Initial Crossdressing Adventures

Since the first article I wrote described the last time that I dressed as a woman was generally well received, I have decided to share some more of my story. To do that I will start the journey at the beginning and travel through to some of the first times that I ventured out into public dressed as a woman.

For those that did not read my initial offering let me describe myself. I stand about 5'7" and weigh just under 140. I cycle, swim and run which allows me a plausible explanation of why I shave what little body hair I have off. Anyway, back to the beginning.

As I mentioned my mom almost caught me masturbating in bed when I was 18 with my big sister's panties which lead me to wearing them under my boxer briefs to get to the bathroom. I immediately noticed that I and my cock enjoyed the silky, tight feeling from her bikini panties.

After that incident, wearing sis's panties as I jacked off became a regular almost daily occurrence. After several months of this, I became curious as to what her other lingerie would feel like against my skin. I expanded my use of her lingerie to include silk slips, panty hose and nylons wrapped around my dick as I beat my meat, all done while wearing a pair of her panties. I found that I only liked to wear her silk, satin or nylon underwear as the cotton ones did nothing for my libido. Wearing a pair of panties had become necessary while I masturbated for me to reach orgasm. Luckily for me we shared a Jack and Jill bathroom where we kept our dirty clothes basket which allowed me easy access to her sweet nothings.

One evening as I perused through her dirty clothes basket looking for the perfect panties in preparation for stroking my cock, I was severely disappointed to not find any available to wear. There was a pair of pantyhose and a silk slip which I secreted away for my pleasure later that evening.

That night as I lay in bed wanking sliding her slip up and down my shaft, I just couldn't bring myself to fruition. I determined that I needed to feel the tightness of a pair of panties wrapped around me. Without a pair to wear, I decided to try on her pantyhose. I sat on the side of the bed, rolled the right leg up until it was similar to a sock and stuck my foot into the nylon cocoon. As I slid the stocking up my leg I couldn't believe the feelings running through me. I got just over my knee before repeating the process with my left leg. Once I had both legs into the panty hose and above my knees, I stood up and pulled them the rest of the way up my legs, over my ass and cock. OMG, I can't tell you the intense feeling of being wrapped in nylon felt like, only to be heightened when I lay down and slid into bed. Feeling the sheets glide over my legs and butt was unbelievable.

I took sis's slip and rubbed it against my encased swollen cock and in just a couple of strokes I blew my load, messing myself and my sister's pantyhose. I grabbed the washcloth that I usually shot off into and stuffed it down the front of the pantyhose cleaning myself as best as possible. I didn't want to take them off yet! Being a horny teenager and extremely excited my cock was still rock hard.

I'm not sure why I did it but I decided to pull her slip on over the pantyhose. I guess since it felt so good just rubbing it up and down my pantyhose covered cock that I wanted to see what it would feel like on. Anyway, I worked her slip up my nylon swathed legs and over my ass. Unbelievable! As I rolled around in bed feeling the silk glide over my nylon covered lower half the feeling was indescribable, on my cock and my ass. It's no wonder women enjoy dressing up with this type of sexy feeling being generated just by wearing the lingerie.

In no time at all I was depositing my second load in Audrey's (big sister) nylons. Still I remained stiff as a board. I needed to go clean up in the bathroom but didn't want the feeling to go away. Being too nervous to take the chance to walk across the room wearing Audrey's pantyhose and slip, I reached for my sweatpants and pulled them on over the top. The short trip to the toilet was exotic. The strange but wonderful feeling of my pantyhose covered legs moving around inside my sweats, my ass sliding freely back and forth and the silkiness of my feet floating across the carpet was a heady experience.

Once in the bathroom, I quickly locked both doors and removed my sweatpants. My intentions were to remove my sister's lingerie, clean it up and go back to bed. When I dropped my pants and saw myself in the mirror, well my best laid plans went astray. I couldn't believe how good my legs and ass looked in her underclothes! My cock was rock hard thinking about fucking that hot thing in the mirror.

I just had to walk back and forth to see how I looked as I moved. My walk turned into more of a sashay with my hips swinging doing my best imitation of some of the girls I'd dated. The slip was slithering back and forth across my ass and cock. The feeling was amazing. For the third time that night I came, this time without even touching myself.

