[True story] The most amazing sex experience of my life! [FFFM] [x-post GoneWildCD] | 2016

Hi everyone, my first ever reddit post :) I really wanted to share my experience, and thought this is a place to do so. I'm sorry for any mistakes, English isn't my first language.. I realize this is a long post, and you might not be interested in reading it, but frankly I just want to get this out there. If you're not into reading such a long story, then.. don't. This a true story, I didn't make any part up, this happened a couple weeks ago.

[About me - skip if you don't want to read this] I'm chubby, a bit hairy, not the girliest of CDs, mid-early 20s.. I've been a closet CD for about ~4 years. Started out with accidentally watching shemale porn, then found the girlslikeboys series and thought it was awesome, afterwards got into more girly boys dressed up.

First time a dressed like a slut was with my step-moms hold ups, black see through top and a thong. My parents would go out of town sometimes, and I'd spend the entire day dressed that way, experimenting with anal (used cucumbers and stuff).

Later on I found a website that women used to trade/sell their clothes, most of them were new or in very good condition, so I registered as a girl and bought some skimpy clothing (too afraid to actually buy in store, and didn't want to spend a bunch of money) - 2 sexy tops, one of them came with a nice thong. Bought a cheap wig and hold ups on ebay, and a few dildos too.

Throughout this entire time I was in a relationship with my ex and soon after with my current gf. I never told anyone about me dressing up like a girl, but one time I with my ex, we were kinda on a break in our relationship and I had quite regular sex with this girl that hit on me whenever we'd meet, and she accidentally found my stash. I panicked and said that my gf forgot it. She tried an outfit on and I instantly got hard seeing a sexy girl in slutty clothes. We were a bit drunk and she though it would be funny if I'd try one of the tops. I acted reluctant, put it on and we had an amazing night, although it was regular sex (she didn't do anything to me), but it was awesome. Never thought I'd even come close to such an amazing night, but ..

[The actual story] My gf was getting ready for a girls night out. One of her friends came by to our place so they could go together and meet up another friend later on. My gf is super sexy and her friend comes a really close second. They weren't dressed slutty or anything, but when 2 fit girls dress up tight it's hard to ignore the sight :) They hanged around and then left. It was already ~9pm and I was told they'd come back at midnight back to our place for some reason. Basically I had ~2-3 hours of alone time and was very horny seeing them go out, so I got my stash and thought I'd play around for an hour or so dressed up with my dildo.

Hit the shower, shaved my ass a bit, got cleaned up and ready to go. Put on a sexy black thong, as I was sliding the hold ups I was already getting aroused, snapped the garter belt on for added slutyness, squeezed myself in a sexy black top/dress and put my wig on. Got lubed up, put on porn on the TV (a girl getting gangbanged). Started to jerk myself slowly (when I'm that horny and feel slutty I cum really fast, sometimes when I'm not even fully erect yet). Positioned myself on top of my dildo, slid my thong to a side and started to slide my way down. I don't have that much anal experience, so I always struggle at first, and still can't manage to get the dildo fully inside me.. But I was enjoying it, slowly riding the dildo, not really touching my penis as I felt I'd just burst if I touched it, watching a girl get gangbanged through all holes on my TV. I felt so slutty, and wishing I was riding a real cock (I do want a guy to bang me, but can't find a normal guy..).

I then attached the dido to the wall and got down on my knees like a slut and giving the dildo the time of it's life. I wasn't erect but super horny, I started to touch myself so I'd get hard but it felt like I was about to cum. The hair from my wig was getting in my face, felt like a real girl getting banged and wishing someone was pulling my hair back. I got erect really fast and started jerking off, feeling like I can last at least a few minutes. But watching a girl getting banged rough and banging my ass with the dildo was just too much, I didn't want to cum that fast.

I sat down on the sofa facing the TV, spread my legs and put them in the air, started sliding the dildo in and out slowly. As I got even more horny I started going faster and faster, the porn started getting more intense as well, I wasn't jerking off as I'd cum just from touching it, and it wasn't easy banging myself with the dildo and jerking off at the same time. The hair from my wig was in my face, I was hot and sweaty, my ass really loosened up and getting more and more deep with the dildo. I joined my legs and held them up in front of me, banging my ass as fast as I could. I knew that I couldn't last like this any longer and needed to cum, but everything felt so good so I decided to bang myself a little more, then jerk off and clean up. I increased the volume on the TV, closed my eyes and imagined that I was that girl.

I felt a breeze go by, and when I opened my eyes, to my shock I see my gf and 2 of her girlfriends just standing there in disbelief. Apparently everywhere they went the places were full and they decided to just come back to our place and hang out. Our front door opens up right into the living room and they're just standing there not knowing what do to. I'm on the sofa, dressed like a total slut, my legs up in the air and a dildo in my ass, with rough porn blaring from the TV. I'm guessing they where more shocked than I was, but I just wanted to die right then and there. I was so embarrassed, I had no idea what to do, I slid the dildo out of my ass, holding it in my hand, feeling even worse. One of the friends asked my gf if they should go, but she couldn't say a word, just staring at me also embarrassed that her friends are seeing her boyfriend like that. I really didn't know what to do. I said I'm really sorry, switched off the porn, and ran to the bathroom.

