My first blowjob

A hot past confession.

When I was a very young girl I had a gay friend. I met him in high school. I was young and totally virgin. But with a huge desire to suck dick. After thinking about it for a few months I asked him to let me suck his cock.

At first he flatly refused. I begged him for days. After a few days he barely accepted. We agreed on the day. We went to my house (I only lived with my mother and always worked in the afternoons).

He was very nervous. We went to my room. We laughed nervously and he turned on the TV and tried to distract me (we had limited time since my mother always arrived at 5pm and we left school at 2pm) I tried to hug him, kiss him and touch his cock. He retired nervously laughing. I got on my knees “kidding” in front of him, he was sitting. I opened my mouth and told him to put his cock in my mouth.

The Sissy Journal Vol 001

Day : 03/13/2019

Time : 1:30 PM

How : Gr****r

Where : His Place – House

Name : ? 001 ?

He hit me up on gr****r. We chatted and swapped pics. Sent girly pics first, then boy pics. He wanted to meet up right away.

I went over to his house in boy clothes. He lives only a few blocks away. I walk in…

As tall as me. Olive / white skin. Chubby Hairy Daddy Bear. Glasses. Cute.

We sit in the front room and I light a joint. We puff it once before clothes start coming off. I show him my freshly shaved legs and asked if I shaved all the way to my ass. Of course I do and he wanted to see. I strip completely and turn my ass in front of his face while he sits on the couch. He touches and spanks my ass. Then he stands up and takes his pants off. OH MY GOD, HE IS UNCUT!!! I have never sucked an uncut cock, so I quickly get on my knees to give it a try. LOVE IT!!! He likes deep head. He wanted to fuck me, and tried a few times, but I wasn’t “ready” ( I explained it to him after ) for anal. He stood over me and worked my mouth and throat till he was ready to cum. Asking where I wanted him to cum, I opened my mouth and stuck out my tongue. I let him cum in my mouth and kept in in for a little bit after. I spit it into a tissue that was in my jacket pocket. HOT ONE, HAVE TO DO IT AGAIN!

[M]y firs[T](Long read)

I thought I would share my first experience with a Trans girl which was one of the most amazing things I have done to date!

I am not gay probably consider myself Bi but haven’t gone down the path of sleeping with guys yet (who knows though!). To give you some background about myself I am a 6’1 Asian Male regular body nothing special.

So straight into it! I was recently single and travelling back to Asia to see my family and was feeling a bit horny on the night. Decided to go out with some friends to a club to see where the night might lead so we went to a popular night spot where people regularly hook up. Met a few girls here and there but didn’t really lead to anything so I decided to call it a night. Jumped into a taxi on the way home and was still feeling pretty horny at this point so I decided to jump onto craigslist (something I had always lurked on but never had the guts to try) but found alot of massage parlour ads (common in Asia). I then noticed the T4M section and thought what the heck! So I started to browse and found an absolute gem. Now I was completely new to this so I didn’t know what to expect and mulled on it for a little while. Finally got dropped off at my accom and decided to have a few drinks and finally sent her a text.

Well Endowed; A detailed sexual history of how I came to realize [M]y cock is huge.

I didn’t have the slightest clue or idea that I was well endowed until age 28. I have had a fair amount of partners, many of which dropped hints or made it abundantly clear, but thanks to porn and associated conditioning, it took me a very long time to finally recognize, understand and overcome a serious insecurity that my cock isn’t small, isn’t average, but actually is unusually large. Below is a brief account of my sexual history and all of the “hints” I received (and flew well over my head) over the years, leading to eventually overcoming this insecurity. Fair warning that this will read as a humble-brag, and to be honest, it more-or-less is exactly that. I’m writing this with clear eyes in hindsight. This is almost even therapeutic for me as at the time I was going through literally all of these experiences, I was seriously and shamefully in denial that I was large, assumed I was small and inadequate (thanks to porn’s misconceptions and a few select partners), thought every girl was just being nice & lying when complimenting me, and was constantly trying every thing possible sexually to be bigger and better to live up to the pornographic expectations from the clips I watched through my adolescence. I hope you either enjoy reading purely as a sexual experience or it helps you to overcome your own insecurity and that your cock is perfect, no matter what may you think or feel otherwise.

