So tomorrow I am going to have my first gay experience. My fiance finally talked me into it after 2+ years. She wants to watch another man give me head and then see me fuck him in the ass. She is just going to sit and watch after showing him how I like to get head. I've never been with a man before, so in preparation we've been watching a lot of gay and shemale porn on here. It has been an incredibly liberating experience so far. She has fingerd my asshole and used anal beads on me in the past to great effect, and I am extremely excited about tomorrow night. I've got good condoms and lube, and I'm going to fuck his ass good. (we found him through an ad on craigslist)

Warning: gay, crossdressing and trap stuff in this post.

I confess that i am kind of addicted to womens underwear, i had gay experiences and here are some of my adventures.

First of all a bit about this panty and crossdressing fetish:

It started a few years ago, my brother had a kind of hot girlfriend, maybe 7/10. I found hear panties and strings in the laundry and the smell turned me on. i used to masturbate to or into them.
I befriended her family and her twin sisters in my age. We used to go to the same school and everytime i was at their place, i used to go trough the laundry on the bathroom and smell their panties. i found it to be super hot especially when they started wearing thongs.
I used to be in a relationship with both, but it wasn't for a long duration. I had the opportunity to see and touch their pussys multiple times but it never went further. I still ask my self why i didn't pushed things but i guess i was just too embarrased by the situations. To this day, about 4 years later, i still smell their panties if i am over at their place.

In those 4 Years my father found a new girlfriend and she moved to our place together with her daughter, same age as me. She wasn't good looking maybe 5/10 but her body was nice.
A few months later i started hooking up with her, but she was very childish and i got basically cockblocked by her embarrasment. she even thought that masturbation would be gross. She teased me many times with stuff like humping me a bit or pushing my face between her legs, but everytime i wanted to go further she went back and told me to stop. i knew it made her wet because once she went into the shower after teasing me again and i smelled her panties afterwards and they were wet.

This was around 2 years ago. Today she had a bunch of boyfriends for short durations and noticeable many female friends over. One of them lived at our place for about 2 weeks and it was like wet panty heaven for my panty fetish. anyway i looked trough her room and found condoms, lube and dildos under her bed. One of the dildos was a double ended one. the look and imagination of her having sex with her female friends gave me and instant boner.
I found her lingerie stash, everything in a big box. I went trough it and got turned on to the max. i just had to try them on so i wore a pair of stockings with a string and a corset like top. i had the feeling to have the largest boner in my life so far and i went further, i kept wearing the stuff, got into my shoes and jacked and went out with our dog for a walk. (Little note: my parents are on vacation for a few weeks and i stayed home alone) It was already dark and i live in a rather quiet place. At this time almost no one is on the streets. My dick was building a little tent under my jacket the whole time and i had to dodge two people but i came back home without beeing seen. (atleast i hope so) I sat down in the lingerie and started fapping. It was an impressing orgasm but not the best i had so far.

Now to the gay stuff:

I have a friend that i know since preschool. he was my best friend for a long time and after puberty we started to do some "experiments". We basically had anal sex everyday after or even while we are in school. It was almost always me fucking him because i hated the feeling of it. I started trying that stuff with dildos i found, mentioned above.
I slept over at his place or he was at my place and we would always watch porn or do some roleplay. sometiems one of us even prentended to be a girl. Our last session was around 1 month ago. he was home alone and we had some fun with his sexdolls, but we ran out of lube so the sex was literally a pain in the ass. we stopped it and continued sucking each other off instead. I like giving blowjobs but i hate cum.
We even played a few games like hide & seek and the one who gets found within 2min must strip one piece of clothing off.
We explored the room of his milf (maybe in the late 30's. pretty nice body, blonde etc) and found some anal beads, handcuffs and a strapon. That thing was huge, he tried fitting it but it was too big.
At the end he fucked me with the help of the rest lube and spit and he came in me. Since he always looses his mood in and instant, i had to fap with his pockedpussy.

A few days later he was over at my place and we basically did the same stuff expect that i sucked him off and he came in my mouth. i went to work later, still with the feeling of his dick in my butt.

Then there is this other guy who i know since highschool.
We used to be good friends and we did normal stuff except that we fapped together to porn sometimes.
We once had this girl who was showing off on the cam and we sent her some dickpics of us. she continued to fap to them and my friend said what i would give him if he would suck my dick. i said idk and he started to open my pants and suck my dick.
I knew where this was going to i started to give him a handjob while hes doing it and damn is cock was like triple the size of mine, even though he was only a year older.
He seemed to like sucking it because he did it alot in the next months, maybe even a year. i dont remember. then there was this one night. i was sleeping over at his place and he was home alone. he played some games and then he went out of the room and came back wearing stockings and other lingerie and even a latex corset from his mothers friend. she was living at their place for a bit because her husband kicked her out.
We did some roleplay and i proceeded to suck and fuck him. after i came gloryously in his ass, i continued to suck him off, because he didn't liked the feeling of fucking me. It was the first time someone came in my mouth and it wasn't that bad as i expected it to be. The warm and salty taste still surprised me a bit so i spit it out and made him laugh.
After that we didn't really do anything anymore because i had a girlfriend then (mentioned above, the 5/10) and later he got one himself.