My body was trembling, I was panicking, I felt so ashamed and in total loss. I could hear the girls whispering, I wanted to rip my clothes off, and I remembered I left the dildo in the living room making me feel even worse, when someone knocked on the bathroom door. It was my gf and wanted to come in. I didn't know if I should or not, but I did let her in. She closed the door behind her, and was just staring at me - fully dressed like a slut with lube coming out of my ass and down my hold ups. She started to say something but couldn't get any words out. I grabbed a bathrobe and put it on so she couldn't see me like that, but the stockings and wig were still visible to her. Her first question was if I'd been doing this stuff for a long time. I said yes.. She asked where I got the clothes and I said I bought them online. Then she just stared at me for what felt like eternity. I could hear her friends whispering in our living room. I didn't know what to do, so I decided to take off my clothes, but my gf stopped me. She asked if I could take off my robe so she could see what I look like. I wasn't sure what to do, everything felt so bad, but I took my robe off. She was checking me out, looking at me with a judgemental glare. "So you're a whore then?" she said. I didn't know how to respond so I just nodded.

She kept looking at me, and then touched my dick! I was so shocked, I couldn't figure out if this was sexual or not. My gf is conservative in the sack - I rarely get a bj, she doesn't like cum, only sometimes does she want me lick her pussy and almost never starts fooling around, I always have to start. So I didn't know how to react at all. She took my dick in her hand and didn't really stroke it but kept fondling it. I wasn't getting erect but I wasn't sure if that was her goal. As she was fondling me, she was still checking me out and for some reason I felt even worse. She told me to come with her and as she was holding my dick she started to lead me out of the bathroom to which I jumped back and said no way, I'm not going out there like this! She calmly said to just do it. Inside I was just falling apart, I really didn't want anyone to see me like this, but I just let go and gave in hoping this will all end soon.

She went first and I followed, when we came into the living room her 2 friends where sitting on the sofa where I was just fucking myself with the dildo, looking at me with a O.O stare. My gf just stood there and 3 girls where staring at me. I didn't know what to do and I sat down an a couch, I didn't want them seeing my dick and the thong is really tight so it doesn't help concealing anything, so I squeezed my legs together tight like a girl. I couldn't understand why my gf brought me out, why she was doing this, all that was floating through my mind is that our relationship is probably over and this is just to humiliate me. Her friends where looking at me, I could smell a bit of alcohol in the air, they got a few drinks at a bar while waiting for a table, but decided to bail because of the noise there. One of her friends is really bold and straightforward, and she just said "Well I didn't know that you were a slut, do you like fucking that dildo?". I immediately started blushing and panicking even more, again I didn't know how to respond so I just nodded. She chuckled at the sight me blushing and said "ha I've never seen a shy slut before" and they all giggled. They started to smile and recover from the shock I guess, and started teasing me a bit with questions like do I suck the dildo, do I fantasize about a real dick, would I like to be fucked by a guy. My only answer was a quite yes or a nod. My gf was silent and still standing throughout, but responding to my answers with chuckles.

The girls started to shift their legs and kept crossing them, I figured they where getting a bit horny or something, but I was just too humiliated and embarrassed to react to that. The bold friend asked if I could stand up so she could have a better look at me, and I felt even worse knowing that they will actually be checking me out and judging me so I was reluctant and didn't stand up at first, but the other friend started chipping in and it felt like they where honestly curious and weren't trying to make me feel bad or anything, and I slowly got up and just stood there trying to cover my dick as the thong was barely covering it up. They where smiling and checking me out, gazing at me. The bold friend picked up my dildo and made a remark that she's never seen an actual dick that big and was greeted with a round of chuckles from the girls. She said something about about the fact that I was fucking myself with a dildo that size, and it sounded almost like a compliment or something, but my mind was just all over the place and I almost felt like I was blacking out. She then extended her arm at me holding the dildo wanting me to take it. I was lost for a moment but took it, while trying to hide my dick as well as I could with the other hand, but I realized that I was doing a bad job at it and they could see pretty much everything anyway which made me feel ever worse.

So I was standing in my living room, dressed like a complete whore, with a slippery dildo in my hand in front of my gf and 2 of her friends. I thought fuck this, and started tried to walk out of the room when my gf stood in front of my path and asking why I was leaving. I said this is too much, I feel really bad and ashamed. To my surprise the girls warmly said that everything was OK and that they aren't judging me or anything, they're just curious because they've never seen a guy dress like a girl before (skipping the part of them having seen me fuck myself with a dildo..) and asked if I could stay and talk to them about it. I was really torn, I guess if I wasn't dressed that way or them having watched me blast myself with that dildo - given the right circumstances I could probably talk a bit about it, but not like this. Yet they seemed sincere and nice about it, I started to calm down a bit, but still in shock and disbelief. I sat down and glanced at the girls. My gf was still standing there, the 2 girls where still on the couch, but it was only then did I notice how hot all of them were. My gf was in super tight jeans with an even tighter top. The bold friend was dressed similarly, but wasn't as hot as my gf. The other one was in an EXTREMELY tight dress that ended above her knees, also some kind of nylons either stockings or pantyhose and she had to keep her legs really tightly closed together for her panties to be not visible. All of them where really sexy, make up, tight clothes, and I felt a little tingle, I was getting a bit horny. And then the girl in the skirt crossed one of her legs on the other, and I could clearly make out that she was wearing hold ups/stockings and not pantyhose. I actually felt my erection coming back and panicked. I was squeezing my legs together tightly, and also placed the dildo onto my lap so if I did get a hard on it wouldn't be visible. It was the strangest feeling - I was shocked yet horny.

.. continued in the comments ..