Never did I imagine that I would be on my back, legs in the air, meeting the thrust of a man willingly as he pumped into me vigorously while in a dress, wig, and boots.
I consider myself bi but have never been open to anyone about it. Typically I date woman but when single and in dry spells I have seeked the companionship of a man from time to time. I found myself in my early 20s to love to please men orally. Most of my encounters up to this point were single hook ups, with the exception being a couple of guys that I would please until they got into steady relationships. I did get curious enough once in my mid 20's where I did try to bottom but it wasn't anything thrilling for me and completely avoided until the present now in my early 40s.
This all started with a grindr hookup. I had posted myself as a chubby guy who enjoyed pleasing men orally. Steve messaged me and he met all my requirements, older, lived alone, in a house not in a neighborhood. We did a bit of chit chat but after about 15 minutes I was on my way to his house.
As I drove up into his drive way he texted me the front door was opened and that I could meet him in the living room. When I stepped in all I could think was that this was a bachelors paradise. Pool table, beer fridge, and a large tv mounted up with a basketball game on. Then I turned to the couch and saw Steve. Just as in his pictures 6'2", pepper hair, muscular arms with a nice dad bod, already naked and stroking his cock.
I figured we might as well get down to business. I took off my shirt and knelt before him as we locked eyes and said "hi". I started to tease him while stroking his cock while I asked him what he liked. He wanted it sloppy, slow, and with plenty of deep throat. I told him that he was free to push me down, talk dirty, and be a bit rough but nothing that would leave a mark. Finally I asked him to warn me when he was going to cum.
Stopping the eye contract, I looked down to his member that I was stroking with in my hand. He was bigger than average, maybe 7". Kept stroking him as I noticed his big red mushroom head and larger than normal balls. I was mesmerized and zoned out for a moment when I heard "stop staring at it and suck it". I lowered myself to him and gave it a kiss, took him in my mouth and proceeded to give a slow blowjob where I just lost myself in his hardness. He got his wish as proceed to give the sloppiest head I'd ever given. After about ten minutes started to deep throat him. He started to push me down, getting my nose to his pubes, my chin to his balls, and started to ask " you like that slut?". And the only thing I could do was shake my head yes and left out a moan of enjoyment. I needed to catch my breath so I came up for a minute and got back into a stroking rhythm. I was so turned on and submissive in the moment. I told him how impressed I was by how hard and big he was. How much I loved his cock in my mouth and how I loved to feel my lips around his cock. Steve responded by pushing my head down to his cock. I was so turned on by the way he wasn't afraid to handle me. I got back into it and after a few minutes, I got a tap on my shoulder, heard his grunt, and as I moved my lips from his cock as it busted and got a shot of cum all over the left side of my face.
Steve was breathing heavily, but he managed to tell me how good a job I did. I got up, excused myself to the restroom and cleaned up. When I came out I figured I'd grab my shirt and have the awkward bye never to be seen again. However Steve started a conversation. He asked if I was Gay, did I have a partner, and I would be interested in having another encounter. I told him I considered myself Bi, was single, and would consider doing this again and provided him with my phone number. He offered me a shot of whiskey which I accepted, and I left.
A few days passed, and the encounter with Steve stayed in my mind. His size, the rhythm we got into, the way he talked and handled me, all got me excited. Usually post nut clarity fixes all of this but there was something about this experience that was hot and a lot of fun that had me reliving the moment in my mind each day. Luckily on the 5th day Steve messaged me and wanted a second encounter.
We worked out a time for later in the evening of the same day. The second encounter was just as good as the first, and next thing you know it became a regular thing for us. After a few encounters later, Steve inquired about anal and I explained that I had tried it once but it wasn't for me. He then asked about me swallowing his load. I told him I would need an std panel test and that I would need something in return. Steve all eagerly pulled out his phone. He had just gotten his physical which included all major STD testing which were all negative.
He then looked at me and asked what I would want in return? I didn't quite know what to say, I thought I would get more time to think about this but now I was on the spot. I looked at him and told him that I "always wanted to crossdress". Did I really blurt that out loud? It wasn't a lie but also something that I wasn't quite ready to share with anyone, much less the guy I've been blowing a couple of times a week for the last month.
Steve's face just lit up and said "absolutely". I wasn't quite sure how this happened but Steve was really excited and was already on a shopping website and told me to go wild and order what I wanted, on him. Crossdressing was how I got into all this. In my early 20s I really got into blowjob porn and I went from pretending to be getting the blow job to wanting to give it. The curiosity of giving a blow job got the best of me one night and that's how I started my journey into intimacy with men. I loved the submissive role and found it a great way to get away from it all when focusing on pleasing a guy. I'm a big masculine guy though, while the thought of crossdressing had always crossed my mind, I figured I would never look feminine so I never explored it. Now here I was with a guy who not only was willing but excited to do this with me, and all I had to do was order some items off the web.
I looked down at Steve's phone as he sat next to me and said "you know what you're getting princess?". I rolled my eyes as I knew I was not going to stop hearing things like that moving forward, but was excited to get started. By the end of the night I had a few pairs of bras, panties, dresses, and nylons on their way. I found a nice long wavy brunette wig that I thought would go with me. I looked up a few youtube videos for makeup but that was way too intimidating. I figured some mascara and lipstick would do the trick. I told Steve it was best to wait for the weekend that way we didn't need to worry about time on a school night. By the time Friday rolled around everything was at Steve's house and I was super nervous but excited. I shaved my face,legs, and chest and I even went to get my back waxed at my place. As I walked into Steve's place I could only sense that this was a night of a fantasy coming true. I walked into his bathroom where all the boxes were there for me. Shivers went up my spine as I put on the panties, thigh high nylons, bra, and wig. As I went to open the makeup I noticed a package of long fake red nails that I hadn't ordered with a note from Steve "don't forget these". I just smiled as I knew he was just as excited as I was for this to happen. I put on the nails, mascara, and red lipstick and finally took a look at myself in the mirror. I wasn't pretty but I was feminine. For this being the first time, I was happy with the illusion. I warned Steve I was ready as I walked out the bathroom.
