A Crossdresser’s Dream Come True

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These are my experiences as a crossdresser. I am now 45, married and hadn’t been with a guy as a crossdresser for a long time until recently, which is what I am writing about.

When I was younger, I always gravitated towards being a woman and experiencing sex in that way. I did my research on being a CD, from getting my eyebrows thinned, shaving my body completely (thankfully I have little hair to begin with), keeping my “pussy” clean for sex (enema, eating right), makeup application, pre and post-sex stuff, etc etc etc.

I had sex as a fem CD (bottom only) with a few guys when I was younger and single. I was with a couple guys multiple times, but never more than a few meet-ups. I felt embarrassed to go back and not sure if they really liked it or not, etc. None of the guys I was with were anything to write home about either. Only two were younger than me and of those two, the one only wanted to take a bath with me and let me blow him, which I did. When in the bedroom later, he didn’t want to have sex with me, but he let me ride him (we were both naked) until I orgasmed on his stomach. Better than nothing I guess.

The other guy, who was the last one until recently, did have sex with me. I was 31 at the time and he was 19 and of Spanish descent. Of the few guys I was with up until that time, he was the best. I realized I liked younger guys and he was cute. After being with a few guys already, I really had started perfecting being a woman and knowing what really aroused a man. The only regret I had with him was that I had “stimulating” lube, which he didn’t like and said felt “hot”.

He didn’t have a lot of experience and only had sex with one person before me, his girlfriend, who he was still dating. He was the only guy I asked to fuck me bare and I couldn’t believe he agreed. I don’t know if it was a speech barrier thing or what (he spoke English, but not well), but he didn’t tell me when he came in me, which I asked him to do. It was still good though and I enjoyed it.

We had sex three times that night and the room had a mirror I could watch us in, which I also like. I also got fucked in all the positions I liked… riding, doggy, lotus, on my back. I only came on the last one in his lap with my legs wrapped behind him (lotus position). I could tell, despite my weight, he was really hard and about to cum himself. It absolutely felt amazing and I sat there for a few minutes afterwards as we kissed.

After leaving, I drove him home to the apartment complex he was from and never saw him again. Kind of regret it. I actually stopped dressing altogether and went back to dating women.

Flash forward to present day.

As I said, I’m 45, married and not as fit as I was back then. I’m 5’9″, 215, not unhealthy by any means, but definitely have some curves and all the great stuff that comes with age. I have a great career that has me traveling each week to cities all over the US.

About two years ago, I started to get the itch to dress again and have sex as a girl. I don’t know if it’s a mid-life thing or what, but the thought would just get me super hard. I started figuring out where I could post ads to find the right guy. I started getting myself back into being a woman… shaving my body, slowly building a small wardrobe of things (which I have to keep hidden), finding my appropriate bra size and sexy lingerie that works for my curves and body type (yeah, this wasn’t easy), going to youtube and learning makeup all over again, etc.

After a while of working on this, I packed a bunch of stuff and took it with me to “play” with in my hotel room. I dressed one night and set my phone to take some delayed pics. Now I had something to post with… and so it began.

I can’t tell you how many times I’ve posted ads looking for the right guy. Fuck it’s not easy. Being older, I am more selective. I was looking for a college guy (18-21), twink-type body, top only, nice cock, safe and takes care of himself (non-smoker, good hygiene, etc). Yes, I know… nearly impossible to find for a 45 year old curvy CD.

Of course I am willing to make exceptions, but I figure if I’m putting in all this work and willing to give some guy an amazing night of sex, he should be worth it. I had some guys I was willing to consider, but some were 50+, etc and when it came to details, they’d get weird like tell me I couldn’t call or text them because their phone broke, however they wanted to meet. Nope. Despite all the bullshit, which I am not about, I won’t forget a reply I got from a college guy in TX.

