American cross dresser in Europe

Crossdressing has always been fascinating to me. Ever since my days in high school, crossdressing has been a secret obsession. It all started with the fact that I’m the youngest of 4 kids, with three older sisters. All 3 sisters where out of the house when I was in high school, but two of my sisters were still in college and left a bunch of old clothing at the house. This is where my crossdressing journey began. One day when parents where out, I snuck into both of my sisters room and stole a pair of white cotton panties and black pantyhose from one sister and black lace panties and white tights from another. The instant I felt the material of the panties against my crotch and the nylons against my legs, I was hooked. The rush I felt was addicting. Every day when I got home from school or hockey practice, I’d lock myself in my room and wear their panties and nylons. The rush was to intense, so I wanted more.

When I went to college, I did not have the opportunity to dress up as much anymore. The desire was still there but not thenopportunity. However, at this point, I knew I was attracted to men as well and girls and first started hooking with guys at 18 in college. I hooked up with men sparingly until I got my own place at 24. That’s when things hit overdrive for me. Not only can I have guys over, but I can dress up whenever I wanted.

My small 500 sq ft 1 bedroom apartment was my haven. I began to buy my own panties and nylons to wear and would wear them at home when the mood struck. I love the feeling so much that I decided to up the ante. The decision was made to buy an outfit and dress at home. I went to a mall about 30 miles from my house, out of fear of getting caught. At the mall, I went to one of the big anchors stores and bought make up, size 10.5 womens high heels, opaque tights, black lace panties, and a grey sweater dress. I then made a stop to an adult store near the mall to buy a shoulder length black wig. That 30 mile ride home seemed like it took hours but wasn’t that long. I was so excited. Once I got home, I applied red lipstick, mascara, and my new wig, followed by the panties, opaque tights, and my new grey sweater dress. I put on my heels and practiced walking. Once I got it down, I looked at myself in mirror and was so turned on. My dream was a reality. I lifted up my dress and pull town my tights and stroked my cock and came within 30 seconds.

I would eventually buy more outfits to wear at home. I wanted to dress in front of someone and luckily had a married bud who I saw who loved crossdressers. One night, he was due to come over and I decided to dress for him. When my bud arrived, I opened my apartment door and he was shocked to see me in wig and makeup, in my new grey sweater dress. We spent that rest of the night having the most intense sex I had ever had up to that point. I was further hooked to crossdressing. My bud gushed about how great looked and said “the guys would love you at the bars, you should go out like this someday. This was in fact my dream, but was just to scared to try it. However, as more and more time went by, my bud’s suggestion stayed with me. I wanted to go out dressed. That is when I had an idea.

I was 26 and single at the time and really wanted to take a trip to Europe. One night, I was dressed in lingerie in bed (my nightly attire) and laid thinking of how to get up enough courage to go out to a bar or club dressed as a women. Then it hit me, do it in Europe!! I was excited immediately. This gave me motivation to start booking my trip.I decided to spend five days in London and four days in Amsterdam. I booked my flights and booked a hotel in gay friendly areas in both cities, Old Compton street in Soho to start there and then train to Amsterdam. The excitement was intense. I’d would be Steve, a tourist during the day, and Savannah, a “woman” at night.

Preparation began a couple weeks before my trip. I’d get in the habit sitting with my legs crossed. I’d practice my walk in heels, have my eyesbrows tweezed, lost 10 pounds. and had my body waxed smooth. I was 5’7 135 lbs at the time of my trip (I usually ran about 145-150 lbs). All that awaited was my trip. I was ready.

My flight to London seemed longer than it already was. I couldn’t wait to land and be free. Upon landing at Heathrow, I hoped in a cab to my hotel on Old Compton. I had one bag and one big luggage, which had my outfits and my regular clothes. I landed in the early evening and knew I’d be dressing in public for the first time tonight. The excitement was unbearable. Once I entered my room, I took a shower and began to prepare for the night. A white colored black dress, black heels, a faux pearl neckless, and a opaque crotchless body stocking, was my chosen attire for the evening. I spent two hours getting ready and having some drinks from my mini bar to gather courage. Finally, I took the plunge and left the hotel. I was walking down the street in Soho by myself, dressed as a woman. I was so scared and ducked into the first pub I could find near my hotel. This place was nice, lowkey and friendly. I was only one dressed in there so felt a bit self conscious However, after a little while, I loosened up. The vibe was really friendly and was so lucky to walk in there. An attractive fellow in his 40s sat next to me in my small booth and bought me a drink. He was really attractive, salt and pepper hair, mustache, really fit. He kept saying how cute I looked in that dress. We chatted for a while and hit it off. He was single, divorced and was a regular at this pub. I told him I was in town from the states. The more and more we chatted, the more and more I knew we might hook up. As the night progressed, his hands made their way toward my body, and would rub my nyloned legs up and down while we chatted. At one point, his hand made it up my skirt and starts to rub my hard cock over my panties. He whispers to me “you’re so cute savannah, are you staying nearby?” I tell him the name of the hotel, which he recognizes since it’s only two blocks from the pub. He grabs my hand and whispers back “let’s go now”. We walked hand and hand out of the pub as he said goodbye to his friends there. We made the short walk back tonight my hotel.

He shuts the door as we walk into my room and we begin to make out passionately. He then lifts my dress over my head, as I lower my panties and I stand before him only my pearl neck less, my opaque crotchless body stocking and black heels. He the kneels down before me and begins to slide his lips up and down my cock. I moan “oh yes”. His mouth feels so good. He’s kneeling clothed while I stand and moan. After a little while of this, he stands back up and takes off his clothes and leads me with him to bed. He gets on top of me and we make out again, while I wrap my legs around him. His head makes it way down to my my eager hole. I raise my legs and grip my heels with each hand, as he begins to lick my smooth hole. I’m moaning “oh baby yes, oh my god”. I felt so incredibly amazing. His eyes looking at me as I stare back at him. He gets up and kisses me again. I then pull out lube from the nightstand next to my bed and hand it to him. He smiles and applies the lube to his cock and my ass and then slides his sexy 7 inch uncut cock all the way in. I’m losing my mind, in disbelief that I’m living out my fantasy within 3 hours of landing. My nyloned legs dangling over him as he pumps his cock in and out of me. I’m looking up at him moaning “fuck me baby” He starts fucking me faster and faster. My bed is rattling against wall as he fucks me faster and our moans get louder. He stares at me and smiles “are you ready?” I nod and smile, as I beg him to cum in me and he shoots a huge load deep inside. I get flush from what just happened and am panting on my hotel bed. He pulls out his cut cum covered cock and starts to finger me while I jerk my cock and I yell as I shoot my cum unto my body stocking. I look at him and say “wow, so glad we met”. We kiss intensely for a bit before he gets up to get dressed as I lay on my bed in my body stocking and pearls. He says to me “how long you going to be here?” I told him for another five days and that I just landed earlier today. He laughs and says “hot!! you couldn’t wait, could you?” I smile as he comes over to kiss me before he leaves. He says “ don’t be surprised to hear a knock on your door late night.” I smiled and told him to stop by anytime. He walked out and I was by myself thinking of what just happened. It was so much to take it in and was quite arousing. I’m already having sex, dressed as a woman, just hours after landing. I even can’t imagine what else will be in store for me on this European voyage.

To be continued…………