A quick story of something Dave and I did for fun one night.
Dave and I had a secret relationship that my wife didn’t know about despite me bringing Dave around a couple times and introducing her to him. She kept asking about where I was going and eventually I just told her I met a new friend thru doing my side hustle as a handyman and Dave and I got along because we liked sports and stuff. My wife paid such little attention to me and the things I like that it was easy to get away with keeping things from her.
About 6 months into Dave and I screwing around together, him as a tall handsome man with a man’s man mustache and dark hair with a sexy patch of equally dark chest hair lightly covering his toned chest and stomach. And me, his cross dressing bottom that had become so enamored with him, I would do anything for him. (For those who needed a reminder or it’s your first time reading my story.)
We were a couple. We’d go out to dinner and drinks together. We went to movies together, and we’d go to parties together with his friends. I was always dressed as a woman. A woman that I called Samantha and it drove me wild when he’d introduce me as Samantha. We’d always end the night/date with incredible sex. I lived for my nights with Dave and despite identifying as a straight male for 42 years, I had no quarrels with dressing as a woman for him and giving him the best sex life I could.
Dave was not rich by he did have a very well paying career and over our time together, he has assembled an incredible wardrobe for me. Dresses, lingerie, high heels, underwear, even relaxing comfortable pajama type stuff I will wear when we watch movies together on his couch.
As I said, I live to please him and I can’t think of a better way to spend my time. The feeling I get when his cock is inside me and I can feel his pulse beating as my ass squeezes his shaft and we lock eyes is intoxicating! As I feel him explode inside me. His cum hitting the walls of my anus and knowing that I made him cum like that.. well, it’s addicting to say the least. There’s no question that Dave and I were in love now.
One night at dinner Dave asked me what I wanted for my birthday and since I didn’t have an answer right off the top of my head, I jokingly said I wanted another guy to join us some night, which was absolutely true but because these strange emotions between us had manifested, I certainly didn’t think we’d ever take that step. Dave chuckled when I said it but didn’t respond beyond that and I thought that was the end of it.
A week later I was able to get out of the house and Dave was going to take me away for the weekend. I told my wife we were going fishing and she bought it. Dave and I drove up to this cabin about 3 hours north of us where we’d spend the next 48 hours. I’d also like to add that on that drive, I sucked his cock while he drove. It wasn’t a planned thing I just got really horny on the drive thinking about being with him all weekend and told him to take his cock out.
The cabin was incredible! It had all modern amenities including Wi-Fi so we didn’t feel like we were roughing it by any means but it was in the woods and it was secluded. Dave handed me a present after he made us dinner and it was a new outfit and bra and panties with a garter belt and stockings. Ever since we had met, I had been growing my hair long and trying to lose some weight so I could have a more girlish figure and I immediately thought the dress was too small but when I put it on I was blown away I could fit into it! I was starting to look more and more like I wanted!
After I tried the entire outfit on Dave and I had incredible sex on the couch. We followed it up by watching a movie and retreating to the bedroom and having more sex.
The following day we just roamed about the woods on hiking trails and we rented some bikes and had a nice day out in the great outdoors. At one point on the hiking trail, we walked off trail about 50 feet and sucked each others cocks.
That night we had dinner again and did some small packing since we were leaving in the morning. Dave wanted me to wear the little black dress he bought me, and the black silk bra, panties and stockings he got for me. I loved the entire thing so I absolutely wore them to dinner.
After dinner, there was a sudden knock on our cabin door. I was startled not expecting anyone way out in the woods but Dave casually walked to the door and opened it. In stepped a man. He was similarly built to Dave but had light brown hair and no facial hair. He had piercing blue eyes and a nice smile.
“Who is this?” I asked
“Your birthday present. You said you wanted a guy to join us, so I asked my friend Mark to come up tonight. Is that ok?” Dave explained
“Of course!” I said trying not to sound too excited but I was ready to bounce off the walls.
My heart pounded as Dave reached out and grabbed my hand standing me up. He wrapped one arm around my waist and Mark approached me on my other side and did the same. I’ve never been the kind of guy that wears cologne or anything like that but when it was on these two gorgeous men, it drove me nuts!
Dave leaned in and kissed me the way he does now, passionate and full of tongue. As soon as he stopped Mark leaned in and kissed me the same way. The emotion wasn’t behind it like Dave’s kiss but the energy was there and I knew I was about to have some fun!
After a few minutes of the 3 of us making out and even watching Dave and Mark kiss a few times, I took their hands and lead them to the bedroom. We resumed our kissing and Dave helped me remove my dress. Both of them began groping and kissing me all over. Dave had his face buried in my neck kissing and nibbling while Mark and I were full on making out. Dave’s hand was already inside my panties softly stroking my cock and Mark was pinching and playing with my nipples.
When I couldn’t take it anymore, I sat on the edge of the bed and unbuttoned both of their pants. Both of them dropped their pants and underwear to the floor and kicked them aside. I instantly grabbed a cock with each hand and began stroking them both. I put Dave’s 9” in my mouth first and stared slobbering all over him. They both had now removed their shirts as well and as I spit Dave’s cock out to switch to Mark’s which was about 7” but thick, I noticed the two of them making out and playing with each other’s nipples. It turned me on even more as I opened my mouth and shoved Mark’s dick inside. I got him nice and wet!
Dave then pushed me onto my back and pulled my panties down and got on the bed next to me. Mark lifted my legs up and started licking my asshole! Holy shit! Holy shit! Holy fucking shit! Dave had never done that to me so I didn’t know how insanely amazing it felt! Mark held my legs spread while he tossed my salad and Dave got on top of me in a 69 position and we sucked each other off. I now knew I wanted Dave to add licking my ass to our routine so I started licking his asshole in hopes he’d see how incredible it felt and add it to our regular rotation. It didn’t work at first but Dave eventually came around a few months down the road! Goddamn I’m glad he did!!!