I was going to be heading to Texas and so I posted for Austin and Houston Texas with “surrounding cities” also. I got a reply from a college guy who went to Texas A&M and I was actually going to College Station bursa merkez escort TX that next week. He posted he was 18, 5’6″, 125 and had a pic of his neck down in front of a mirror, showing his abs with a pair of boxer briefs on. OMG, HOT! I thought, but also wondered “WTF does he want with me”.

He said he was open to meeting if I can host. In exchanging email, we shared more pics, he gave me his number and we were eventually able to talk. He was apparently into thicker girls and was dating one who went to school with him and was taller than me even, with big breasts and curves. He said he was closet about wanting to experience a CD or trans, but had been thinking about it for a while and wanted to try it out.

We had some great conversations and both of us were excited to meet. Finally, I got into College Station and to my hotel, texting him in the Uber. I told him to give me an hour to get ready and meet me. His dorm was only a few miles away. I brought ALL my stuff. Anyone looking at my suitcase would think it was for a woman. I was already shaven from getting ready earlier, so I showered, did my nails, makeup, applied sexy smelling body lotion, set out the box of condoms and bottle of lube next to a hand towel, got out a pair of panties and set them next to a pad and tampon (for after), etc. I was so excited. Of course, I was thinking also though, what if he doesn’t show.

He texted he was here. A few min later, a knock at my door. My heart was racing. I couldn’t believe it. I looked in the peep hole and it was him! I was as giddy as a school girl. I opened the door. In a fem voice (which I can still do well), I said “hello”. He smiled and came in. I put my arms on his shoulders and asked for a kiss. I’ll never forget his hands went down my back gently to my waist, then my butt. We kissed for a few min and then I slowly reached down and felt his cock. He was starting to get hard, so I asked him if I could take care of it. He looked at me and said “what do you think?”

I led him by the hand to the couch and got on my knees in front of him as he sat down. He had athletic shorts on, so down I pulled and out popped this amazing cock. He was huge! I remember not waiting a second. In my mouth it went. I didn’t deep throat because of my eye makeup (make my eyes water), but I sucked him for at least 5 min until I couldn’t take it anymore. I remember looking up as his head was tilted back and asked him if he wanted to fuck me. He joked and said “no” and that he already had a girlfriend, then smiled and got up with me.

I went for the lube and condoms and started to think it probably wouldn’t hurt to ask, so I asked “I know we said we were both safe, but do you trust me?” He didn’t know what I was getting at, so I held up the condoms. He looked at it for a second and asked me if I was with anyone else besides my wife, of which I said no. He then nodded and said, “yeah, if that’s what you want”. I was super hard at the thought… could have probably cum right then and there.

I turned around, put the condoms back and grabbed the lube and the towel. I started kissing him again and took his shirt off. Wow! His chest muscle and abs were perfect. I gently shoved him on the bed. As he readjusted, I pulled down my thong. I now only had a slip on (with bra under to keep my breast forms tucked in). I started fingering lube up inside of me, then got on the bed and put some on his cock, stroking it a bit. He was very hard. My heart was pounding fast. After I put enough on, I closed the lid, wiped my hands and put one leg over him to get on top of.

I remember thinking at that point how I’m going to crush him. lol He’s like half my weight and I’m around 215. I had a knee on each side of his body and as he grabbed my hips, I guided the head of his cock into my “pussy” and started to slowly sit down. OMG! Feeling the head of his cock pop in me and feeling his shaft slide all the way in me cause me to pre-cum. Here’s this cute college guy, 27 years younger than me, taking control and making love to me bareback!

Chills went through me and it felt amazing. I put my hands on his chest as I sat upright and started riding him. His chest was defined like his abs… so fucking hot! I remember thinking I had never felt sex this amazing… EVER! After going slow and getting loosened up, I started riding him harder, sliding back and forth and feeling him deep inside me. I couldn’t help but make a bit of noise too. I kept saying “fuck me, baby, fuck me!”

He got to a point where he was close and I remember bending over and kissing him. When I sat back up, I said “cum in me, shoot it deep, baby!” I think he then said “almost”, but he wasn’t as loud as me, so I couldn’t tell. bursa escort bayan He was definitely turned on and working me though. I told him to tell me when he was cumming and to look at me when he did. I remember also yelling “breed me!”.

