I was 5 years old and my teenage aunt was babysitting me for my mother. I got into a mud puddle and made a mess of all my clothes. My aunt, fearing my mother’s wrath upon her return, so auntie took my clothes to launder them. Having nothing else for me to wear she adorned me in a pair of her white nylon panties. To this day I remember the cool, smooth, soft fabric as it touched my most sensitive areas. I had to have more!
I got home later and found a pair of my mother’s pantyhose in the laundry bin. I had to try them on. It was like heaven! I had to have more! This went on as I aged. Taking the time to secret away something soft and silky, wear it for awhile and then put it back. One day, when I was 10, I was wearing Mother’s pantyhose under my jeans. No socks.
While playing outside, my sister noticed my “tan” ankle right away! She immediately ran into the house to “tell”! My parents brought me in the living room, yelled at me, made my drop my pants and stand there in front of the entire family in just pantyhose. My mother laughed and my father yelled! I was horrified. I didn’t dress in anything like that for several years.
Then one day at the age of 13 I decided it was time to try pantyhose again. I was experiencing the “rush” of puberty and couldn’t stop thinking about how it would feel to wear pantyhose again. I snuck some of mom’s hose to my room, put them on and even did my exercises in them.
Later I found a bra that was in a pile of “yard sale” clothes we were going to sell. I took it! It fit very nicely. I also found a one piece bathing suit that used to be mom’s in that same pile of “yard sale” clothes. I now had an “exercise” outfit. I couldn’t stop wearing that outfit. Black bathing suit, white bra, tan pantyhose. I thought I was “gorgeous”.
While laying on my side and doing leg kicks, I noticed there was a strong swelling in my “private area”. The more I kicked my leg in the air, the more I felt that “rush”. Then all of a sudden, I exploded in a way that I had never ever experienced before. It was MAGIC!! It was also, messy. I was scared and hid my clothes thinking something was wrong. BUT I couldn’t forget the experience.
So I washed the clothing, put them back on and exercised again! As you could imagine, exercise became a high point of my existence! Then I tried “self massage” while wearing panties and hose and bra and a nightgown. All purloined items from my mother and sisters. That nylon nightgown over the panties and hose was another episode of pure magic.
Fast forward to a few years later and my first real love. A very attractive young lady who had a hankering for her boyfriend to let her “dress him up”. I acted like I didn’t want to, but inside I was about to scream! I made love to her while dressed like her. I can not even begin to explain how high I was from that! It took days to come back down!!
The next time, she put make-up on me. I found lipstick to be especially sensuous!! Sharing lipstick was even more luxurious! One day we were playing dress up at my apartment when some friends unexpectedly dropped by. They knocked. We wouldn’t answer. I heard them say “His car’s parked outside, why isn’t he here?” My heart was racing.
There was no way I could be caught by them and still be able to face them later. Finally they left. But one of the girls said she could smell perfume! A couple years later that girl and I broke up. I found out later that she revealed to one of my best friends that she and I played “dress up” and did it a lot. He wouldn’t let me live it down! He bought me pantyhose and lingerie as birthday and Christmas gag-gifts. I kept them and enjoyed them, unbeknownst to him! At least that’s what I thought….
I was asked to be in a womanless beauty pageant, along with some other guys in my office. I agreed to. Oh, I acted reluctant about it, but I was thrilled on the inside. So I used the pantyhose from my friend and a dress that another friend gave me as a gag-gift when all my friends were alerted to my ex-girlfriends stories. (she turned out to be a vindictive little thing, and SHE left ME!)
My friend, who came to the pageant, asked me if I was wearing the stuff they had given me. I said “Sure, did you think I’d go pay good money for this stuff?” Trying to act like a “guy” about it. I had a female friend from the office loan me a wig and do my makeup. I was very proud of how I looked. Apparently so was my friend. After the pageant he said he wanted to talk to me. I told him I’d get changed first and he said “it really can’t wait”.