Because Dave was still on top of me I couldn’t see Mark had gotten up and was positioning himself to enter me. Suddenly I felt Mark press the tip of his cock against my hole and push. He wasn’t as gentle as Dave was with this but I was much more comfortable with it and didn’t bother me. I felt the tip of his cock slip inside me and my eyes rolled back in my head and I forgot all about Dave’s cock, balls and asshole right in my face.
Dave sat up and got on his knees in front of my face so I could continue to suck him off, while Mark was full on fucking my ass now. After a minute or so I pushed Mark out of me and told Dave to reposition himself. I got on all fours and began sucking Dave’s cock again. Mark put his cock back inside my ass and resumed fucking me. My fantasy was coming true as two men were now spit roasting me! I remember thinking, if only there were two more guys so I could be jacking them off with my hands.
I felt Mark’s grip on my hips tighten more and more and his thrusts began to get harder and deeper. I moaned out in ecstasy but with Dave’s dick hitting the back of my throat you probably couldn’t hear how much I loved it! Just then Mark stopped and let out a loud grunt. I felt his cock pumping spurt and spurt of cum out and tickle the inside of my ass.
“Your turn.” Mark said to Dave while trying to catch his breath.
Dave climbed off the bed and positioned himself behind me. I could feel Mark’s cum dripping down my thigh and I thought I hope I look like a slut right now! Dave spit a big glob of saliva on my ass, not that he needed to, and pressed his dick inside! I moaned out again as he went as far as he could on his first thrust. Mark got on the bed and sat down in front of me. His cock was staring me right in the face as I put my head down. He was still trickling drops of cum from his semi hard dong and since I was wanting to look like a slut in that moment, I just put his cock in my mouth. It tasted amazing! Sweat, saliva, cum and ass apparently get me going!
While I sucked the last droplets of cum from Mark’s cock I could feel Dave back there rearranging my gut. It felt like his cock had grown 5 inches and was all the way in my chest. One thing that always turns me on is when Dave fucks me in a missionary position and I can see his cock pressing against my stomach sliding in and out. The more weight I lost for him the more prominent his cock looked inside my gut.
Shortly after I felt the same thing with Dave as I felt with Mark. His grip tightened on my hips and his thrusts became more intense. I knew he was about to cum! I still had Marks cock in my mouth and I had started stroking my own cock as well when I felt Dave clinch up and scream.
“Oh my fucking god!!!” He yelled very loudly “oh god it won’t stop!” He added as pump after pump of cum shot deep into my ass. I had shot my cum all over my hand and was licking my fingers as Dave held me in place. As he finally let go and slid his cock out of my ass, I felt what seemed like a waterfall of cum drain out of my hole and down my balls and legs. I reached down and swiped some up with my hands thinking to myself, there’s cum from 2 men draining from my ass right now! I’m a fucking whore tonight! I licked the cum off my fingers and we eventually all collapsed on the bed in a hot sweaty mess. No doubt the room smelled of sweat and ass but it wasn’t bothering us.
The cabin had an open shower. It was pretty big and didn’t have a door or curtain on it, just a small wall at the bottom to keep water in the shower. It was definitely big enough for two people as Dave and I showered together that morning while exchanging hand jobs. As we lay there, Dave suggested we try to all take a shower together. I loved the idea and as Dave and I stood up and I removed the rest of my underwear I never got around to taking off, Mark joined us in the bathroom a few seconds later. Dave started the water and as Mark got in, we were very surprised that all three of us fit in quite nicely. Snug but comfortable. I mean we weren’t taking a shower together to not be rubbing against each other right?
I started off by soaping them both up and running my hands all over their bodies periodically kissing them and even fondling their cocks and ass. Once they were clean and rinsed off, Dave told me to get on my knees. Both of them were hard as a rock again so I knew I had to take care of them. Before I could get started, Dave started pissing on me. I know it’s a bit weird and I wouldn’t do it unless I was in the shower but I like when he pisses on me. Mark was a bit shocked at first but began pissing in my mouth before Dave finished. Again, it’s kind of weird but two guys that just fucked my brains out were now pissing in my mouth. Not a fantasy I had going into this crossdressing phase but nonetheless a great one!
As they both wrapped up peeing on me, I began sucking them both off. We stayed in that shower for almost 45 minutes as I sucked them and then they both finished themselves off on my face and chest!
When I jokingly told Dave that I wanted another guy to join us some night I was serious and it was because I wanted to be treated like a slut for one night. I wanted Dave to put aside any emotional attachment to me or feeling he had and just him and another guy just fuck me and treat me like a slut. I got exactly what I wanted. I got it again the next morning before we left and I got it again as we got back to Dave’s house. I can’t believe how good it feels to be a little whore sometimes. Especially when you see how much it makes your man feel good! I know Dave has strong feelings for me and he’s even used the words I love you to me, but seeing how relaxed he was on that drive home made my weekend! I think he noticed how much I enjoyed being a whore and chafing up any kind of routine we had begun to fall into.
Mark has joined us a few times since this night, and will continue to do so. Eventually we will work our way up to 2 more men joining us. I want to have as many men cumming and pissing on me as I can! 4 sounds like a great night! When it happens, I’ll definitely write about it!
Thinking back on this night, which was about a year ago, I have these weird tingly feelings all through my body. Being a whore once in a while is exhilarating and intoxicating. Having two different men hold you down and pump their hot cum in your ass all night is the bees knees!
👄This will be the best oral sex you have ever experienced.👅