Adventure on CL

This is a mostly true story of the first time I revealed my secret side to another person.

My name is Colleen, secretly. I have crossdressed most of my life. It has always been my little secret. But as with most people, I have had the desire to try being with someone else, and to share my secret.

I began to occasionally check Craigslist, looking for that right person. As many of you probably know, Craigslist isn't what it used to be. I did find a couple of posts that seemed like good possibilities, but I could never bring myself to hit the send button.

As was my usual style, I would write a reply, read it over, and then end up deleting it. Except on this day. I saw a post, and wrote a reply.

Hello. I have never reached out to anybody on Craigslist before. So this is all new to me. I really don't know how to start this, so I will just tell you a bit about me. I am a closeted crossdresser, and have been for most of my life. I have always had a weakness for pantyhose. I wear them aa often as I can. I have wanted to be with someone for a long time, and I feel that I am ready to make that step, and see what happens. If you might be interested, let me know, and we can see where it leads.

Colleen.

As I sat on the couch, all dressed up, and dreaming about what it would be like to be dressed for someone else, I accidentally dropped my phone. As I picked it up, I heard the tell tale whoosh sound of an email being sent. I hoped that I wouldn't get a reply, but deep down, I knew that I really did want a reply.

It wasn't even fifteen minutes later when my phone beeped, telling my that I had an email. I looked at my email, and instantly saw that the message was from Craigslist. I opened the message, and read it. I found myself getting excited as I read it. Suddenly the thought of being with another crossdresser excited me.

"Hello Colleen. Thanks for the reply. I am interested in seeing where this goes. I know how you feel. It's never easy to come out. I love sexy legs in nylons. I would love to be the first to see yours, and hopefully more. Do you have a photo?

Erica.

I read it a few times, getting more excited every time I did. I couldn't believe he asked for a photo. I hadn't thought about that. Do I send one, and what do I send? I was already in a skirt, heels and pantyhose. I found myself standing, and quickly taking a few pictures of my legs. As I looked at them, I realized that they did look quite sexy. The thought of sending them to a stranger was turning me on.

Erica, I am a nervous, yet excited about this. It is all new to me. I have never sent pictures of me to anyone before. I hope that you find them pleasing.

Colleen.

I then took a deep breath, and pushed send. I waited for what seemed like forever. Then ding! I had a reply. Now, being spurred on by my excitement, I immediately opened it.

WOW! You have very sexy legs. I would love to see them in person. I would have so much fun with them. I want to feel them, kiss them, and do so much more with them. I really hope that we can meet. SOON!

I was now very excited about this. Then I saw that he sent me a photo. I opened it, and almost came when I looked at it. He was in a white mini skirt, white stilettos, and shiny, tan pantyhose. I could see that he was sporting quite the package, and seemed very excited. The sight of another mans cock had never turned me on, until now. I looked down and saw that I had a big wet spot on my skirt. If the photo had done that, what would happen if I went through with this?

We continued emailing for a few days. I was getting very comfortable with Erica. We talked about what turned us on, what we each wanted, and about ourselves in general. I knew that the time had come for me. I had to ask the question.

Erika, I feel very comfortable chatting with you. But talking only through email seems to be a bit slow. So maybe we should meet in person?

This was my moment of truth. All I had to do was press send. My finger hovered over the button. If I did this, what would happen. Erica had see a few photos of me dressed. But can I do this face to face. As if in slow motion, I watched my finger slowly descend towards send. My mind screamed stop! But my finger ignored the command, and WOOSH, it was sent.

Ericas reply was back in less than a minute.

GOD YES!!! I would love to meet you in person. When and where?

My mind said 'You want to this, then the hell with it. Do it soon.'

I would feel more comfortable at my house. If that's ok with you. I feel that this is something I need to do soon. Probably the sooner the better. Can you make it Friday night? Say around 7?

This time I didn't hesitate pushing send. Erika replied with a enthusiastic YES! I send my address, and wondered if I would last till then, or would I back out. I just had two days to survive, and hopefully not back out.

Friday finally got here. It was the longest day of my life. I got home later than usual. It was 6:15. I had to hurry and shower and change. At 6:50 I was ready I was in a pair of Wolford pantyhose. A red sweater, A black skirt that was nice and snug, and about four inches above my knees. I finished the look with my black 4.5 inch stiletto heels. Now all I had to do was wait.

Then the doorbell rang. As I walked to the door, my heels clicking on the floor seemed to echo through the house, very loud! Do I just open the door? Do I open and peek to see who it is? I froze with my hand on the door knob. I was scared to death, yet also very anxious to open the door. The doorbell rang again. 'OPEN THE DOOR!' my brain screamed in my head.

