So a little background first. Me and my gf have been going out for a year and a half. Just before our 1 year anniversary i confided in her that I enjoyed crossdressing, which for me was a huge deal since I had never come out to any one before. It’s been 7 months since then. Now on to the juicy part. So yesterday I got in full dress. Makeup, wig, collard shirt and a school girl skirt (not too small we had guests coming over) I cleaned the house and when our friends arrived we played some table games for a few hours then they left. Me and my gf were sitting in the couch together when she turned and said. “You want to do it?” I excitedly got up and darted to the bedroom to change into my skin tight, see-through pink babydoll. As I was fixing my boobs in the mirror she hopped in bed and started fingering herself under the covers. When I came into the bedroom I climbed over her slowly and gave her a long kiss licking her tongue. She pushed me back and threw the covers off of herself and then grabbed my head and shoved it between her legs where I began licking and rubbing her till she was good and wet. Her hands all the while pressing my face deeper into her. Her moans and twitches got me so hot I pulled back and got into postion. She rubbed the top of my rod against her, spreading her juices over it. Then lined it up and pulled my hips into hers. She always moans loudly at the first penetration. I grinded against her hips making sure I was pressed firmly against her clit, and after a few minutes she exploded with a loud scream. I kept grinding till her orgasm was finished, and then she said. “My turn.” I got off of her and reached off the bed into our drawer of toys and pulled out her medium sized purple strapon. She slid it into place and i helped her tighten the straps till it was firm against her body. She knelt down on the bed over me and grabbed my head forcing my mouth over her purple dildo till it was deep down my throat. She held me in place there till I started to gag and then she pulled it back slightly before gently thrusting it in and out of my mouth. A few times she would push my head down farther telling me to take the whole thing. I’m not very practiced at this yet but I try my best which isn’t very good but she forces me to take more and i gag again. She pulled my head back off and strokes her dildo with her hand to spread my saliva over it while telling me to turn around. So there I am, bent over on all fours and she forces my knees apart, I feel her wet finger slid down my ass lubing me up for her cock. Then I feel her rub the tip against my tight hole and a great pressure as she starts to press it into me with her hips. I reached a hand back and pulled my cheek apart which helps her get the tip inside of me. Then she thrusts hard forcing it in and i couldn’t help but stifle a scream into a whimper as it filled me up. I could feel her hips against me. She was balls deep inside and she let it sit there for a moment enjoying my whimpers of pain, then she began to ride me. Slowly at first, but increasing in speed and depth with every thrust. All the while I was moaning and grabbing at the sheets. Then she did something new. She reach around me and pulled me back up on top of her. She held me up by placing both her hands over my breasts and kept thrusting as hard and deep as she could. It hurt, but in a good way. I started to rub myself and after a few seconds I exploded and she pushed me back down onto all fours pressing her dick into me as deep as she could till my orgasm was over. As a cross dresser it feels amazing when im treated as a girl. But this connection is on another level. To be treated like a girl by my gf. <3 simply orgasmic.
Category: gonewildstories
My last day on the job… [MF]
It was my last day at my previous job and my supervisor walked me out of the building (it’s their policy). She walked with my all the way to my car, which was not surprising because she was one of the nicest people I worked with. I thought she was just being extra nice, but when we got to my car, I opened my door and she asked if she could come inside for a second to discuss something private.
She got in and asked what size sausage I have. (I worked in the meat department where that is not that unusual of a question). I was confused why she was asking me this outside of work, so I just looked at her. I asked her, “What do you mean?” She gently grazed my crotch with her hand and repeated the question, “what size sausage do you have?” we smiled at each other and she said that she was always curious. I instantly became extremely nervous to the point where I couldn’t even find the words to say. She continued to caress my crotch, and asked if I was going to show her. I told her that I would be happy to show her, but not in the parking lot. We decided to move to the back of the parking lot where there are not so many people. So I drove to the back and parked where nobody could see us.
She told me that she would regularly check me out at work and has even noticed my bulge a few times and it made her curious and turned her on. I think she was just flirting with me because I wore an apron 90% of the time, but this was a huge surprise to me because I know that she is married and has two kids. She is probably nearly twice my age.
She started to undo my belt and unbutton my pants. She reached her hand into my pants and grabbed my soft dick. Her hand was super cold, but I got used to it quickly. She massaged my dick and gently squeezed my balls until I was fully erect; which took a total of 1.85 seconds… (I was worried that I wouldn’t be able to get hard because I was so nervous, but that was not at all the case) I pulled my pants down past my knees which fully exposed my erection she smiled with my dick in her hand and said, “Perfect size!” She turned her body and got up on the seat so that she was in a position where she could use both hands, and eventually her mouth.
Stroking my hard cock slowly, she simply observed it and gave me some complements about it. She liked the shape of it and how the tip inflated it got when I became fully erect. She squeezed it and some precum dripped out. Her tongue was sooo soft as she licked up the drop as it ran down the shaft of my cock. Then she proceeded to put the tip of my cock in her mouth. She used her tongue again to wet the entire tip and then sucked hard making a loud “slurping” sound with a nice “pop” at the end.
