night and hang out with us during the day. Watch movies or play video games with us as well.