We went to his car, a 1972 Monte Carlo. Significant detail because that car didn’t have bucket seats up front. Long story short, my friend put “the moves” on me. Told me how he found me attractive, and always wanted to have girl “like me”. I was overwhelmed. I told him that I didn’t really think of him like that and that I was into girls.
He put his hand on my knee and while making his case, he slid that hand up my thigh. It was sooo warm. My heart was about to burst! I was sooo scared, confused and weirded out all at the same time. I could feel my eyes welling up and I didn’t realize how close his face was to mine until it was too close! He softly kissed my lips and then pushed in for a deeper kiss. All the while his hand was caressing my thigh, then he moved to my groin. He said “oh, somebody is a little wet!”.
I couldn’t deny it, I was very hard and very wet. I’d never had a man touch me there and I have to admit it was a thrill and a half! Just then, from outside the car, some girl yelled for my friend. Called him by name. She came to passenger side of the car. The way I was turned I had my back to her. She asked if we were coming to town and my friend said he didn’t know, but maybe!
She said she’s see us later and then went to her car and left. My friend looked at me and said “Well, that got hot and heavy pretty quickly, didn’t it?”. I answered that it did and that I had better go. I opened the door and slipped out onto the parking lot. He told me to “think about it”. Adding that we could “have a real good time together!”. I told him I would and I even thanked him for making me feel special! He smiled and said “anytime!”
I left and we never talked about that night again. I’ve been tempted to bring it up a time or two, but never did. I wish now that I had let him take me down that path…I really do.
Submitted by
just love crossdressers
Hi Susan
I can just imagine how you felt, when your friend made a move on you.
Apparently you are a hot looking girl, when you are dressed like one
Sometimes when we get dressed we don’t realize just how hot and sexy that we look and how we can affect men who see us
I had a similar experience with a man, but he wasn’t a friend like you had
Long story short ,I was at a club, to listen to a band that was playing there and I wanted to hear them
I was sitting alone, minding my own business, enjoying myself, when a man who was there, wouldn’t leave me alone.
He must have asked me to dance with him at least five times and I told him that I wasn’t interested in dancing with him
He kept coming back to the table where I was sitting and kept asking me to dance with him.
Finally I told him, just one dance and I got up and went to the dance floor with him and began dancing.
He was a great dancer and I was impressed. One dance became two and three and before I knew it, we had danced for almost a hour
At the end of the evening, he walked with me out to where my car was parked.
When I turned around facing him to tell him goodnight, he kissed me, taking my breath away
As good as a dancer that he was, he was a better kisser
My toes were curled in my shoes, from the feeling of being kissed by him and I kissed him back, not wanting the kiss to end
Susan honestly, I had never been kissed by a man before and I was really enjoying it
All we did was kiss, but I’ve often wondered what might have happened, if I had let him get in my car with me?
Instead I got in my car and drove home alone, thinking about how much that I liked kissing him and fantasizing about what might have happened
I guess that I’ll never know, but I still think about him from time to time and wonder what might have happened?
Janine,
I know how you felt and I know how Susan felt. It’s amazing how we feel during these times when we are on that balance point of tipping into womanhood. We pretend we don’t like it, we pretend we don’t want it but deep down it’s always been there and we find ourselves practically screaming for it!
My first time with a man while crossdressed was amazing and unexpected. I had no plans for such a thing to happen but when it did it swept me off my feet. My ex-wife was away on a two week business trip and I had big dressing up plans but only in private. I was also planning to have a few glasses of wine and go online into a crossdressing chatroom and have fun there. The chatroom wasn’t all that busy so I started looking around and saw a T4M room so I went in there and it was better. I knew I’d have to deal with men but since it was fantasy I figured what harm would that be? I got into a few conversations but one guy got really forward with me and told me I would really enjoy going down on him and having him inside me. Now to be honest I never wanted to make a woman give me oral sex because I couldn’t imagine anything more disrespectful than making a woman put my thing in her mouth! My ex-wife had given me a blowjob twice in our marriage and I couldn’t stand it, I pulled out because it felt horrible and asked her to never do it to me again. I ended up chatting a lot more with this man and started getting really turned on and though I was pleasuring myself I wanted more.