Meanwhile, I’m just sitting there, completely blown away (pun intended) and shocked that this is happening. I am EXTREMELY nervous and excited at the same time.
I didn’t know what to do with my hands (lol) so I just put my hand on her shoulder. She responded by pulling her pants down a bit and directing my hand to her pussy from around her thigh. Her pussy was very wet! I was surprised by how turned on she must have been. It was also very soft and warm. (If anyone would have walked by my passenger side window, they would have gotten a full view of her pussy and asshole bent over from behind!)
It started to become obvious that she has done this before. Who knows how many times? Not only did she seem extremely comfortable sucking my dick in a parking lot, but she also played it out perfectly so that she could get away with it so that nobody would know. I was completely shocked that the sweet woman at the grocery store, who has a husband and kids, is actually very very naughty!
I slid a couple of fingers inside her and they went in easier than I expected. I slid them in and out until my fingers were completely covered in grool. I rubbed her pussy and slid them back in. She paused for a bit to enjoy the pleasure and let out a deep yet feminine moan. She grabbed my balls harder this time, pulling them down and she started to deep throat my cock. I have never been deep throated before, so this caught me completely off guard. I was about ready to explode at this point, so I stopped touching her pussy and she gagged a little bit as she pulled my dick out of her mouth.
She looked at me and smiled again. Then she grabbed my hand and sucked her pussy juices off of my fingers and then said, “ya know there’s two holes back there, right?” I nervously laughed and she went back to sucking and stroking.
I have never done anything anal before, so having no idea what to do, I felt around for her asshole, and slowly pushed a finger in. I could feel her ass tighten around my finger and then it would relax, and then I pushed in a little further, and it tightened again. I pushed my middle finger in and out as her asshole was tightening and relaxing, but only a couple of times because I reached the point where I knew that I needed to cum and there was no going back.
I told her that I was going to cum and she started sucking and stroking at the same time faster than ever! She probably only stroked like 3-4 times before I exploded in her mouth. She wrapped her lips around the tip and sucked the cum right out of my cock. It was the most intense orgasm I have ever experienced. Unable to do anything other than grab her left butt-cheek, I released my entire load into her mouth.
She sat back down in the seat, licked her lips, and swallowed. She told me that it was a big load, and I awkwardly said thank you. My dick was still twitching so I just grabbed onto it. She touched herself a little bit and we made eye contact and giggled a little bit. Then to make it more awkward, when I pulled my pants up I accidently hit the gas, which made my engine rev loudly.
As she pulled her pants back up she told me that it was an honor to work with me and she wished me good luck in my future career. She looked in the mirror and fixed herself up while I just sat there in complete bliss. I drove her back to the door because I’m a gentleman (lol) and hated for her to walk all the way through the parking lot.
She got out, wished me good luck one more time, and I checked out her ass as she walked back into the store. I could tell that there was a little perk in her step and she seemed happy/proud of herself.
So[M]e date night [F]un
Here is the story of Thomas (22M) and Isabelle (21F). Both of us are university students, athletes, nerds, and sexual deviants. I am roughly 5’11”, 155lbs, build of a runner, while she is 5’7”, 140lbs, build of a swimmer, with nice strong muscles and a delightful smile. She has nice shapely hips, a cute, firm ass, and a pair of nice C cup breasts. I have been blessed with nice long cock that my partner was amused to note as being as thick as her wrist, along with some defined abs and a good butt we make up what we imagine to be a pretty good looking pair.
We had been seeing each other for a while and had decided that a nice dinner date was in order. In addition to providing me with a chance to treat her well (as opposed to treating her like a naughty little deviant like I normally did), we figured there would be more than a few chances for the two of us to get up to all manner of mutually pleasurable mischief.
The best way to end an argument [FM]
So my husband and I had exchanged nothing but civilities for 48 hours. He was annoyed about…well, I’m not really sure what he was annoyed about, but I was bored of it and also very, very horny.
I’d just ran myself a bath && he mentioned something about ordering trainers online. Things were starting to thaw apparently so I took a shot. As I was pottering about I sent him a link to a most delicious looking (mild) bondage set and told him if he was ordering stuff anyway then he can get this for me. I heard the ping of the text and about 3 and a half seconds later he was standing in front of me.
I tried to look surprised, to look innocent, but it had been 5 days, I can only hold out so long. Next thing I know I’m being dragged to the bedroom, conveniently naked prior to my now forgotten bath. I laughed as he threw me on the bed and stood next to it, taking off his shorts, tshirt already on the floor.
[F] Masturbating in the train
I’m sitting on a boring train right now, minutes from making myself cum so hard in my seat. The train was packed as usual with tons of college students heading back to campus. Nearly every seat was taken but I managed to find an empty window seat. I plop down and get ready to relax, putting on my favorite playlist. This random guy asks me if the seat next to me was taken and I said no. He was average looking, on the skinnier side but seemed cool. I was wearing a black sweater and navy leggings.
