Shemale Surprise Ch. 02

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Matt and Heather get to know each other.
1.8k words
4.47
106.7k
110

Part 2 of the 2 part series

Updated 10/07/2022
Created 11/26/2012
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I woke up to find myself staring at a nice ass hanging over my head. That ass belonged to heather, an extremely attractive shemale who tricked me into letting myself get gangbanged by a group of shemales. She then let me stay in her apartment, as my clothes had been stolen a long time ago. I then realized that I was being sucked off by heather. She had gotten on top of me in the 69 position, I guess hoping that when I awoke I would suck her cock too. I gently leaned forward and licked her large member from base to tip.

The owner of the cock twitched as my wet tongue made contact. I kept licking the underside of it when finally I slurped the head into my mouth and took the whole thing down my throat. I bobbed my head up and down, pulling it all out and then shoving it all right back in.

Heather got off me and put herself in a doggy style position next to me, head on a pillow, ass sticking up invitingly into the air. I obliged her and positioned my cock at the entrance to her ass. I pushed in hard and she moaned, I fucked her furiously for as long as I could before I felt I had to explode. I pulled out and heather quickly spun around took my cock in her mouth, I exploded and heather gulped down everything that I gave her.

I fell back on the bed, but I wasn't finished yet. Heather flipped me over and pulled my ass up into the same position she had been in. She pushed in every bit as hard as I did and I bit back a cry, my ass was still sore from the previous night of ass fuckings.

She pounded me for about as long as I had fucked her. I spun as quickly as I could and swallowed everything she gave me.

We both fell back onto the bed in each other's arms.

"I'm still sorry for what happened last night." She said. "That got way out of hand and I should have stopped it. But you look so cute with a cock in your ass." She smiled and gently grasped my cock. She slowly stroked it but I remained limp.

"What are we going to do about my clothes? Its broad daylight out now and I can't walk home completely naked." I told her.

"did you forget what I told you last night, every girl who fucked you last night, including the one who took you clothes, live in this building and are friends of mine. I can get your clothes back." She informed me.

We relaxed in bed for another 10 minutes before heather got up to go get my clothes. I got up and went to the kitchen to make breakfast. Heather retuned just as I finished with making eggs. I dressed as she sat and rubbed her hands in anticipation of my delicious looking breakfast.

We ate quickly and talked about what had happened last night and more about her building. IT seems she was one of the first to move into this building when it was built. The first person to move in was the redhead from last night, whose name I learned was Alli. Heather and Alli, along with two other girls, Janielle and Morgan, were considered to be the leaders of the building and everyone looked to them.

After breakfast we cleaned up and I announced that I would be leaving shortly. Heather told me she would walk me back to my apartment.

We left 5 minutes later. We got in the elevator and heather pressed the button for the lobby.

When we stepped into the lobby there were three women standing around, seemingly waiting for us.

"Ah heather good, you're just in time." It was the redhead from last night, Alli.

"In time for what?" Heather said, stepping protectively in front of me.

"To give Matt our numbers." Alli responded. I looked at the other two women. About the same height and weight, one had long brown hair while the other had blonde hair in a sort of butch cut. "We were talking and we feel that everything got out of hand last night. We would really like to give matt a chance to get to know us better before he condemns us as a bunch of Horny shemales."

I stepped around heather and walked right up to Alli. "You have the biggest cock I have ever seen, and you know how to use it. I would love to see you again." I opened my arms and Alli squealed with delight and gave me a huge hug. I had to ask the other two who was who and they told me. The long brown haired one was Janielle while the short blonde haired one was Morgan. They gave me little pieces of paper with their names and numbers on them. I promised that I would text them when I got home.

Heather and I left after that. It was a silent walk back to my apartment. I recognized several places where I had been stopped and fucked going the opposite way the previous night.

We reached my apartment in a scant 5 minutes. A lot better than the hour it had taken last night. When we reached my building heather turned to me and gave me a long lingering kiss. "Again, I'm sorry about last night. I hope I will see you again, my numbers already in your phone." I didn't know how she pulled that off, since my phone was still in my apartment. Then she turned and left, walking back towards her apartment. I watched her go lustfully, wanting her and her cock back. I went inside and continued on with my normal routine.

The next day I called up heather.

"Hello?" Came the sultry voice from the speaker.

"Hey baby, it's me. I was wondering if you wanted to go out to dinner and a movie with me tonight. I've got tomorrow and Tuesday off so we got options if tonight doesn't work."

"Yay! I'm so happy you called! I couldn't stop thinking about you last night. J would love to go out with you tonight." She squealed

"Great, I'll pick you up at 6. I've got a great restaurant in mind."

"Sounds great see you there, and make sure you don't wear any underwear" she breathed.