Reality forced me back to earth. I stripped out of these lovely items and spent some time in the sink washing and rinsing Audrey's pantyhose and slip. Using a blow dryer, I got them basically dry and put them back in her laundry basket.

As I lay in bed unable to sleep, thoughts were running through my head.

"Was I gay?" No, I really liked women and enjoyed their bodies, had no interest in men or their bodies.

"I must never put on Audrey's clothes ever again." No way that was going to happen, I was too horny and it felt too good.

"Wonder what her other stuff feels like?" Can't go there, I'm not gay, don't want to be a woman but did it ever feel good to dress like one.

Eventually I fell asleep and had sexy and erotic dreams through the night.

As luck would have it, my family was going to the lake for the weekend and I could not afford to miss swimming practice and it was necessary for me to stay home. Unfortunately, my girlfriend also was going out of town with her parents leaving me to satisfy my own needs.

Friday night after my family had left it did not take long for the desire to put on a pair of sis's pantyhose and pull on one of her short, tight silk slips to enter my mind. My manhood was hard as blue steel just thinking about it.

Striking out in the dirty clothes hamper did not deter my thoughts. I went directly to Audrey's room, pulled all the shades down on her windows and found her panty, sock and lingerie drawers. I was in heaven. I stripped out of my clothes and immediately began trying on all her different types of panties, but only the silk, satin or nylon pairs. I found that I enjoyed the feeling of her thongs as they squeezed between my ass cheeks but my favorites were her silk string bikini ones.

The wonders in the next drawer not only included pantyhose but a myriad of nylons and garter belts. These too I tried on learning that although I really liked the way that pantyhose encased my legs and ass, a pair of lace trimmed thigh highs and a garter belt just felt more sexy.

The next drawer of delight included her slips and bras. It didn't take me long to select a short silk lace trimmed black slip to slip on. I felt incredible and paraded myself to the mirror to have a look. The only way that I could describe myself from the waist down was as a sexy, hot woman on the prowl.

I decided to go a step further and went back and tried on several of Audrey's bras. Even I knew my sister had a fine rack on her. Her proud 36C's did not go unnoticed nor did they lack for fine coverings from her drawer. I chose a black Victoria Secret bra to put on, stuffed each cup with a pair of her panties and went to look in the mirror again. Not bad but not great either.

As I waltzed around her room I found myself acting more feminine. My desires were still running unchecked so the next place I checked out was her closet. I selected several short and very tight skirts to model for myself. I found it extremely difficult to get her skirts up without my slip riding way up. Eventually I would just put the skirt on, flip it up over my waist and then pull the skirt back down.

The mini-skirts were followed by several tight fitting tops. Once completely dressed I took several more strolls around the room stopping and admiring myself in the mirror. I just had to find a pair of heels to try. My sister's foot was too small for me to wear any of hers so I headed to mom's room. I was lucky enough to find a pair of 3 or 4 inch heels that I could slip into.

Trying to walk back to Audrey's room was comical. I couldn't figure out how a girl could walk in these much less dance or anything else but when I saw the way that they made my calves and ass look under that mini, I knew why they bothered to figure it out.

I spent the rest of the weekend wearing different outfits, strutting around in high heels and constantly masturbating. I even started experimenting with make-up, mascara, eye liner, eye shadow, blush, nail polish and of course, lipstick. I found that I could make myself look plausibly sexy. Needless to say, I was hooked on wearing women's clothing but only to heighten my self-pleasuring.

Graduation meant a summer off and then away to college. Moving into college meant living in a dorm with another freshman and essentially no privacy. It also meant that my sister's clothes were no longer readily available to me.

Over the summer I had pirated away a couple pair of panties and nylons along with a garter belt, bra and slip. I kept these sexy items well hidden from my new roommate. Unfortunately, I only had the opportunity to feel these intimate items against my skin on the rare occasional weekend that my roomie returned to his hometown.

This wasn't too disturbing since I had met a local girl who was attending the university as a day student. Sherry was just slightly shorter than me, very fit as she played soccer and like me was a swimmer. She had long legs, excellent butt and a nice handful of tits.