Time went in slow motion as I turned the handle. As I pulled the door open I realized that I hadn't even looked to make sure it was Erica. Too late now. I was standing in the open doorway, dressed as a woman, in front of a complete stranger. I looked him in the face. I saw him looking me over.

"Colleen?"

"Yes, Please come in Erica." I breathed a sigh of relief that it was Erica.

Before me stood a clean, well dressed person. I was glad to see that.

"You look very nice." Erica said while looking me over.

"Thank you. Let me show you around." I gave Erica a quick tour of my house. Erica was impressed with the size of it. The last place I showed Erica was a spare bedroom where he could change. I went back downstairs and got us a bottle of wine. Then I went into the living room to wait. I noticed that my hands were shaking a bit as I poured us each a glass of wine. Soon I heard the distinct sound of heels clicking on my hardwood floor.

"In here!" I said, letting Erica know where I was. Erica came into view, and I was amazed by her looks. A white dress, which was quite short. It fit her like a glove. Tan colored pantyhose, which shined beautifully on her long legs. And white stiletto heels. I was in awe of Erica's looks. I felt a twitching between my legs, and suddenly I felt more relaxed.

Erica slowly turned around in front of me. Everything looked fantastic! I was mesmerized by how great her butt looked. The dress seemed to squeeze her cheeks together, giving it a perfect look. When Erica turned back around, I noticed the bulge in the front. My cock, twinged again. I stood and handed Erica a glass on wine.

"Lets go chat on the back deck." I suggested. Erica followed me outside. We sat and talked about our lives. I was truly enjoying myself. We finished off the bottle of wine, and I went to get another. When I stepped back onto the deck, I froze in my tracks. Erica was looking at my yard, leaning over the railing. My eyes slowly went from her heels, up her crossed legs. The sun shinning off them, brilliantly, leading up to her wonderfully tight ass.

I sat down and admired her for a while. Erica turned and sauntered over and sat next to me. She was so graceful as she walked. We continued talking. I was struggling with my thoughts. I didn't know what to do? I was enjoying being with Erica. But could I take the next step? Was I ready for it? How do I do it?

As I was struggling with my thoughts, I felt her leg brush mine. It was a gentile touch, so I thought it might have been accidental. But when it stayed there, then started to slide up and down mine, I knew it wasn't. We continued to talk like nothing was happening. But something was happening. I could feel my excitement growing, in more than one way.

Erica seemed to sense it. I could hear the soft swish of our pantyhose rubbing together. Oh that wonderful sound! I looked down at our legs. The sun shimmering off our pantyhose. I was mesmerized. Then Erica popped the heel of her stiletto off. Her shoe swung, held on only by her toes. She let it dangle there, gently rocking it as she continued to rub her leg on mine. Now I was starting to get uncomfortable. Not with what was happening, but the reaction it was having on my groin!

Then I felt Ericas hand on my knee. She was lightly stroking it, ever so slowly moving upward. Now certain parts of my anatomy were getting very uncomfortable. My dick had been pointed down, and now my pantyhose were restraining it.

I adjusted myself in my seat, and my cock suddenly sprang free. Erica noticed the sudden movement inside my skirt.

" Better now?" Erica said chuckling.

"Oh yes! That's much better."

I looked up Ericas long legs. Her tight dress didn't hide the fact that she was also very stiff. Erica then let her shoe clatter onto the deck. She ran her foot up and down my leg. All the while moving her hand up my thigh.

"Your pantyhose are so soft and smooth. I can't stop feeling them." Her hand sliding under my skirt as she said this. I made no effort to stop her. I was loving this.

I put my hand on her thigh. Ericas pantyhose felt great under my fingers. I noticed a small damp spot on her dress. But it was growing bigger as my hand went higher. Soon I was at the hem of Ericas dress. I knew that if I put my hand under it, I would almost instantly find her cock. Yet I felt the hem slide over the back of my fingers. Sure enough, I was now touching her hard on. It twitched and seemed to grow more as I gently caressed it.

I slipped my fingers along the thick shaft, all the way up to the big head. My fingers were becoming slick with Ericas pre-cum. She was quietly moaning as I spread it all over her throbbing member. I was still shocked that I was not only doing this, but enjoying it!

Erica then gently moved my hand down to her thigh. What happened next I hadn't thought about. Erica leaned over and put her lips on mine, and started kissing me! I wad caught completely off guard! Erica stopped kissing me, and pulled back a bit.

"I'm sorry. Are you uncomfortable with kissing?"

I was frozen for a few moments, trying to comprehend what had just happened. I had enjoyed it. I found myself wanting more. Without replying to Erica, I leaned into her and kissed her with a passion that I had never felt before. I practically forced my tongue into Ericas mouth. Now it was her to be caught off guard. She recovered quickly, and our tongues were dancing in each others mouths. Our hands began to explore each others bodies at a rapid pace. We kissed for what seemed like hours.