Right after this, i could feel him squeeze my hips harder as he started saying “I’m cumming! Fuck!” The cute look on his face did it for me. As he was finishing, I started cumming all over his chest. Some of it got on his neck too. lol. He came for a good while too and got done just before me. I came a lot too, as I hadn’t masturbated in a while, knowing we would meet. I was sweating and panting. He was too. I bent over with him still in me and we kissed. Wow!

I couldn’t believe I was able to cum like this. I had never been able to hands free. I think it was partially because my “clit” was rubbing on his stomach and the fact I was so turned on… more than I ever have.

After we kissed a bit, I sat back up and remember asking him how it was. He told me I was hot and turned him on a lot. He said I was really tight too which felt good. I wanted to know how I compared to his girlfriend, so I asked. He said we were both amazing in bed. I was hoping for better, but we weren’t done yet. lol.

After wiping my cum off his chest and neck, I had to figure out how to get off of him without dripping cum everywhere. I had no idea how much cum he shot in me, but he said he could cum “a lot”. I gently lifted my leg off him and didn’t feel anything coming out right away, so I went over and grabbed by pink Victoria Secret XL cheekster panties and slipped them on halfway as I grabbed a pad.

He asked what I was doing, so I told him how I’ve had guys leak out of me in the past and didn’t want sticky panties, so I brought pads. Apparently his girlfriend did the same, so he understood and asked me which kind they were. I told him I like wearing Always ultra thin size 3 with wings. I explained and showed him I had overnights size 5 for bed and Tampax Pearl S+ tampons with me also, which are ones I’d wear when we were done, depending on whether I’m going out dressed after, going to workout or going to sleep. He laughed and said “I hope that’s not anytime soon”.

I smiled, pulled up my pad and told him he better not be leaving and that we just began. I then started sucking the left over cum off his cock, then climbed back on top of him. We kissed for a while, then I rolled over as we cuddled and talked. He spooned up behind me and wrapped his arms around me, caressing me and making me feel protected.

I turned my head and kissed him until we both stopped because we could hear the room next to us having sex. lol. We both laughed and I asked him if he thought we started that. We were definitely noisy enough. He then said we should probably show them up.

A burst of excitement shot up through me as I rolled over on my knees and started sucking his cock again. I then grabbed the lube and towel to get him ready. It was like we were in a race to start having sex since the room next to us was! lol I asked him if he would fuck me doggy style as I lubed him up. He said he loved that position. I began to pull my panties down and couldn’t get them past my knees before he pushed me over on all fours and grabbed my hips.

I didn’t get a chance to lube myself again, but as I pulled my panties down, I could feel his hot, sticky cum which soaked into my pad, so I figured there was still enough still in me to do the job. I looked between my legs at my panties and couldn’t believe how much had leaked out of me. I only had that pad on for 15 minutes!

He gently stuck the head of his cock in and started fucking me. The feeling of him going in and out was amazing. I was so wet and my “clit” was so hard. He was louder this time and I was too. Pretty sure the couple next to us realized we were in competition.

After a while, I arched my back up, turned my head and started kissing him as I was in a kind of upright doggy position, almost like I was sitting in his lap with his arms around me. After a minute, I pulled away and got on my back, kicked my panties completely off and yelled “fuck me deep!”.

He got on top, between my legs as I wrapped them around his back. He stuck it in my pussy and started kissing me. He was panting and breathing hard, as was I. He then put my legs back toward my head and was able to go really deep. I was soooo turned on as I grabbed his sexy tight butt cheeks, pulling him in me even more. He had one hand under my butt and the other on my face as we kissed. His legs were moving as he kept trying to gain the best traction to thrust into me. The headboard was hitting the wall by now. He had so much stamina!