It was only the 3rd date when we ended up in her parent's basement fucking each other's brains out. Turns out that she was as much of a horn dog as I was. Whenever the opportunity was available we would be naked and taking pleasure from each other's body. The only issues were finding a private place to partake in our love making and the fact that I was terrified of her father.

Sherry's dad stood 6'3", weighed 225 and was very protective of his little girl. The first time I picked her up for a date he looked at me and said, "I want you to know that I haven't forgotten what a young man is thinking about and that before you do something that I'll have to make you regret, understand that I cherish my little girl more than anything else." Of course he said this to me when Sherry wasn't in the room.

While being afraid of her dad, it didn't stop my desire to get into her pants. The Friday night of our third date coincided with my roommate being gone. Sherry and I went out to one of the local clubs and with our fake id's we were admitted and had a great time dancing, drinking and chatting. When I asked if she wanted to go back to my dorm room with me she didn't hesitate.

Back in my room with our tongues wresting for dominance and my hands roaming freely over her tits and ass I made the big move and slid my hand down the back of her pants. I was prepared to remove my hand depending upon her reaction. I needn't have worried as Sherry's reaction was to unbutton her jeans and slip her zipper down giving me free access to be in her pants. I wasted no time and inserted both my hands and cupped her silk covered cheeks in my hands. Once again, the smooth sexy feel of a silk covered ass overtook my senses.

It wasn't long until I had undressed Sherry down to nothing but her panties. I loved the way her pussy and ass looked and felt covered in the red silk of her underwear. My hands caressed and enjoyed every part of her body. Before long we were bumping uglies so to speak and I had totally forgotten about her big dad.

Anyway, as I said before we were hot for one another and the only thing that interrupted our getting naked was finding a place. One place that was occasionally free was her parent's house which had a nice finished walkout basement. Obviously, I was always on edge whenever we would fuck down there.

One fantastic fall day we were finished with classes and took a walk through the park. We stopped and started making out. Both of us were extremely horny and Sherry suggested going to her house as her parents were both working that day. Of course I agreed although I was uneasy.

Once in her basement we started making out on the couch. I reached down, unbuckled her shorts and pushed them and her panties down off her ass and legs onto the floor. Her t-shirt and bra came next, then my own shorts, boxer briefs and t-shirts. Insert cock and away we went. I was stroking in and out of her tight pussy while trying to work my tongue down her throat when we both heard a door slam and her father call out for her.

PANIC and I mean PANIC plus adrenaline rushed through my body. I jumped up and into my shorts, grabbed my shoes and t-shirt and was out the basement sliding door in less than 10 seconds. Sherry grabbed her shorts and top and darted to the downstairs bathroom while answering her dad.

Once outside, I buttoned and zipped my shorts, pulled my shirt over my head and slipped into my shoes. Over one fence and into the alley and I was fast walking away from her house with my heart beating a mile a minute.

I'd gone about 2 blocks when I felt a vibration in my back pocket. Reaching back I found my phone, curious as I always carried my phone in my front pocket, and pulled it out. It was pink, Sherry's phone, and I was calling her. My brain wasn't working right do to the adrenaline still coursing through my veins. I answered Sherry's phone to find Sherry calling me. She was laughing hysterically and said "Well?"

I said well what?

"She said did you figure it out yet brainiac?" "How does it feel?" "Bet you look sexy!" All while laughing her brains out.

I told her to quite messing with me, that I had almost lost my life.

Sherry said, "Calm down, daddy only stopped home to pick up his jacket as he and mom are going to dinner straight from the office tonight. He never suspected a thing." "Now think about it, does something feel different."

It was then that I finally used my big head and put 2 and 2 together. Looking down I noticed that "my" shorts were really short and my underwear felt awfully smooth and silky. Duh, I had jumped into Sherry's shorts and underwear during my panic exit. My prick was immediately rock hard. I was transformed back to Audrey's room and all her sexy clothes.

