Don't forget to close the drapes

By James James

Published on Jan 13, 2006

Transgender

Controls

As I checked out of the small motel in the small Mississippi river town that I stoped at during my road trip to no where special, the young woman behind the desk asked me where I was headed.

"No where special just on a late summer road trip" I replied.

She said " I don't mean to embarass you by this comment but you should be sure that your drapes are all the way closed in the evening." She blushed as she spoke. I blushed as she spoke.

"I am sorry if I offended you. What did you see?" I replied.

"Well lets just say I loved the color of your panties." she said.

"Oh Boy. I truly am sorry you saw that and very embarrassed"

"Well don't be sorry because I enjoyed the whole show. I only bring it up because if you are that careless with the drapes at some other place you might find yourself in trouble. You know what I mean? "

"Yes and I am very grateful that you didn't report me to the police. Can I ask you what you meant by: you saw the whole show?" I replied.

"This isn't so nice of me either but I couldn't take my eyes off you and the the porn tape you were playing." she blushed again. "I watched you until you were finished."

"You must have enjoyed watching or you would have left. I think you are the only one to have ever seen me in panties. What's your name?" I said.

"Carol and yes I was fascinated watching you. I didn't know men enjoyed girls panties so much."

She handed me my receipt and said "Enjoy yourself tonight but be sure you close the drapes."

"I could stay tonight and leave the door unlocked. You could have a better look. I hate to admit it but it turns me on to know that you were watching"

"That could be fun except it is a little frightening to go into a room with a man I know nothing about"

"Why don't we go to dinner and get to know each other a little better. If you change your mind that's OK. I could always leave the drapes open a bit again" I joked.

Needless to say I checked in again and spent the day getting hard and soft over and over thinking about what tonight could be like.

Carol went home and called in sick for her evening shift.

At dinner I agreed that I would not touch her nor require her to do anything beyond watch. She told me that she thought she would really enjoy watching as she had never been married and didn't know a lot about men and their sexual being. She also said she would probably be a bit embarrassed for the same reason but admitted that like me she enjoyed masturbating. After all there were no men in her life and urges do occur.

I drove to the motel as she didn't want her car in the parking lot. I promised to bring her back to her car any time she wanted to leave.

She retrieved a small bag from her car stating that she had brought a bottle of wine to ease her nerves.

We slipped into the room and she made sure that the drapes were securely closed while I opened the bottle of wine.

I told her that I would like to watch some of the chick's with dick's cd that I was watching the night before and she nodded her consent. I propped the pillows up on the bed and she sat in the chair.

Little was said during the first few minutes of the cd. I was beginning to get hard and wasn't sure how to proceed. I needed to get my panties on. So I just lifted up my butt and took off my cloths. My dick was at attention and so was Carol. She was watching every move. I got up and went to my suitcase to get a pair of panties, black sheer boy cut and pulled them on.

She said "Cute."

I went back to the bed and began rubbing my dick through the smooth material. Raising my knees and playing with my balls.

"Does that feel good?" she asked.

"Mmmm" I said.

My hand was now going in and out of the panties and I was getting pretty excited. She was watching intently. I had to stop or I would have an early ejaculation and the fun would be over.

She asked "What's wrong?". I told her.

"Yeah" she said "I was just really getting into it. And feeling at ease with you." Then she said that she had some other things I might like to wear in the bag she brought. Maybe you could try them on while we are resting.

"Great. What do you have."

She brought out a night gown and a pair of matching white panties. She said she bought them for me. That they were way too big for her.

I got up and removed my panties. My dick was now semi erect. I pulled the night gown over my head and my dick got instantly hard again.

She said "I see you like it" and smiled.

"Feels great" I whispered. "I think I'll leave the bottoms off." I continued.

"Good" she said. Then she added "Would you ever like to get fucked like the cd we are watching?"

"I've thought about it a lot but am not sure if I would like it" I admitted.

I pulled the nightie up and began to once again stroke my cock. When I looked at her again her hand was inside her shorts.

"You can take off your cloths if you want" I suggested.

"May be just my top and shorts but leave my panties on" she replied as she stood up and removed her top and shorts.

"Wow I love small tits and the red panties may put me over the top" I said.

"Not yet" she said "Slow down"

"You look real wet" I remarked. She nodded yes as her fingers were working beneath the red panties.

