Ah, memories from high school

[Kristen Smithly]

In the days of yore, well, many decades ago at least, I dated a very pretty young lady who was a year behind me in High School. I’ll call her Karen, because that is her name. Karen and I were sexually active, though she never saw or knew of my dressing, she insisted I wear pantyhose during times of intimacy. She asked the first time when she requested it if the idea bothered me (of course not!), I said no, if it was what she wanted. It always seemed when we bought hose it was two pairs, one for her and one for me. She did the garters and thigh highs on me but didn’t like it. She didn’t care for panties/bras on me either. Pantyhose was her thing. I like to think I was her first (she was a virgin when we first met) in a line of lovers in her life that she asked for this “fetish” of hers. Have any of you ever had something similar happen in your young(er) life? I can’t stand pantyhose today, more of a garter/thigh highs type of gal! I think it only continued to encourage my crossdressing even more. It was during that time I bought my pair of my own panties, (and a bra, which didn’t fit). Most of my memories from those years weren’t all that great, but on occasion I think of her and I, with me in pantyhose…

Total of 25 users thanked author for this post. Here are last 20 listed.

Gabby Ashmore, Katherine Leigh, Susan Talbot, Paula Here, Leah, April Sinclair, ChloeC, Lynda Jones, Joeleen Noel, Madeline Bradford, Peggy Sue Williams, Patty Phose, Jill Edina, Samantha Elizabeth Andrews, Suzanne Martin, Michelle Brown, Ashley Konners, Stephenie Derick, Jerri Newman

Topic

[Caty Ryan]

I attended an all male trade oriented school, (we use to call them “tech’s as in “techinical schools”)

So the only remotely CD memory I have from school days was a that they must have a had a new drama teacher the year after I left, cos I think they ran a play where some boys had to play female parts.

Damn… Missed out by a year.

Tho back in those days at expensive private all boys schools, it was common for them to run high class productions with all male casts

I still clearly remember one school doing Wilde’s “The Importance of Being Earnest” and being green with jealousy at these 14-15 year old boys done up as Miss Penelope or Lady Bracknell.

Think its one of the reasons I’ve loved period gowns all my life.

Also makes me muse that in the latter day  “attics” or “back rooms” of some high end judges/lawyers/doctors captains of industry, lies a dusty phot0 album of them in all their glory.

Perhaps one or two went further in their lives and became one of us??

These days Australian “one gender” schools partner with another opposite one to run their productions.

Happy dressing

Caty.

 

 

 

[Patty Phose]

My girlfriend in high school thought I had nice legs and thought I should wear pantyhose. I never told her I had been wearing pantyhose since I was 4 and wore them nearly everyday.

One day she told me she had a present for me. When I unwrapped and opened the box, there was 4 pairs of No Nonsense Light Support pantyhose in sheer to waist. That and Legg’s Sheer Energy was two of my Two favorite brands I wore all the time. She asked me to put on a pair, which I quickly and expertly did. I was pretty excited and didn’t think I probably should have made it look like I didn’t know how to put pantyhose on.

She kind of liked it but thought the hair crushed under my pantyhose looked strange. After a few hours of great pantyhose play, we took a bath and she helped me shave my legs. After getting out of the bath and drying off my legs looked strange with no hair on them. When I put on a new pair of pantyhose though, I was amazed my legs felt and looked so sexy. I wish I had shaved them long ago.

She told me to put on my shorts and get dressed so we could go out. I was nervous wearing pantyhose in public but she coerced and encouraged me. We went shopping where she took several more pairs of No Nonsense Light Support pantyhose and gave them to me to carry around, saying I was going to need them. Here I was wearing pantyhose and walking around a store carrying pantyhose around we were going to buy for me.

After that we went to a diner for some food. She kept touching my legs and rubbing hers against mine. The pantyhose on pantyhose sensation was wonderful. As nervous as I was about drawing attention to us, I was still was enjoying it so much.

After dinner we went to a movie. We rubbed and entangled our legs together, while gently stroking and caressing each others legs. It was wonderful.

After that, I wore pantyhose with her whenever I could. We often went out. I bought some short girls shorts and a pair of platform wedge heels that were just like a pair of hers. I wore them often when we were together. I even went out in that a few times. I was very nervous about being seen wearing pantyhose, short girls shorts and wedge heels by someone I knew, getting taunted or assaulted. Still I loved it so much and always looked forward to wearing pantyhose with her, the pantyhose play and the thrill and excitement of going out.

I thought if I had a wig and made up breastforms to put in my bra, I would look more like a girl and could go out not looking like a guy wearing pantyhose. I had wanted to do that for as long as I could remember. I wore pantyhose in public. It was scary but very exciting. Now it was time to do it as a girl.

I made some breastforms from old pantyhose and put them in my bra. Now all I needed was the wig. I saw a wig I wanted in a wig store but didn’t have the nerve to go in and buy it. I bought lots of girl clothes in guy mode and was always excited about my new things and looked forward to wearing them. But buying the wig made me nervous. After a couple of weeks I finally got the nerve to go in with a concocted story about being in a play and needing long hair. I ended up buying two wigs in the same style but different colors.

I wanted to show my girlfriend my breasts and pretty hair but never got the nerve. I began going out en femme. Even though I was incredibly nervous most of the time, my fears of being seen by someone I knew while wearing pantyhose or being taunted or assaulted for being a guy wearing pantyhose was not a concern anymore. I looked much more like a girl and a lot less like myself.

6 users thanked author for this post.