"Hey are you still there?" This brought me back to reality. Here I was in an alley wearing a pair of sexy bikini panties and short shorts holding a pink phone to my ear with my girlfriend talking to me on my phone. Sherry said "Get back here and finish what you started; besides I want to see that tight ass of yours in my shorts and panties."

I hustled back to my gal's house feeling very self conscious of what I was wearing and slipped into her basement by the same route that I had just exited. When I went to put my arms around the laughing Sherry, she pushed me back against the wall.

She said, "Hold on a minute sister, I want a good look at the merchandise." She told me to walk back and forth across the room and then to spin around for her. She commented, "I seriously think those look better on you than on me." "Doesn't matter, you're mine now, drop those shorts and get over here and make me feel good."

I quickly dropped her shorts and panties and walked over to her on the couch. Sherry said, "I think somebody liked wearing my clothes, I've never seen your cock so big or so hard." "Get down here and put it to use."

I drove my cock deep into her and pounded her with no remorse. After about 10-15 minutes I felt the familiar pressure building and quickened my pace even more. With a final deep stroke I emptied my balls deep into her hot hole.

Sherry looked up at me and said, "That was unbelievable, we need to do that more often."

"What are you talking about, we fuck all the time" was my response.

She just looked up at me with a wry grin and said, "You know exactly what I mean." We stayed cuddled together enjoying the post love making relaxation. After a bit Sherry said I've got an idea, promise you won't get mad but I want to try something.

With that she pulled me to my feet and said grab your stuff and come with me. Together we went upstairs to her room. Once inside her bedroom, Sherry said, "we aren't able to spend any nights together but daddy doesn't mind when one of my girlfriends spend the night."

She became a whirlwind of activity. Sherry started pulling open and grabbing things out of drawers, going to her closet and bathroom and finally having me sit in her dressing chair. She told me to stay with her and not to get mad or hung up on anything until she was totally done.

With that my little minx started applying make-up to my face. Once finished painting my face, she handed me a pair of red nylon string bikini panties and told me to put them on. Next she pulled a pair of jet black shear to the waist back seamed pantyhose off her bed. She told me to raise first one leg then the other and she worked the stockings up my legs until she had them above my knees. She then had me stand up, and started pulling the nylons further up my legs.

My cock was rock hard and poking out of her panties. She gave me funny look and said that it looked as though I was enjoying myself and that we would have to take care of my excitement. She bent down and swallowed my cock to the root. She bobbed up and down my rock hard schlong until I blew my load into her mouth. She took every drop, rose to her feet, locked lips with me and stuck her tongue into my mouth. I could taste my own cum on her tongue.

Sherry tucked my package between my legs and worked the pantyhose over my bum, adjusting the back seems to be straight up my legs. Next she picked up a skirt and pulled that on me as well. It was made of denim and I think spandex, so it clung to ever curve on my body.

Next came a white bra, which she hooked for me and then adjusted the straps for fit. To my surprise, well to be honest this was all to my surprise, she then slipped in a pair of breast forms. I asked her what they were and she told me that she was a late bloomer and had used them to enhance her look when she was younger.

The next item she put on me was a semi-sheer white blouse that just allowed for a shadow of the bra to show through. Sherry then rummaged through her closet and came back with a pair of 4" strappy heels. She opened the straps as far as they could adjusted, slipped them on my feet and told me to be very careful that these were fairly high and walking in any heels took a lot of practice much less ones this tall.

She then turned me around and had me look in the mirror. I couldn't believe it, looking back at me was a very attractive woman except that her hair cut was in a man's style. I spun around and quickly walked across the room to her full length mirror to be able to see the entire outfit. Once in front of the mirror I turned first one way then the other before quickly strutting back over to Sherry and gave her a hug.

Sherry was looking at me very critically. I was wondering what I had done to upset her when she said, "This isn't your first rodeo is it mister?" Oh shit, I had gotten so excited that I had forgotten about the heels and had just sashayed back and forth across her room like I had been wearing high heels all my life. Sherry said, "Well."

I stumbled and bumbled my way through a plausible cock and bull story about my sister playing dress up with her little brother and a costume party contest in high school. Sherry seemed to at least accept the story. She just said we need a couple more final touches to complete the ensemble.