I went back to my dick after putting a bunch of KY jelly on my hand. My fingers soon found my ass and I applied pressure to enter. Once it slipped in I told her the end was near for me. She stopped what she was doing and moved closer for a better view.

I stared at her cute little tits. Her nipples appeared to be as hard as a rock. I looked at her pussy covered only in the wet small piece of cloth of her red panties. I vision myself sucking someones cum from her pussy as I began my forceful orgasm. I shot gobs after gobs on pleasant cum first into the air and then finishing with in running down my hands. I removed my finger from my ass and smiled at her.

"What do you think?" I finally asked.

"Awesome" she said. "I have never seen anything like it before. I didn't know it could shoot so far in the air with such force."

"That was because you were here" I replied. "You made me have a strong orgasm. The best of my life! Thank you! I'm glad you weren't discussed."

"Oh no" she said "I loved every second of it!"

While sitting there in my nighty and her topless and in wet panties I told her that I thought she was very attractive. I liked her small perky breasts, long tan legs and a very pretty face. I got up enough nerve to ask her if I could see her pussy. Just to pull aside her panties for a look see for me. I told her if it was No that would be OK.

She said I could if I wouldn't make fun of her. First I didn't understand why she would think I would make fun of her pussy and secondly with what I had let her watch how could I make fun of anything she did?

She said " I have a very large clitoris and the only two times she had any intimate relations with a guy he gave her a bad time about the size of it."

I assured her that I would love to see her large clit and would be honored to be allowed to see it.

Slowly she pulled the crotch of the panties to the side. The first thing I noticed was how wet her crotch was. Then I got a look at it. She was right it was the largest clit I had ever encountered. I was at least an inch and half long protruding out from the rest of her pussy.

I loved it and I told her so. It was great I told her and that I would enjoy sucking on it.

"Do you really mean that?" she asked.

"Take a look at my dick it is standing up as hard as it was a few minutes ago. Your sexuality did that to me! How could anyone make fun of such a beautiful site? Put your finger back in as I am sure you haven't cum yet as I interrupted your pleasure with my own."

She looked me in the eye as she slowly slid a finger into her honey pot. I almost came just watching her.

"May I suck on it while you do that?" I asked.

"Why would you want to?" she replied.

"Please" I replied. "I'll stop whenever you say."

I lowered my mouth to her pot of gold. Her smell was beautifully feminism and sweet, her taste was wonderful and the feel of that large sensitive clit was something I have never experienced before and never wanted to stop. She thrust her pussy up and into my face. Her orgasm started shortly after I felt her clit. She pushed my face away so that she could do the things to her clit that had brought her to her orgasms in the past. I watched fascinated as it built to completion and she worked her pussy to what appeared to be a wonderful completion. She gradually slowed down and opened her eyes and smiled at me.

I told her how I felt about giving her oral sex and watching her work her beautiful pussy.

She said "I can't believe you enjoyed doing that to me."

"Well I did very much enjoy all of it! Take a look at my dick. It is as hard as it was an hour ago and you made it that way!"

"I see" she said "and it looks like your nightie is quite a mess as well."

"I would love for you to take off your panties, spread your legs a bit more so that I can see your pretty pink pussy while I jack off one more time" I replied. "A little more mess on the nightie won't hurt."

She accommodated me by removing her panties, which were also quite a mess, and spreading her pussy with her hands so it was quite wide open. I noticed that her clit had reduced it's size but was still very visiable.

I once again began to play with myself fixing my eyes on the prize. "I'm sure this won't take very long" I told her.

She said "No hurray. I am enjoying watching you as much as you said you enjoyed watching me."

Again I lubed up my hand and my ass. I pulled up the sticky nightie to give me better access and her a better view. It was really exciting to know someone was watching my most intimate actions. This time I slid two fingers into my ass and found the prostrate. Ohh that feels good. I was pumping my dick at at slow pace while I eyed her dripping pussy. The sight, the smell the sticky fingers the remaining taste of her in my mouth all added up to another smashing orgasm. I moaned loudly as I pumped my ass and squirted my stuff all over my chest. I was spent. She clapped and said it was very interesting.

I needed to shower before I returned her to her car. On the way to the car she said I could spend the rest of the evening at her house. She told me she would take tomorrow off as well even though she needed the money. She said that I might like to try on some of her intimate apparel and she had some toys that I might also enjoy. Done I was hooked on her and her great attitude towards sex.

Tomorrow is another story of sex and cross dressing. Tune in if you like.

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