My Tall She-Male Pt. 01

Story Info
Peter lets a tall shemale take him.
2.3k words
4.48
44.4k
59
Share this Story

Font Size

Default Font Size

Font Spacing

Default Font Spacing

Font Face

Default Font Face

Reading Theme

Default Theme (White)
You need to Log In or Sign Up to have your customization saved in your Literotica profile.
PUBLIC BETA

Note: You can change font size, font face, and turn on dark mode by clicking the "A" icon tab in the Story Info Box.

You can temporarily switch back to a Classic Literotica® experience during our ongoing public Beta testing. Please consider leaving feedback on issues you experience or suggest improvements.

Click here
JJ122964
JJ122964
145 Followers

Author's Note:

I was working on this for awhile now. I hope you like it. So far I only have two parts in mind.

*****

I woke up in Lisa's arms early in the morning. I had my back to her and her arms were wrapped around me in a bear hug. Her warmth permeated my body, it radiated from her muscled, well-toned body that I felt on my back. I smiled and snuggled back into her arms. Her cock was nestled in between my ass cheeks. She tightened her grip and nibbled a bit on my ear.

We met at the gym where we worked out. She would come in at different times and was looking for a time when there were as few people as possible. She is 6' 5", nicely tanned skin, blue eyes, and red hair which hung down to her shoulders. Her body was well-toned and looked very athletic. Her hips were a little wide but that did not stop the many men watching her who she talked with from time to time and she was very friendly.

I watched her work out when she was there, her routine showed a lot of strength training and body shaping. She had honed her body to be not so much a bodybuilder but a shapelier form. I was just trying to get back into shape after years of slacking off. Then one day I built up my nerve and walked up to her.

"Hi, my name is Peter. I've seen you work out a few times here and I wanted to say you have a great routine. I was wondering if you'd share with me how you came to it?" I asked.

"Hi, Peter. I have noticed you watching." She said smiling.

She stood and wiped her forehead with the gym towel.

"Are you sure that you want to know that or do you have something else in mind? Or somewhere else." She smiled looking at me and her hand to my crotch.

I just stood there looking up at her, my mouth opened slightly.

"How about we start off slow and get something to eat?" She suggested.

"OK, I know a nice Chinese restaurant next door." I said.

"Good, but first a shower."

We went to our locker rooms and showered. We met at the restaurant. We made small talk while eating.

"My name is Lisa, which I suspect that you already know." She said, "I have seen you around the gym. I try to get there when there isn't a lot of people. I like my solitude. That also stops guys from hitting on me, but it can be difficult to find a spotter."

"I agree. Work changed my shift, so I had to work in the later times to get my workout in." I said.

"I'm glad you did, I have been watching you and your routine as well. You like to work on the chest area as well as the legs. This seems to keep your ass in shape." She said smiling.

"Thank you. I see that you're doing the same and the same weight level. Are you trying to bulk up?"

"No, I had some surgery done and need to get the muscles back in shape. Working out seems to be the best way to get them stronger."

She flexed a bit and the muscles were defined very well. "Looks like you are doing great."

"Thank you. The only problem I have is that after a good work out I get horny, which can be embarrassing." She smiled.

I thought about this for a bit, I had heard that people do get aroused when working out. I had to admit that I too had feelings like this. "It does happen. You get the blood moving around and you will feel something." I responded.

"Good let's leave I'm horny as hell." Lisa said taking my arm.

She was stronger than I thought and almost lifted me up out of the chair on her own. I stood following her out. She didn't live far from the gym. We walked to her place. Her apartment was a large two bedroom/two bath place. Once the door was closed, she turned to me and pinned me to the door, planting a kiss on me that almost sucked my fillings out.

"You're going to remember this night." She said with a smile.

I looked up at her and buried my face into her boobs. She pushed me into her harder, releasing a moan. We moved into the dining room and she lifted me on the table. She removed my shirt and unbuckled my jeans. She reached into my underwear and pulled out my already hardening cock.

"Oh, such a delicious sight. We must have been thinking the same thing at the gym." She smiled.

