First Experience With Cross Dressing

   I was three months shy of being 17 when I ran away; I had so many reasons for leaving my home state of Michigan, and only one reason of going to Arizona, my boyfriend. After a lot of research of what I had to do to make sure that he didn’t get into trouble in case I got caught, (he was two months shy of being 18 years old). I also did a lot of planning before calling him to tell him I wanted to be there with him. Plans like time of day, along with what day of the weeks would be best. It was actually easy to get away because both my dad and his girlfriend worked Monday threw Friday second shift so any of those days during that time frame was perfect. Friends helped by turning in last minute assignments, school books, band instrument. Another friend offered to turn in the combination locks to my school lockers, and give me a ride to the greyhound bus station.

     My boyfriend called me once a week, during the conversation I asked him, “If I could save the money to leave home can I come be with you?” “What do you mean?” He asked. I stated, “I don’t want to be here, I want to be there with you. I am tired of the things going on here and only getting to talk to you once a week.” “If you are really serious about this I can get a bus ticket for you when I get paid

     The plans are in place, I am leaving via greyhound bus at 3 PM on the first day of my spring break. To by myself some time I write a letter for my father stated that I was a confused teenager that just needed some time to get my thoughts together so I will be staying with a friend over break, (which he believed). Then My boyfriend called the night before asking, “Are you ready, is this really what you want?” I stated, “More than you will ever know, I have a ride all set up to the bus station tomorrow. Are you sure you want me to come?” He simply said yes.

     We had been together for just under a year with some strong ups and downs. During our time together I learned he liked to wear woman’s panties, and lingerie; I believe it was the way that I discovered this was the most exciting to me, but just over 17 years old by this time, I didn't really know how to tell him this. Anyway, our roommates were gone at work for the day and we both had the day off together. He asked, “Would you mind if I wore a pair of your panties for the day?” I asked, “Why would you want to wear my panties when you have your underwear?” He simply said comfort so I pushed further asking what he meant by that. Faced with this suggested we switch for the day, him wearing panties and me wearing his whitey tighties. I agreed to this but didn't last more than an hour or two before I put my own panties back on.

     I couldn't believe how itchy, overly tight, and just plain uncomfortable the whitey tighties are. He asked, “Do you want me to take your panties off too.” I said, “Oh my god no. We can share my panties from this day forward. I don’t want to punish you.” From that point this escalated to him wearing lingerie at night snuggled up to me as he held me close. The only way I really knew how to “‘voice my opinion’” was to pick out the piece of lingerie I wanted him to wear at night while he lay next to me in bed.
He got home from work each night around midnight and I normally went to bed around 11 PM so I would pick out what I wanted to wear at night then I would pick something out for him that matched what I had on, lay it out on his side of the bed with a note that simply read, “Put this on before you crawl into bed next to me.”  A lot of time I woke to him coming in but I played like I was still asleep, sneaking a peak at him as he got ready for bed, I don’t know if he knew I was awake or not. Either way I can tell you it didn't matter.

     I can’t even begin to tell you how much it turned me on watching him walk around in lingerie, or woman’s panties as he got ready for work. I got so wet and horny every time no matter what was going on. My greatest mistake was being too afraid to voice how hot and horny this made me. Between my silence and minimal actions on how horny I was by seeing him this way lead him to think I didn't really like what I was seeing and that I was just going along to humor him. 

     I have since then learned to be more vocal about what I like oh her, what doesn't look so good on her, but most of all how it turns me on.
tddybr tddybr
41-45, F
7 Responses Jan 5, 2013

Very touching.

What a sweetheart you are!! :)

Does he wear dresses and skirts. Just how much do you let him crossdress?

Mostly dresses, but he does have a couple of skits that look great on him too. I have never tried to stop him from wearing woman's clothing, in fact I encourage it. I love him for who he is, not who I want him to be.

Good for you. If more women felt that way men would be wearing dresses and skirts today anywhere they want like women do.

I truly feel that anyone should be able to wear whatever they are most comfortable in and go where ever they need, or want to go without being ridiculed. It is not the clothing that makes the person a good or bad person, it is the person themselves that determine if they are good or bad.

Thats a good way of thinking but unfortunately that's is not how it is in the world.

I know the real world is to busy being judgmental about the people around them instead of worrying about themselves. I think of more people would be open minded this would change. After all when young girls gave up poodle skirts for jeans they were viewed as rebellious, troubled girls, now woman wearing jeans is excepted.

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I agree the feel of panties are a lot better than men's underwear

Great story. Glad you posted it.

Great story.

Nice made me tingle just reading it