Afraid we were making too much bursa ucuz escort noise, I told him I wanted to try a certain position, but wasn’t sure how he’d like it. He asked what is was, so I told him it was the lotus position. He had no clue what it was, so I described it. He said he actually did this with his girlfriend once, but didn’t realize that was what it was called. I was worried that I would be too heavy for him, but he said he didn’t think I was.

He began to sit up on the bed as I waited to slide onto him. He was able to pull me towards him and on his lap. I loved that I didn’t have to do much. He had me handled. I leaned to the side, slid him back inside me, then sat down in his lap and wrapped my legs behind his back as we sat Indian style with me on top. I remember thinking that with him shorter than me, I had to bend my neck down a bit to kiss him as he looked up at me. I asked him if I was too heavy and if this position was ok. He said I was fine and that he actually liked the feeling of me sitting down on his lap with him inside me.

We kissed as I rubbed my hands through his hair and gently scratched his back with my arms folded over his shoulders while as he passionately made love to me. He was strong and had a his arms firmly wrapped around me with every thrust. This was my favorite position. I felt so protected and was turned on. As he had me on his lap with my “clit” rubbing on his stomach, I could not do much more than move my hips with the motion of every thrust he made in me. He was hard and grabbing my butt. I would occasionally look down and we would kiss.

I was getting close. I could feel I was getting wet on him with pre-cum. He told me it was ok to cum without him and said he would cum soon. I couldn’t help it anymore and started cumming and shouting “I’m cumming baby! Don’t stop fucking me!” I remember squeezing my legs tight to keep him deep inside me as I exploded. I’m glad he held me tight because I turned into a jellyfish for a second after I came.

He kept fucking me and was getting faster. I could tell he was close, so I got it back together and started riding him. He said “fuck, I’m close!” and then he tensed up with his arms around me and in a deep voice yelled “Oh fuck, I’m cumming!” super loud. I could tell it wasn’t as long as the first time, but I’ll take as much of it as I can!

After he came, he was sweating and out of breath. I asked him if he needed me to get off his lap. He said “only if you kiss me first”. After we kissed, I pried myself off his lap, grabbed my panties and changed my pad. I was so sore. Not just my “pussy”, but legs, back… everywhere. Sex is a workout at my age!

We had sex a few more times that night, where he fucked me and came in me doggy once more, I rode him front and back on the couch and again on my back, with him cumming in me this way as we kissed.

We had great conversation between each round and shared laughs too. I told him if he got me pregnant, he’d have to marry me. He said he promised he would if that happened. lol He’s so cute! After being with him, I honestly would consider it if he wanted to be with me. We have such a connection and it was the best sex I ever had. It feels better than sex… as if he is making love to me. He throbs harder every time he looks at me. I know this sounds naive, but I may have fallen in love with him. I think of him all the time and we text and chat whenever we can.

Since that encounter, we’ve met two other times when I was in town over the past four months. Each time was amazing! We try new positions all the time and funny things have happened like us getting caught in the morning.

As a high tier member at the hotel brand I frequent, I get a late checkout when I want, but the housekeepers are never told by the front desk. After spending the night, we had morning sex and the housekeeper walked in thinking the room was empty. Whoops. It was very obvious too. She saw him fucking me on the couch, with me reverse riding. She stood there for a second, then tried to hide a smile as she blushed, apologizing as she closed the door.

Once he left, I apologized to her (with a robe on of course) when she came back later. I was still fully made up as a girl, but wasn’t embarrassed of pretending to be a woman. Although I may be somewhat passable, I’m sure she realized I wasn’t a real woman after seeing me naked, but she was ok with it and asked me if that was my boyfriend. I said “kind of” and smiling, she said “he was cute”.

I’ll never forget the times we are together and look forward for more to come. I am not 100% passable, but we’ve talked about going out next time. He said there is a bar called Halo that was fun and is transgender friendly.

I’ve never felt more like a woman ever when I am with him. He treats me like a lady and knows how to take charge and make love to me. He makes me feel so protected and loved. If he wanted to marry me, I would honestly consider it and move to becoming a woman full-time. The very thought of him gets my heart racing.

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