She sucked on the head and licked underneath the crown, cupping my balls as she took it into her mouth. She stroked the shaft down to the base. Moving her mouth down the length of my shaft. I felt the warmth of her mouth and moaned. My cock twitched in response and hardened. Her lips were like velvet on my shaft.

I looked down watching her head bob up and down on my cock. Her hand moved up my chest and found a nipple. She pinched it hardening the nipple. I cupped her hand pushing into me.

"Oh, you know how to make a man feel good." I moaned.

"Your cock tastes wonderful. The pre-cum is so sweet," Taking me further into her mouth.

Watching her as she moved my cock further into her mouth, I felt her smile as she stroked my balls. Surprising me her hand move down to my ass. She pushed on the. She was watching my reaction, I smiled as if to say go ahead. She pushed a finger against the hole and moved it around in a circle moving slowly past the ring. I inhaled and held it as she moved in even more. She moved into where my prostrate was located and pushed down on the area. My cock responded by cumming hard into her mouth. My hips moved off the table making it go further in her throat.

"Oh my god! That was great." I moaned as loud as I could.

She took all the cum off my cock and said, "Thank you and now it is my turn to cum."

She moved up my body, kissing up to meet me face to face. She smiled, "But first I have something to tell you."

I looked at her with an expression of "Okay."

"I told you I was recovering from surgery. It was an intensive surgery and it is only half way done."

She took off her gym shirt, to show her boobs. They were round and large.

"You had breast implants, no big deal."

"That's not all." She smiled as she took her pants down.

I looked down and saw a large bulge in her panties. She stopped to see my reaction. My eyes showed the shock I was in. I looked up into her eyes and smiled nervously.

"You're a guy?"

"Well I am in transition, so I believe that I would be called a she-male or transgender. Are you turned off?"

"Not really, however now is not the time to discuss it. I am horny." I said.

She slid her panties down and a cock jumped out at attention. It was 9 inches and had a tilt to the left. She stroked it and moved forward. I placed a hand on her stomach and opened my mouth to accept her large cock. I could see pre-cum on the head. Smiling and moving forward she placed her cock head on my tongue. She let it sit there for a while and I closed my lips around the head and sucked on it.

Holding my head, she moved further inside my mouth. I took her shaft and I relaxed my muscles allowing her more access into my throat. She started a rhythm with her hips. I felt her cock twitching in the back of my throat. She increased her rhythm and was now fucking my face. Her hands on my head were holding my head steady as she moved in and out forcefully.

"Take that cock. It has been so long since I had a real blow job."

I took her cock in further and it hit the back of my throat. She came almost making me choke. It was almost too much as I took all she had to give. It tasted great. I pulled on her balls to slow down her stream of cum. Her head was back while she moaned, "Oh god! Take as much as I can give."

I cleaned her off using my tongue and kissed her cockhead. She was still semi-hard and still leaking cum. She handed me a towel and I wiped off my lips. I stood and kissed her as we moved to the couch holding each other.

We sat there for some time before one of us spoke.

"Would you like something to drink?" She smiled.

She went into the kitchen to bring in some wine and sat down so we could snuggle together. I couldn't keep my eyes off her cock. It wasn't limp but not semi-hard either, but it was still longer than mine. Turning my head, she kissed me, and our tongues explored our mouths.

"You have a great body Peter. Your cock is perfect, and I like it, please don't be self-conscious. Mine has always been this size and it has intimidated a lot of women as well as men."

"I think the whole thing was a shock to me. I have never been with a shemale before and I did enjoy it. I cannot wait for your cock in my ass, if you want it there."

"Oh, it'll be in there and yours in mine. I said you were going to remember this evening and the morning."

She got up and turned on some music. I watched her walk to the stereo; her ass was so perfect and inviting, I wanted my cock in it badly. The music was very soothing, she turned and reached out to me.

Taking her hands, I stood moving toward her. She embraced me, "Time for us to dance," she whispered in my ear.

As we danced, my hands went to her ass cheeks; hers went to my waist and moved down to the small of my back.

"I loved how you hold my ass. They feel great on my cheeks."

I kneaded those cheeks and pulled them apart a little. She kissed me again, almost like an encouragement for what I was doing. Her hands moved down my waist to my ass cheeks, she spread them as well. She was able to move into them and find my hole.

