tagTranssexuals & CrossdressersThe Out-Of-Town Date

The Out-Of-Town Date


It had been a long week, I was tired. Walking into my new house, all I wanted to do was relax all weekend. I flipped on the television. Turning to mix a drink, I noticed I had two messages on my answering machine. The first one was from my brother in New York. I erased it thinking I would call him later. The second one was from, Dave an acquaintance that I used to work with. I had not heard from him in a while. I was curious of what he wanted.

I dialed Dave's number. After he answered, I said,

"Hello this is Mike. You said you needed a favor?

"Yeah my cousin, Jo just moved down here. She wanted to know if I'd fix her up with someone."

I was curious why he called me it had been a while since we worked together, and several years since I had seen him. After a long silence I said,

"Maybe I can tomorrow."

Sounding disappointed, he said,

"She was kind of thinking about tonight. I know it's kind of late notice, but I tried to call you earlier."

"I had to work late or I would have been home a couple of hours ago. I'll tell you what find out if she's had dinner and maybe we can get a bite and catch a late movie."

He said he would call me in a few minutes. I took a sip of my drink and thought about what I was getting into. I had not been on a date since my divorce a couple of years ago. I had really put a lot of time into work. The idea of going out with someone sounded nice. A few minutes later he called and gave me her phone number and address. I called her and left for her apartment.

Pulling into her apartment complex parking lot, I hurried to apartment 29. I was surprised and pleased when she answered the door. She had long brown hair. She was tall, I guessed six foot. Looking up she was probably four inches taller than me. Being broad at the shoulders and hips, I thought she was beautiful. She invited me in. Walking passed her; I noticed her large round breasts. Her mini skirt accentuated her long legs.

We sat in her living room discussing restaurants and movies. After a half an hour of getting to know each other we left to get some dinner. As we walked to my car, I caught myself thinking she is kind of masculine.

At 33, I had not been on a date in three years. After my divorce, I put my whole life in my work. We drove to the restaurant talking all the way. Getting out of the car, I again started to wonder. She seemed a little too masculine. We had a nice dinner and enjoyed a nice movie. Walking from the mall after the movie, we stopped in the parking lot. We kissed.

I stayed at her apartment for a couple of hours. We kissed, hugged, and got to know each other. I wanted more, but I knew she was hesitant. I didn't pressure her; after all it was our first date. When I left I wondered if there was another reason she was hesitant. On the way home I thought about her a lot.

Between her having some masculine mannerisms and her being hesitant to get close my suspicions grew. I was curious if she could be something different then what she was. After my divorce, I had some bisexual fantasies. I even rented some bisexual tapes; one even had several she males in it. Maybe it was just my imagination, but she seemed different.

The next time we went out, she drove to my place. We went out to a casual dinner and played some mini golf. After a fun round of golf we went back to my place to watch some television. Sitting on the couch while watching television we started kissing. Leaning back, she took off her top. I caressed, sucked and licked her beautiful breasts. Slowly she unbuckled my belt. Raising my hips she pulled my jeans down. Lifting my legs she pulled my pants off.

She took my seven inch cock in her hands. Slowly she opened her mouth. Moving down, she started to give me a blow job. Her lips felt nice as she went up and down. She played with my balls as she sucked me. Slowly she slid her mouth off my cock. Sticking her tongue out she licked the sensitive underside of my cock, it felt nice. She went back to sucking my cock. After sucking me again, deeper longer, she went lower and licked and sucked my balls. Sucking me again, she sensed I was close to cuming. She started jacking me off while continuing to suck my cock. I started to worn her,

"I'm cuming!"

She kept on sucking my cock. I shot my cum down her throat. She kept at it until I was clean, swallowing every drop. I turned her over hoping to return the favor. As I reached for her slacks, she stopped me. I wanted to touch her. I wanted to lick her pussy, or whatever was there. I was excited to continue, but she stood up. After mumbling something she said,

"I have to go."

I tried to stop her, but she was heading for the door before I could get my pants on. The next couple of days I knew my suspicions were correct. I had gotten to know her and I liked what I found. I called her a couple of times, but just got her answering machine. When she finally answered we agreed to meet for lunch. I told her about my suspicions. I also told her I was okay with it. I told her about my bisexual fantasies. We had a long talk and agreed to go out again.

The next time we went out, I picked her up at noon. We drove to Daytona Beach. It was a warm day for late November. We enjoyed walking on the beach and wading in the water. Towards early evening we started back for Orlando. After a stop for some take out at a Chinese restaurant, we went back to her apartment. After cleaning up the leftovers, she took my hand and led me to the couch. We relaxed with an Orlando Magic basketball game on television.

She leaned towards me. We kissed. It was a long passionate kiss. Reaching under her shirt, I started to feel her bare breast. I moved from one to the other. After we kissed again, she got up. Motioning for me to follow, we went into the bedroom. Stopping at the foot of the bed we kissed again.

Breaking the kiss, she said,

"Are you sure you're ready for this?"

Pulling her t-shirt over her head, I answered,

"Yeah are you sure you're ready?"