I spent the rest of the day fantasizing about heather. When 6 finally came around I was ready. I was in a red button up with a black blazer and black pants. I texted heather to tell her I had arrived and was waiting in the car.

I gasped as I caught sight of her. Her hair was tied back in a bun behind her head with a few strands framing her face. She was wearing a black sleeveless dress that was so tight her ample boobs threatened to pop out. The dress only reached her mid-thigh, so there was quite a bit of leg showing.

As she got in the car I told her she look amazing and j drove her to the restaurant.

"Are you sure this place is open? It looked closed" heather said as we pulled up.

"I'm positive" I told her. I parked right out front and we walked in.

It was deserted inside except for us and the wait staff. We were seated at the best table that was decorated beautify with flowers and candles.

"How did you arrange all this? This is a really fancy restaurant and you rented out the whole thing!"

"Well it's very simple, I work here." I told her.

We enjoyed one of the best meals ever, she told me all about her life, how she works as a personal assistant for a lawyer and that she doesn't tell most people she's a transsexual, even her coworkers don't know. I told her about working at the restaurant and how I had decided to move out here from my hometown.

We finished our meal and my friend John came over. "Any dessert for the lovely couple?" He asked.

"Hmm, what is Adam making?" Adam was the dessert chef.

"He really wants to make an ice cream Sunday."

"Then let's go with th-ahhhhht" heather's foot was nudging my member through my pants. John looked at me oddly and left.

Heather continued to play with my junk until dessert arrived. Her face lit up at the sight of the massive bowl of ice cream, chocolate sauce, whipped cream and cherries.

When we were finished I called John over and he presented us with the bill, which was about half of what I thought I should be.

"It's a favor; you'll have to repay it later" John told me when I asked about it.

Heather and I left after that and went back to my place. As soon as my door clothes we were practically tearing the clothes off each other. I pulled heather's dress down so I could get at her tits. I grabbed and squeezed them before licking and sucking on the nipples. She moaned and ran her hand through my hair.

I moved down her body until I reached her cock. I pulled the dress up to her waist and sucked the half hard member into my mouth. It quickly grew to full hardness and I got up and bent over the couch. She came up floss behind me and positioned herself at my entrance.

"You know what I like about you? You never complain, no matter how hard I push in!" With that she rammed her full length up my ass. I gasped. I forgot just hoe big she was. She continued pounding my ass until I screamed out loud. She pulled out and flipped me around. She shoved her cock in my mouth and i eagerly sucked on it, glad for the break from ass fucking. I took her cock deep in my throat, touching her stomach with my nose and licking her balls. Suddenly she grabbed the back of my head and held me there, while simultaneously pinching my nose. I couldn't breathe. She held me there for a minute, with ne struggling to get away the whole time.

When she finally released me I gasped and turned away from her. As I did, she firmly grabbed my waist and hauled me up so I was completely bent over, at which point she brutally fucked my sore ass. She went for another 5 minutes before she pulled out, spun me around, and stuck her cock back down my throat. At this point she came explosively, shooting it straight down my throat and into my stomach. She pulled out before she was done cumming, filling my mouth and coating my face.

"Ahh, good boy. That felt nice, sorry about how rough I got, it's a habit."

"No need to apologize" I gasped, "I actually kind of liked it."

"Oh good!" She cried.

"But I'm too sore to fuck you, let's just go to bed and ill fuck you in the morning?" I said

"Sounds good to me! And just so you know, I have Monday and Tuesday off work too..."

The end.

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RodimusMikeRodimusMike10 months ago
Heather and the Gurls.

As Dom'ish as Heather and the Girls were and are,they are all Sweet Shemales,even if they are rough when having sex with their boytoy,but otherwise when not in a sexual situation Heather seems like a sweet shemale girl,but very playful and fun to be around.

Also Heather seems shy and timid sometimes probably because she can't fully comeout as a Shemale,but with Matt basically supporting Heather and the Girls they can live a somewhat fun lives regardless of the stigma people have against girls like Heather.But while on the subject I wish all of society would accept TG's and Shemales and TS's for who they are,they are not so different than anyone else even if they have a cock or not.

AnonymousAnonymousover 1 year ago

His coworkers John and Adam ask Matt to hook them up with heather,. Heather agrees but only if they agree to take her and a friend out together. They arrive to pick them up and the friend is actually Matt dressed like a sissy looking very hot, the boys don’t realize it’s him. Eventually they return to heather apartment and they get tied up, but Matt and heather. At some point heathers friends show up “unexpectedly” and join the fun.

pillow996pillow996over 1 year ago

loved it! my fantasy

sissyboi69Aricsissyboi69Aricabout 2 years ago

I think I would love shemale cock. Loved the story

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Shemale Surprise Previous Part

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