Steve stopped looking at the television and looked at me and said "hello beautiful". I started to blush and thought that this might have been a mistake as I was definitely getting turned on. Steve got up to meet me and he grabbed me by my hips,pulled me close, and asked "what is your name, pretty lady?". My knees got weak and I got tongue tied as I hadn't even thought of a name. After a few moments I said "My name is Gina, Steve". "Welcome Gina" Steve said as he walked to the couch and we had a sit. A feeling of "this is different" came over me. Typically Steve would just have a pillow between his legs ready for me to kneel but this time sat me down, offered me wine, and asked me about my day. As we talked I noticed how he had his arm around my waist and his other hand on my inner thigh. Somehow Steve was turned on by this and a sense of feminine pride came over me. As we relaxed and talked I put my hand on Steve's growing bulge. I was excited to get to the main event of the evening.
As I moved down to my knees, I realized I was a new person giving this blowjob. It was going to be Gina's first blowjob and she had already agreed to swallow. As I unzipped Steve I noticed my red nails again. When I pulled Steve cock out, I just kept looking at the nails around his cock. As Steve got harder I have his head a kiss and left lipstick on it. I looked up at Steve and made eye contact as I took his cock in feeling it get harder by the moment. This one was a bit different from the other ones I had given in the past. Slower and more gentle. I didn't want this one to be over quickly. I gave more attention to his balls even sucking on them on multiple occasions which is something that I didn't do before. I was feeling submissive and feminine. I let out the most feminine voice I could and said "papi you're so big and hard". We had been going at it for over 10 minutes when I knew it was time to get to the home stretch of the evening. I got into a rhythm taking him in and out the deepest I could without gagging and only using my mouth. Steve asked " you like that beautiful?" and I only stopped for a second to respond " papi I love it" as I got back into it. After a couple of more minutes I could feel him getting close. I was so used to being ready to pull away that I knew I had to fight that urge. Instead I focused on him, his hardness, warmth, and taste. I kept the normal pace but tried to get just a bit deeper each time. His moans were getting louder and longer letting me know he was almost there. Finally his cock started to twitch and his cum filled my mouth. I just swallowed as fast as I could, keeping the pace to suck all I could from his draining balls.
Over the next few months this became our regular thing. I'd dress as Gina each time and he would fill me with cum. We eventually got it to more than one round an encounter. In the time between the sessions we would watch movies, videos, watch tv, listen to music, or just talk. When we talked he would bring up fucking me but I kept telling him how uninterested I was on the matter. I did however notice, a couple of months into the situation, how he would hold me close, kiss my forehead, and compliment me. I thought he was just being sweet and I was just playing a role. However as I came up one night after we finished he planted a kiss straight on my lips.
I just froze, stocked from Steve's list on my stagnant lips. He kept going though and after my stock I found the kisses to be pleasurable. From then on we started to make out like a couple of teenagers between rounds. Each time going a bit further than before. Kissing my neck, licking my ears, playing with my nipples. He would also dry hump me grinding his hard cock on my ass. This would just get me going when he was ready for the next round.
One late January Friday evening, I got to Steve's house in a mood to blow off steam with Steve. I turned into Gina and we quickly got on the couch to make out.Steve really started to push all the right buttons that night. He must have been trying to place hickies everywhere because felt him all over me. His cock was hard and grinding deep into my ass. As Steve returned to kiss my neck I let out in a soft voice "fuck me Steve".
We both froze, did I say that out loud? Steve looked at me, got out of his shock, and pulled me off the couch and directly into his bedroom. Still in shock, he kisses me again and leads me to his bed. All I can do is think "do I really want this?", "what if it hurts?","OMG this feels so good". He had just hit my weak point again. "Fuck me" I said. My inner desires that I didn't know I had made my choice for me. As I opened my eyes and looked up to see him smiling ear to ear. "Do you have lube?" I asked. He quickly grabbed a tube he had and handed it to me.
There was a part of me that couldn't believe I was doing this, then the other part that had been waiting to get out that was very excited. I asked him to lube me up. Over the next few minutes he worked a couple of fingers into me. It hurt but he was gentle. I pulled Steve to me, grabbed his cock and gave a bit of a blow job to get him hard and started to lube him up. This was the moment I never knew would come. I got on my back, spread my legs, and Steve cock started to enter me. It hurt but I was so turned on, that I didn't want to stop. He pushed into me slowly thrusting while making headway into me. Once he was fully in he gave me some time to adjust to him. He started to kiss me again, lips, neck, ears, chest and repeat. As he started to go into me the pain started to become pleasure. I felt so good to have him inside me. I'd never felt so powerless, vulnerable, exposed but yet the pleasure won out. Eventually he started to do longer strokes and the emptiness if it all just wanted filled up as quickly as possible. I started thrusting myself. As his pace was moving I knew he was close and I knew I wanted him to cum in me. I wrapped my legs around him and helped him push into me. After a few big pumps he let out a moan, pushed into me as deep as he could and I felt his cum inside my body.