[MF] Cabin trip part 2 [more cheating]

First part and backstory found here: [https://www.reddit.com/r/gonewildstories/comments/b1eu5x/meeting_up_with_old_friends_for_a_trip_to_the/](https://www.reddit.com/r/gonewildstories/comments/b1eu5x/meeting_up_with_old_friends_for_a_trip_to_the/)

I left you off when we were in a giggly mood after getting each other off under the blanket, and we decided that we should go to bed. I was sharing a room with my male friend in the hot tub, and Ann was sharing with the girl. Very practical, so we decided just to walk up to them and tell them that they could have the girls room, we would take the boys room. They had not seen us earlier, and not noticing us doing our thing, so naturally they were quite surprised when we walked up, trying to cover up and pretending not having done anything wrong. I just finished with a “good night, and have fun” when i took Ann to my room. We were both exhausted, so even if undressing her and spooning her naked did not make it possible for me to do noting else than go to sleep with my semi-hard dick pressing towards her ass.

goddess transsexual in a hotel room

I didn’t know if the transsexual woman’s dick so deep in my ass made me gay or not, but I didn’t care at that moment. I just wanted her to fill me up and dump her load. The skimpy sundress I was wearing was now pulled down and up around my waist and creating a fabric handle for the woman to pull on as I was bent over taking her cock. my lacy stockings were still up and fortunately my high heels were still on, keeping my ass in a nice upright position with my head so low to the ground.

I had purchased the sundress and stockings that afternoon in preparation for my date that night with Betty. We had met online. She knew I was a wanna be sissy cock slut but had never acted on it. She was just happy to have an ass to dive her dick into. She was a beautiful but masculine woman. Much taller than me at 6 foot and a much bigger dick. She had olive skin that was so smooth and her implants were a good supple size, but not too big for her. It was a hotel meet up so there wasn’t much talking. I had rented the room and was fully sissified out when she showed up. She laughed at my attempt to dress sexy.

[M]eeting up with old [f]riends for a trip to the mountains. Old flames are not dead (cheating)

After a 20 year reunion from out masters degree, some friends suggested that we did a trip to a cabin in the mountains together. Since then we were mostly married or with partners and kids, some divorced and one deciding to go gay. Any how we all thought it would be fun to spend a weekend remembering and telling stories from our lives, doing some partying and exercise our skiing gear since it was in the Alps, early spring with lots of snow.

One of the girls, let’s call her Ann, and I had a special bond back then. Nothing romantic, but very good friends with “minor benefits” like kissing, massages etc. We also used each other for as cover or support if we got in a situation with someone else, getting unwanted attention, needing someone to call boy/girlfriend there and then, proving it with a kiss or something believably intimate. We shared beds also a couple of times, but nothing more happened. For some reason we did not talk more than 2 timed in the 20 years after school, busy with our families and kids.

So about last night [MF][Crossdressing][Pegging]

There is a weird and somewhat surreal thought exercise I like to engage in while sitting here in front of my company issued perfectly adequate yet utterly uninteresting laptop, over-hearing our office manager complaining again about people not refilling what I consider the world’s most inoffensively generic pot of mediocre coffee. I wonder ‘Am I the only kinky bastard in this room right now?’.

The high strung office manager with her ‘I want to talk to your manager’ haircut, has she ever been on the business end of a flogger? Jim in accounting, does he have some kind of smoking hot wife at home whom he just utterly dominates when he gets home, swapping his blue short sleeve button up shirt for a supple leather vest and single tail whip? My boss Kathy, with her exhausted eyes and comfortable but cheap shoes, does she have some titillating memories of the heady days of carefree left coast college explorative sex adventures?

[FM] I let my hairstylist play with me under my robe

I’ve never told anyone this story partially because as much as it turned me on, it does make me feel a bit dirty..

I was getting a coconut hair treatment done with my sister, she was on the chair right beside me. It was summer, so I was wearing a tank top that might have shown a bit too much cleavage.

This salon is not in my area, as my sister and I were away travelling. The stylist greets me; he was tall, skinny build, scruffy, brown hair – questionably gay at that (I don’t have the best gaydar).

[MM] My straight mate from work becomes curious

This is a true story that happened to me last year. After reading all the hot stories on here I though’t I’d finally share one of mine.

So some background. I used to work with this smoking hot straight guy called Jack (not his real name as I feel a bit weird about using his actual name). Jack was a super nice guy and we would always have a good chat over a drink after work. While being super nice he also had a cheeky side which would come out after a few drinks and we would often drunkenly flirt with each other till it went too far and he became a bit awkward. His gf also used to work with us and we would often joke about how I fancied him, which she was always cool about (all the girls in the office fancied him too so I think we was used to it). Boy did I fancy him too, I had more than a couple of wanks thinking about him. We worked together for a couple of years then both left the company at around the same time. We did the usual of promising to stay in touch and exchanged a few messages but it soon dried up and I heard nothing more from him.