I ended up where I couldn’t take anymore of chat so I decided to go out and ended up going to a gay club close by. I was so nervous, I put my ID, my house and car keys, spare panties and pantyhose, some makeup, k-y and some tissues in my purse and decided to get going. I got there about a half hour later and steeled myself to go inside. I paid a cover charge, the man at the door smiled and let me in, I was a wallflower for a bit and a man come over to me pretty quickly. Apparently the man at the door told him there was someone here he might be ‘interested in’. We sat down at the bar and chatted for a few minutes and got a beer each, he bought. We moved to a corner so we could hear each other easily. I told him I was a crossdresser, of course he knew, he told me I looked really good, I told him I was married and straight and he said something like “ok, that’s nice” but I think he could tell that I was ‘curious’ at the very least and I definitely was sending vibes that I was aroused. He was very gentlemanly with me and I started getting more settled and comfy with him, also I’d had a second beer with a third in my hand and was getting more relaxed.
He asked if I’d ever gone out dressed, I said I had, he asked if I’d ever been with a man and I told him in my early teens I had experienced being with a man. He asked if I really was straight and I hesitated but admitted I was either bi or more likely gay. He asked me if I’d like to dance so I downed the rest of my beer and went to the dance floor with him. I’m not much of a dancer but I got into it, mostly just him guiding and me following. It all started on a slow dance and he pulled me close to him, he grabbed my ass cheeks and pulled me tight and I felt ‘something’ and it took me about 10-15 seconds to realize he had an erection. I was sooo shocked and actually felt pride that I caused this, I also felt desire like I’d never felt before!
He was smiling away and all of a sudden he leaned over to kiss me, I didn’t so much as let him as he surprised me. I was in shock, so much was going on, I kissed him back and then he put his tongue in my mouth. I was in ecstasy, he kissed my earlobe, took it between his lips and tongued my ear, then he kissed my neck, ran his hand up the back of my thigh and I almost lost control. I wanted him really badly right then, right there!
We went back to our quiet corner, he asked me if I wanted more, I told him I absolutely did but I was scared because I was married but I wanted him so much I was conflicted and ashamed but had never felt before what I was feeling now.
I asked if I could feel his erection and he loosened his pants just enough for my hand to go in and when I felt it I told him I needed him to make love to me. We went to his car and he brought me to his house. I couldn’t keep my hands off of him the whole way to his house, I was so aroused the whole time. We got into his house and I practically threw myself on him, I wanted him so much!
We went into the living room and sat together, we kissed, I felt his hardness and I undid his pants and saw that erect penis and got ready to go down and I hesitated. I told him I suddenly got nervous because I was a married man and I was about to cross a line I couldn’t cross back over. He convinced me that I’d crossed that longer a long time ago, when I decided he was right I went down on him in a flash. I never knew this feeling before and I wondered why on earth I ever thought this was a disgusting thing to ask a woman to do because I thought his cock was the most beautiful thing I’d ever seen. I kissed the tip, ran my tongue all over it and up and down the shaft as well. I took it in my mouth and though it took a bit I was eventually able to take it in my mouth without any trouble at all.
Through the night we went from oral to anal. I couldn’t believe the ecstasy and thrills I felt. We met quite a few more times during the remaining week and a half I was free. I didn’t always get to dress for him but the physical and sexual thrill was just as amazing every time.
I ended up staying married for another 15 years but my ex-wife caught me because I left my email open on the computer. I came out to her on my gender dysphoria and my crossdressing and she filed for divorce.
This is like that the book by Nicola Atherton, Going Out I think it’s called, that everyone’s talking about – lovely story!xxx
Believe me, if you’d gone a little further it would have changed your life. I remember my first time with a man when I was dressed. I hesitated for a bit because I was married but shortly after I hesitated I gave in to desire and it was amazing. I never ever had sex like that. My marriage lasted a few more years but I finally came out and it was the best thing I ever did.