Leah, ChloeC, Kristen Smithly, Lynda Jones, Marlene Roberts

[Kristen Smithly]

My girlfriend didn’t mind if I wore them at other times, like when we were out shopping, etc. I had to take a long boring road trip from Boise, Idaho to Sheridan, Wyoming once, I stopped in a small town at a gas station in western WY and changed out of my jeans into some cutoffs (shorts) in the restroom. I was wearing some pantyhose with a slight shimmer. I didn’t even think about and across the street were some guys sitting on some chairs outside a store. I caught them looking at me and I just knew they could tell I was wearing pantyhose under my shorts. My thought was, some cowboys are going to follow me and beat the dickens out of me, so I might as well get as far down the road as I can. Nothing happened and I made it to my destination safely even with a few gas stops along the way. One lady at a gas stop said she liked the shade of my hose. She was sincere and not condescending. I thanked her, and gave her a compliment on her blouse. I quit wearing pantyhose not long after that, so no more experiences.

4 users thanked author for this post.

Katherine Leigh, Leah, Lynda Jones

[Peggy Sue Williams]

Yes!  I had experiences like that -before- I was married!

There will always be some women who are absolutely fascinated by men who are willing to model intimate female apparel for them.  Even more so by men who are willing to dress completely for them.

If you ever spend some time in Atlanta, drop me a PM, I can send you the name of a club where cis women hang out for the purpose of meeting heterosexual CDs.

3 users thanked author for this post.

Katherine Leigh, Leah, Kristen Smithly

[Kristen Smithly]

I have never been to Atlanta, may have to take a trip, and combine it with a trip Savannah (somewhere else I’d like to go).

1 user thanked author for this post.

Peggy Sue Williams

[Wanda Ovahear]

I don’t have a story like that. I didn’t date much in high school. I was one of the drama kids and a pot smoker. We didn’t date we had rehearsal. A little backstage making out happened of course.

I remember fantasizing about wearing girls P. E. kit of the period.

3 users thanked author for this post.

Kristen Smithly, Rachel Smith

[ChloeC]

I was terribly shy during my high school years, partly because I just was, and partly because I knew I was tg and I was sure that if I got too close to anyone, it would be written all over my face. So I had friends, mostly males, but nobody really close. I would have loved to have had girls as friends, to talk to, share experiences, and in a few small ways it sort of happened, but at that age and era, girls were pretty much sizing up guys for future comparisons and I surely did not think I’d compare hardly at all.

That all changed towards the end of HS and into community college (which was really just a little more libertine version of high school as we did have ‘partays!’). I started dating and for several months at a time. First girl I seriously dated, after she dumped me, she got pregnant by her next date and married him. I have no idea what ever happened to her. Another girl I dated for more than a few times, I was invited to her house and she basically ordered her parents to bed and we, um, well, that old baseball bases story took effect and all of a sudden we were way past first which prior I had hardly ever been close to.

Next girl I dated I’m pretty sure she was looking for a husband (she was a farm girl from the country and I was a city guy)…and I certainly wasn’t looking for any kind of lifetime commitment at that moment. She lived a state away, and I went to visit her for the weekend once, having to take a commuter train to the city and transfer to an express. Two young women who were good friends (one was dating my best friend at the time) came with me to the 2nd station and both kissed me on the cheek good-bye as I was going to see this other girl. That was the highlite of my involvement with girls at that age, having young women as good friends. I enlisted in the military several months later.

Hugs ChloëC

• This reply was modified 2 months ago by ChloeC.

4 users thanked author for this post.

Leah, Kristen Smithly, Suzanne Martin, Michelle Brown

[Emily Alt]

In college I dated a girl named Donna.  She graduated a couple of years before me and worked at the local TV station.  Donna was smart, sexy, provocative, and very pretty.  She also had a kinky streak.  In the bedroom she often wanted me to wear her lingerie.  Feigning indifference I always did.  Little did she know how much I loved it….or maybe she sensed it all along.  Like I said, Donna was smart.  Some of Donna’s other kinks were too much for 20-something me.  I came to realize she was a predator and I was just another one of her boy-toy conquests.  We fizzled after a few months.  I haven’t thought about her in years.  Thanks for jogging my memory Kristen!

/EA

10 users thanked author for this post.

Leah, Kristen Smithly, Lynda Jones, Marlene Roberts, Madeline Bradford, Suzanne Martin, Michelle Brown, Stephenie Derick, Jerri Newman

[Danielle Anaya]

My high school experiences were limited because of the difficulty dressing without getting caught and having to sneak out of the house. I never brought up Dani to the few girls I was with in high school and that was fine because sex with a girl was pretty amazing to me at a time when I didn’t know what bad sex was.
I only had one gay playmate at my school who I introduced to Dani. It was a surprise introduction where I literally blew his mind. Our games almost always involved me dressing like a hooker, which I guess was the fetish for him. He liked me to meet him dressed as Dani in skimpy sexy clothing. One game we liked to play was I would kind of hide in a predetermined location and he would pull up in his car. As I saw him approaching I would step out and act as if I was a street walker. He played the game of soliciting me and we would find a quiet place where I would do some hooker things with him. We ended that game when a stranger pulled up and he and my friend had a little confrontation about who was going to get the girl. That got interesting. Stupid teenage me never thought what I would do if the cops or some real creeper came by. I was only with one girl later in life that liked me to dress as a woman. She was a domanitrix type who liked me to dress in lingerie and we did some pretty crazy things. I wasn’t really into that. I do love dressing in lingerie for men now, especially with garters and silk stockings and stilletos. That’s kind of my fetish, besides playing the role of a submissive woman for my partner.

7 users thanked author for this post.

Kristen Smithly, Madeline Bradford, Suzanne Martin, Michelle Brown, Jerri Newman

[Author]

Replies