So this is basically a confession about my dirty adventures i had so far. I felt like i should share it with someone.

My current female partner is frigid, I've been curious for quite some time, so out of frustration I decided I would try and find out 'how the other half live':

I joined Cottaging.co.uk and was fairly quickly contacted with compliments on my cock pics, and was contacted by a guy a few towns away that was interested in all sorts of fun; the real 'deciders' were that he wanted to play with me in my Pretties, and he sent me a set of pictures of him and his Fucking Machine! He was to be the Dom on our first meet; I pulled up to his house with the instructions not to knock, just to walk in - he would be in the living room waiting for me. He wanted me to arrive 'normal', then go and shower and remove all body hair below the waist, then dress up for him, then we'd start playing. Sounded good; gave me time to mentally prepare for this thing I'd never done before whilst preparing physically and with my clothing.

However he was naked on a reclining sofa, watching gay porn on a laptop when I arrived - not sure what I expected, but I got over the shock and sat next to him at his invitation - me on his right, still fully clothed in work gear, his laptop to his left, and him slowly stroking his (fairly small 4 and half inch) cock. The scene on the laptop had literally just ended and a new one in his playlist began, with the inevitable touching leading to sucking on-screen. He took my hand and wrapped it around his cock in line with the on-screen action, so I stroked it for him - shocked to be doing it so suddenly, but hey - that's what I was there for really, right!? Maybe I should have suspected something when his now-free right hand started carressing my back, but I'd never been in this situation, so what seems obvious now was all new at the time. As the guy on-screen went down and engulfed his partners cock, this guys hand grabbed the back of my head and pushed me down onto his cock, removing my hand to free the way - just like that my mouth was full, his balls were pressed against my cheek, and using my hair and his hips he was fucking my face. Just like that. No warning. And the biggest shock was that I LOVED it! I gagged a few times but stayed there, basically being used, until he pulled me up off his cock and told me to go and get ready. So I used the shower and liberally coated myself in Veet, removing all necessary hair, then dressed, and finally flushed using his shower head as an enema to prepare my ass for action.

A Sissy Slut padded back down the stairs in black stockings, suspender belt, Corset and see-thru mesh knickers with turquoise lace, matching the turquoise mini skirt I borrowed from my partner's wardrobe. He nodded approvingly, shut the laptop, and told me to go to his room with a swat on the backside for being a 'naughty girl'. Once there he bent me over the bed and spanked me a few times - not my thing but obviously his, and this is about both of us enjoying it - then he pulled the knickers down to mid-thigh and licked me from behind, from cock tip to ass-crack and back. He sucked my cock into his mouth from back there until it was excited enough to spring forward out of reach, then he just feasted on my asshole! I've been rimmed before a few times by females, but this guy just went to town! Up and down, round and round, and fucking me as best he could with his tongue - I almost made a mess right there and then! I'm not really a vocal lover, not known for moaning too much, but he had me gasping and moaning and whining throughout! It was incredible! He inserted several fingers at various times - I have no idea how many I was just tingling so much - but I felt pretty full so it was obviously more than one or two. Then he had me lay down on my back because my legs were going, my knees were weak, I was about to collapse on him! He continued his licking of my ass and my cock, now he had access to it again, and was inserting fingers, toys, beads, and even three pool balls at one point! He literally potted the 8 Ball in me! I was just so lost in my pleasure I lost track of what was going where, or when - it all just felt so amazingly good!

He let me recover for a while, whilst he set up his fucking machine and attached his biggest attachment - the big fat 8 inch realistic cock. He lubed it, and me (not really necessary for me, I was already a slippery mess!), set the machine at it's furthest reach, and then on all fours I backed onto it full length until its plastic balls were pressed against my own. Then he set it moving and the feeling was heavenly! We started slow but he was soon ramping up the speed, much to our pleasure - me feeling it and him seeing it disappear inside the cross-dressed Sissy Slut he had under his command and control. At this point I was on all fours, but slouched down on my elbows - kneeling in front of me he lifted my chin gently until I was back up on hands and knees and just inserted his cock into my mouth until his balls were against my chin. I closed my mouth around him and sucked and licked and swallowed as much of him as I could, LOVING being spit-roast between this Master and his machine. He gradually turned the machine up to maximum, elliciting grunts and groans from me around his cock, his fucking machine pounding my ass with a full 8" cock at 180 strokes per minute - 3 complete strokes in/out per second! I felt him tremble and he grabbed my face either side with his hands and held me there - not that he needed to - by this time this Sissy Slut was going nowhere until he was as pleasured as I had been! He grunted and jerked, and I felt his cock swell and pulse as he came in my mouth and throat and I swallowed every drop, keeping him in my mouth until he shrunk away and fell out with an audible 'plop'. The machine had gradually been stopped in the meantime and I just fell forward, sliding off the monster in my ass, collapsing on my side with a big grin on my face.

He was looking around the floor underneath where we'd been, looking puzzled - "where did you spit the cum?" he asked - "I didn't spit it! After all you've done for me it seemed rude not to swallow!" - I was proud of myself for that, and his smile made me realise he was too. We cleaned up, put the toys away, I dressed, and I left with the hope we could play again but I've not heard from him since. But I'll never forget that night of firsts!