"Lets move this inside. I think we will be more comfortable." I said.

Erica stood and we went inside. Erica sat on the sofa, and I gazed at her for a few moments. More precisely, her long legs. I noticed that she left her heels outside. She ran a foot up my leg, lifting my skirt as her toes found her target. She rubbed my hard cock with her toes for a few minutes. I was very close to cumming when she stopped. She put her hands on my waist, and guided me next to her. I instantly leaned into her and we began kissing again.

I pushed Erica onto her back as the passion grew. I felt her pressing her hard tool against mine. Our legs were intertwined as we ground against each other. Erica used her feet to remove my high heels. They clattered loudly on the floor. Erica grabbed hold of my skirt and pulled it up to my waist. I felt her hands grab my ass cheeks, and pulled me into her, hard!

I was lost in the lust and passion of the moment. I was no longer thinking, but just going with the moment. I pulled Ericas dress up. Our legs were rubbing together, as were our hard dicks. We were locked in a deep kiss, out tongues fighting inside each others mouths. The sofa was creaking under us.

Erica moaned into my mouth. Then I felt her cock twitch. Once, twice, then I felt it. Hot cum shooting in between us. I felt it smearing all over me. Then I began to cum uncontrollably. I flooded my pantyhose almost instantly. I gushed cum like never before. I felt like I came for over five minutes straight.

We slowly came down, as we caught our breath. Our cum mixing together between us, soaking our pantyhose. Eventually I climbed off Erica. We sat next to each other and continued lightly kissing for a while.

"I really enjoyed that." I said, as I finally stood up and went to get the wine.

"So did I. You were wonderful."

We drank some more wine, and talked about what ever. I felt so relaxed with Erica. I felt like we had known each other for years.

Erica placed her hand on my thigh as we talked. I felt my cock stirring to life again. Erica also noticed. She leaned over and ran her tongue along it. It came alive as she licked it all over.

I reached over and began to caress her firm nylon covered ass. It was very firm. I found her pink hole, and started rubbing my finger tip on it. Erica groaned as I pushed a bit harder. She focused on the head of my cock, her tongue was doing incredible things to me. I spurred Erica on by using more fingers on her hole, and pushing harder. I felt my finger tips enter her.

Erica pulled my legs up, and against her hardness. She began to slide herself against my legs. Ericas tongue pressed harder against me. She pumped her cock against my legs harder. This caused my finger tips to go in and out of her.

Erica grabbed my cock by the base. She stood it up and wrapped her lips around it. I moaned as her moist lips slid around on it. I felt my orgasm building. I pushed my legs harder into her hard tool. My hand pushed harder on her firm ass. I felt her cock explode, blasting all over my legs. Then mine erupted again, catching Erica off guard. She gagged and ended up spitting my load all over my lap.

Erica looked up at me and we both burst into laughter. We sat back on the sofa, and went back to talking some more.

The next thing I knew, the sun was shinning brightly, and it was morning. I slowly opened my eyes, and realized that I had a slight headache. As I rubbed the sleep from my eyes, I noticed a pair of nylon covered legs, stretched out next to me. The memories of last night slowly came back to me. I smiled as I gazed over at Erica. Her dress was still pulled up a bit. I could see her cock tip hanging out from under the hem. Her long tan nylon sheathed legs, shinning in the direct sunlight. Erica looked so sexy laying there. I felt excitement starting to stir.

I quietly got up and made a pot of coffee. As it brewed, I went and changed. I put on a clean pair of Aristoc pantyhose. Then a red silk robe. It was a bit on the short side. Well actually a lot on the short side! It went about three inches below my rear. Finally I slipped my feet into a pair of red five inch stilettos.

I went back downstairs, got myself a cup of coffee and went out on the deck. I sat down and began to drink my coffee, reliving the night before in my mind. I had so much fun. I was a truly special night.

I was so lost in my thoughts, that I didn't hear Erica walking up behind me. I felt her hands on my shoulders, as she gently began to rub them.

"Good morning. I hope you enjoyed yourself last night? I know I sure did!" I said.

"I had a wonderful time! I have never had so much fun." Erica replied as she walked around me and sat down.

Her dress was wrinkled, and I could clearly see our cum stains on her pantyhose. Erica crossed her legs, and started to rub her foot on my leg.

"Still horny? You are insatiable!!" I jokingly said. "If you would like to change, you can go up to my bedroom. You can pick anything you want."

"Thanks. I'll go change in a bit. Right now I just want to admire you."

"I think you want yo do more than that."

"Well.... yes."

To be continued...