I dozed off listening to some of my fav songs but was woken up to this guy’s leg splayed and pressed against mine. He was fast asleep, mouth hanging open slightly, headphones plugged in. I let myself take note of him, the way his jeans fit him, the slight bulge that made me think naughty thoughts. I briefly thought about what his cock would look like, what it would feel like stiffening in my palm if I started to rub him slowly. I felt my pussy responding to these thoughts. I texted a guy that I mess around with a lot and we agreed to meet later once I got back to campus. I started browsing r/gonewildaudio as usual, my fav for when I want to tease myself in public and eventually get off.
Selling Real Estate [MF]
I had just moved to a small town a couple of years after graduating from college for work. For a small town though, it had a phenomenal number of real estates trying to sell or rent out properties. The reason for this, was the town had a seasonal population due to a university campus located there. There were advantages and disadvantages with having so many real estates in a town of 60,000 people. The advantages were the abundance of homes for rent and the low rentals. The disadvantages were that by shopping around was that it inevitably took longer to find a perfect place. After checking out about 5 agencies, I saw this apartment that looked ideal. I rang the agent for an inspection, but their policy was for supervised visits only.
Banging my Boyfriend and my Ex in the Same Night [MF]
I had been dating D long distance during grad school and would come home to stay with him during long weekends and holidays. One night while back in the city, I received a message from T, my former college boyfriend. He was moving to San Diego in two days and wanted to get together for drinks before he left the East Coast. We were on friendly terms but I hadn’t seen him in almost two years. After some hesitation, I decided to go, we were both in relationships so I figured we wouldn’t get into too much trouble.
We met up at his apartment. His girlfriend had already left for California and T stayed behind to wrap up some loose ends. A professional musician, T still hadn’t packed up any of his instruments. I sat down at his keyboard and starting mindlessly playing while we caught up on what was going on in our lives. T asked if I remembered some of the old songs we used to play together. Our plans to get drinks at a local bar were quickly abandoned as we spent the next few hours making up lyrics, drinking up the rest of T’s wine stash, and jamming out.
Finishing unfinished business [MF]
A little background, when I was 13 this girl named Lynn was into me in middle school but she had a boyfriend but I wasn’t into her. One day my teenage hormones got the best of me & we met up in the locker room & made out, could’ve gotten farther then that but I got scared & walked out. Fast forward 10 years & we found each other just out & about & we exchanged numbers & started texting. One day our texts started innocent & then turned sexual, ‘when you gonna be my way?’ Her replay ‘I’m actually down here, my boyfriend is sick so we came to the hospital’ ‘oh I’ll come see you then’ ‘ok’.. I live about 5 minutes from the hospital & when I got there, we started talking & I asked her ‘when you gonna give me some?’ She said ‘I wanted too while he was getting seen by the doc but the security guard keeps following me’ I said ‘meet me at this certain part in the hospital at a bathroom cause there is no cameras & when you go in there, leave the door unlocked, take your panties off & I’ll walk in cause I’m not wearing underwear.’ One minute after she walked away from me, I entered the bathroom & there she was ready for me. I made her bent over the sink, took off my pants & entered into her, she was tight, hot & so wet that I just slide right in. I pounded 10 years of sexual frustration into her, skins slapping, sweat building, her small handful booty jiggling as my cock plows into her & her biting into her arm so she doesn’t moan out loud & get us caught. Her pussy got so wet I slid out a few times, I sat on the toilet & told her to ride me, when she sat on it, I felt her muscles just grip my cock & as she is going up & down on me, I pulled open her shirt & sucked on her B cup titties, it didn’t take too long for me to come inside her, I forgot I wasn’t wearing a condom. When we got out she went one way & I went the other, & that was the day we finished what we started in the bathroom in MS & also the day we started a year & a half long affair with each other
[FM] I moved into a new neigborhood 8 months ago and I’ve done it with two guys in my cul-de-sac already
[Posted this in confessions and was told by someone gonewildstories would love this put here!]
Life’s boring here in the suburbs. Unbearably boring, but I was transferred here in this shit city for work so I guess I’ll call it home for now.
[MF] Cheating for a big one (I really, honestly couldnt help it)
This one happened a long time ago. Anyone who reads my post history will know that I’m usually into power play dynamics; mostly femdom and some femsub stuff.
My boyfriend at the time was a shy 16 year old who also enjoyed this kind of thing. We had a nice time playing with each other and exploring each others bodies.
But then there was Devon. He was tall, confident, a bit too loud for his own good, and he started messaging me on Facebook, and was always just a bit flirty.
In time, I was hanging out with him after school, and I’m not going to lie, I found him pretty attractive. Not “leave my boyfriend” attractive but… Definitely “ok, can you please fuck me now” attractive in an animal sort of way.
I always found my eyes drawn to his hands, imaging what he could do to me, and… Well.. his bulge.
It was big. I honestly thought he was stuffing it, it was that *apparent*.
One night I went to Devon’s house after school. And he offered me a drink. I knew what that would lead to.