"OOH, OOH, OOOH, that feels good." I moaned.

"It's going to get better."

She turned me around and held me close. Her cock was in between my ass cheeks as we danced. I felt her breath on my ear as she nibbled it a little. Her hands were at my stomach as mine were interlaced with hers.

"You can a lot about a person dancing with them."

"I heard that too. I can tell now that you want to continue our night."

She moved her hands down to my hardening cock and started stroking it in time with the music. Her tongue went into my ear and explored the area. Her stroking became harder and she squeezed my member.

"What are you doing?" moaning I asked.

"Making you cum of course and then we're going to fuck."

At that I moved my ass against her cock so that it access my hole better. She stroked me harder and faster. I felt the cum rise in my shaft as pre-cum leaked out. My hips bucked, and I shot cum out forward. My legs buckled, and I almost collapsed, she held on to me.

"I will never let you fall." I heard in my ear. Moving my head around we kissed.

She wiped me down with the towel we used earlier. Taken my hand, we went into the bedroom. She pointed to the bed.

"Now get on all fours." She commanded.

I got into position, feeling her warmth behind me she spread my cheeks and a tongue flicked at the hole. She moved a finger around the ring massaging it, so it would relax. She pushed inside, I thought I heard a pop as her finger made its way inside. She moved it around to widen it a little.

"I think your ready now baby."

"Put it in. FUUUUUCCCKKKK ME!"

She moved and positioned her cock at the ring. I felt the cockhead as she slowly went inside, it felt like a tree trunk was being pushed inside me. I relaxed and as she made her way inside. She held it there for a little bit.

"Just letting you get used to it. Remember this when it's my turn."

She then found a rhythm, thrusted back and forth in me. I moaned in time with her thrusting. She picked up the pace, hearing her grunt as she thrusted forward was a turn on believe or not.

"I going to cum now."

One final grunt and thrust, I felt the cum in my ass and as she pulled out it went up my back. We both fell forward on the bed, she was on top of me.

"OOH, OOH, OOOH that's a tight and fuckable ass." She said.

"My ass is still spasming from your log."

"I know, it will stop soon."

We moved to face each other, tongues exploring and cocks dripping. She smiled and kissed my nose.

"Time for sleep. We both need the rest and recharge." Sleepily she said.

"Tomorrow, I do the fucking."

"Right! I need to place my cock somewhere warm, it helps me sleep. Tomorrow evening I'm throwing a party with a few friends and we both will need to prepare."

I rolled over and her cock found its way into my ass cheeks. This is how I woke up.

JJ122964
JJ122964
145 Followers
Please rate this story
The author would appreciate your feedback.
  • COMMENTS
Anonymous
Our Comments Policy is available in the Lit FAQ
Post as:
Anonymous
5 Comments
azbisexualazbisexualabout 3 years ago
GREAT!!

This story was about perfect.

NOW.... we need chapter 2 and the party.

AnonymousAnonymousabout 6 years ago
Mmmm

Wow, erotic...from a bi virgin

FailedscoutFailedscoutabout 6 years ago
A Little Rough

The writing, detail and buildup were a little rough but did not take too much away from the story that you were trying to tell.

Try a little bit harder, pay closer attention to editing and I think you will soon be putting out 5 star stories.

Thank you for writing and posting here.

AnonymousAnonymousabout 6 years ago
A little strange

Pretty good but she's half way done with her surgery? I feel like english isn't your first language.

AnonymousAnonymousabout 6 years ago
Yeah

Needs an editor

But hot

I gave you 5 stars to encourage you

Share this Story

Similar Stories

Shemale Bar Straight guy goes into a shemale bar and is forever changed.in Transgender & Crossdressers
My Transgender Neighbor Mike falls for his blonde transgender neighbor, Caroline.in Transgender & Crossdressers
My New Trainer Workouts will never be quite the same.in Transgender & Crossdressers
My New GF has a Dick And I love every last inch of it.in Transgender & Crossdressers
Southern Hospitality Milfy seductress does all she can to score the boy next door.in Transgender & Crossdressers
More Stories