Without saying a word she laid on the bed. I took off my blue jean shorts and laid next to her. Moving close for another kiss, I put my arms around her naked shoulders. I moved down to suck on her round breasts. I rubbed and played with the nipples. After sucking and licking both her beautiful breasts, she reached for my underwear waist band. Sliding my underwear off, she freed my hard cock.

Reaching her hand to my balls, she moved her head to the tip of my cock. Opening her mouth, she started sucking my cock. Sucking harder and deeper, I was enjoying her every move. As much as I was enjoying it, I stopped her. I didn't want to be the only on naked. When I moved to undo her blue jeans, she said with hesitation,

"Are you sure you want to go there?"

Undoing the snap, I answered,


She raised her hips to help me. As we slid her pants down, I watched her thin lacy underwear looking for a cock. She rolled over with her butt near my chin, I pulled her panties down. All in one motion she turned and moved to the other side of the bed. Before I knew what was going on her thick eight inch cock was at my nose and we were in a position to sixty nine. Her skin was so smooth and soft it was odd to see a cock between her legs.

I opened my mouth and slowly slid the large mushroomed head between my lips. It was the first cock I'd ever sucked. I loved the fragrance. The texture of her cock on my lips and tongue was exciting. I took her deep in my mouth sucking deep and hard just like I'd fantasized. I stopped long enough to enjoy the feeling of her mouth on my cock.

After enjoying her mouth and lips, I started to suck her cock some more. While sliding her cock in and out of my mouth faster and faster, I started playing with her balls. Not being experienced, I didn't realize she was close to cumming. She shot a load of sperm in my mouth then another shot. There was so much it dribbled down my chin on my beard. I heard her moan. Between her moaning and her sucking my cock, I started cumming. She sucked me dry.

She turned around to join me. We kissed a deep passionate kiss. Breaking the kiss, we both laid on our backs and relaxed. Looking down her body I was turned on by her hair less cock. The next twenty minutes or so we walked around her apartment naked. After pouring a couple of glasses of wine, I turned to put the wine in the refrigerator. She leaned in to hug me as I stood up. As her arms came around my chest I felt her cock touching my butt cheeks. My mind started to swirl. I'd never had anything in my ass before and I wasn't sure I was ready to start then. At the same time, it was exciting. We stood there for a minute enjoying the touch.

Breaking the hug we went into her bedroom. Motioning for me to get on my back, she said,

"Trust me, but if it hurts too much stop me."

I shook my head and watched her move towards my mid section. She started licking my balls and playing with my cock. Slowly she moved a long finger to my ass. Slowly sliding it in my tight hole, she kept licking my balls sometimes moving to my ass. Between her moving her finger in and out and her adding saliva, I was getting more and more turned on.

After loosening me up with her finger she moved me on my back. Positioning her cock at my tight opening, she slowly entered my virgin ass.

"Stop me if it hurts or you don't like it."

I just groaned and pushed towards her. She pushed harder. After the first bit of pain, I was getting used to being filled up. I was even enjoying it. She started moving faster deeper, harder. I was meeting her every thrusts. Oh it was a different feeling; my thighs were starting to tingle. We were both moaning. A couple of more hard thrust and she pulled out, shooting a stream of cum on my stomach. Lying down next to my sweaty thigh, we were both breathing hard.

She reached for my cock. Playing with it then sucking it. She was sucking faster and deeper, while playing with my balls. In no time I was cumming. Lying there in our sex juices and sweat, we both enjoyed the moment. After a few minutes to catch our breath, we finished our wine and took a shower together.

Getting out of the shower, I asked

"Does Dave know that you have a cock?"

"Yes, we grew up together. It was a little awkward when I told him I wanted to move down here and live as a girl."

It was like a light bulb went on in my head, I said with an expression of surprise,

"That's why he called me. He could not set you up with someone who is still a friend or a co worker."

Jo started to grin. Breaking the grin she said,

"Yeah I'd been down here two months before he called you."

We finished drying off from our shower. After putting our wine glasses away, we went to bed.

Report Story

byrosewall© 3 comments/ 50820 views/ 6 favorites

Share the love

Similar stories

Report a Bug

1 Pages:1

Please Rate This Submission:

Please Rate This Submission:

  • 1
  • 2
  • 3
  • 4
  • 5
Please wait
Favorite Author Favorite Story

heartgod67, mister_C_Dee and 4 other people favorited this story! 

by Anonymous

If the above comment contains any ads, links, or breaks Literotica rules, please report it.
by cdCindy108/29/17

please continue

This was a great first chapter. Please continue. I can't wait to read what happens next.

If the above comment contains any ads, links, or breaks Literotica rules, please report it.

Show more comments or
Read All 3 User Comments  or
Click here to leave your own comment on this submission!

Add a

Post a public comment on this submission (click here to send private anonymous feedback to the author instead).

Post comment as (click to select):

You may also listen to a recording of the characters.

Preview comment

Forgot your password?

Please wait

Change picture

Your current user avatar, all sizes:

Default size User Picture  Medium size User Picture  Small size User Picture  Tiny size User Picture

You have a new user avatar waiting for moderation.

Select new user avatar: