Shemale Suprise

It was a Saturday night and I was chatting up this girl at my favorite bar. Her name was Heather and she had short light brown hair. She was cute, big in general, big boobs and a big ***, but she wasn’t pudgy, and in fact she had a very athletic body. She wore a short white miniskirt with a dark tank top and pink fishnet type top over it.

We had really hit it off, she was in her last year of college where I had graduated last year, and she was majoring in Ancient history, just like I did.

She kept giving me suggestive looks and body language, so after a few drinks I invited her back to my place. She agreed and I took her to my decent sized apartment in the suburbs of Denver. It was a simple living/dining/kitchen area and a hallway with two bedrooms and a bathroom. My dad owns the apartment and he leases it to me at a discount rate.

I welcomed Heather into my apartment with a flourish of my arms.

"Wow Matt, nice apartment" She sat on the couch while I made us another drink. We sat and talked for another 5 minutes, slowly leaning closer and closer to each other until I finally went in for the kiss. We made out and I fondled her boobs while she massaged my **** through my pants. She broke the kiss and slid down between my legs, unzipping my jeans as she went. She pulled my hard 8 inch **** out of my boxers and gently licked the tip. She licked my entire ****, coating it in saliva. The she stood up, bent over, pulled up her skirt and told me to **** her ***.

I couldn’t believe it. I usually had to date a girl for a long time before we had anal, but here she wanted anal first. I obliged and positioned myself at her rear entrance. I started slow but she told me to go faster and herder. I did. I was really getting into it now. I grabbed her **** and fondled them while I ****** her ***. After about 10 minutes I came in her ***, I was tired. As I tried to sit down, she pulled me to the bedroom. She pulled my shirt off me.

"Have you ever had a rim job?" she asked me.

"No I can’t say that j has. “I replied. She smiled and directed me to stand spread eagle at the foot of the bed and bend over it. I did so and j felt her mouth at the entrance to my ***. I felt her tying my feet to the bed posts but I didn’t care. I was tired from the *******, and this rim job was amazing. Suddenly she stopped. She walked around to my front and tied my hands to the front posts, this struck me as odd, so when she had returned to behind me I looked back to see her removing her skirt. What I saw stunned me into silence.

She had a ****. Not just some tiny little thing, no she was at least 10 inches.

"Now you know my secret. Will you let me **** you in the ***? Not that you can stop me of course, but I promise ill start slowly. And I’ll give you the best ******* of your life after."

I was still so shocked that all I could do was nod. I felt the tip at my *** she slowly pushed it in. "ahhhhh!" I screamed, but she didn’t slow down, in fact, I think she sped up. I cried out for her to slow down, but she just went harder every time I said something. Pretty soon she was going all out, ******* like there was no tomorrow. I was almost in tears from the pain. Finally she pulled out; I breathed a sigh of relief until I looked up and saw her aiming her rock hard **** at my face. I opened my mouth to yell at het but she just stuck her **** in my mouth. She groaned as she came.

My eyes widened as my mouth and throat was completely filled up with her ***. I swallowed all that I could. She pulled out and shot her last couple of spurts onto my face. I coughed and some of her *** dribbled down my chin. She laughed and grabbed her phone. She snapped a picture of my face. She walked around behind me and spread my *** cheeks and snapped another picture. She snapped pictures from several angles.

"Tell you what, if you walk from here to my apartment, only 10 blocks away, when aw get there, you can do anything you want with me, humiliate me, **** me, have me **** you again, anything ".

"I don't like that deal, ill decline it." I said.

"I'm afraid you can’t, because if you do decline it, I will simply leave you tied up, and I will **** you again, and k can go so much harder than what I’ve already done. I will coat your face, ***, and back in ***, then I will take pictures of it, and then send them to everyone in your contact list. Is that what you want? To be a laughing stock?"

"Do your worst." I replied, I was petrified of just going outside like this, I might see someone I know.

"Suit yourself. But remember, you can take the deal at any time tonight, before or after I’ve humiliated you." She was already hard again. She lined up at my *** and shoved in with huge force. I cried out and she just started pumping away. This time she pounded at me, but also pulled my hips towards her every time she thrust, increasing the force behind her thrusts. I screamed in pain and begged her to stop, but she didn't. It took nearly 10 minutes of the most forceful tucking ever to make her *** again. She went to my front and held my face, then hacked herself of onto my face. If I was covered before, I was plastered in *** this time.

She snapped more pictures, and then stroked herself back to hardness; it was unreal how much this girl could ****.

"Alright! I’ll take the deal. I’ll walk to your apartment “I said dejectedly.

She smiled, untied me, gave me a button up shirt and my pants, waited until I was dressed, and then thrust me out the door.

I was like a deer in headlights, but looking around, I didn't see anyone. I glanced at a clock in the hallway and saw that it was almost 1 in the morning. No one was around.

"Oh by the way, one last part to our deal, you have to do anything anyone asks you to do while were walking. Ok?" Without waiting for a response she pushed me down the hall towards the elevator.

There was no one on duty down in the lobby. So I walked out onto the street. Immediately I saw very attractive blonde woman walking down the street towards us. She was close enough to see the *** on my face and said: "well how'd you get *** on your face, I don't see a guy with you, only that pretty girl." Heather proudly said "it’s my ***, his *** milked it out of me." My face was beet red under the white coating.

"Hey, want to do that for me?" She lifted her skirt to reveal a large bulge in her panties

"Sure he would!" heather said enthusiastically. She practically ripped my pants off me, bent me over and spread my legs. I felt a tip at my *** and moaned when she shoved in me. It took her only 5 minutes to ***. She didn't give any warning; she just suddenly exploded in my ***.

"Ahh that was nice, would you be kind enough to clean me off?" Heather again spun me around and forced me to my knees. I opened my mouth and the blonde shoved her **** in my mouth. She was extremely attractive, huge boobs, tight curves, and quite a large ****. I wasn't so thrilled about the last part though. Now she was getting angry because I wasn't sucking her ****.

"Be a good little **** sucker and do it properly Kr you will walk the rest of the way without your clothes." This frightened me into action and I tried to replicate what girls had always done with me. Use my tongue to tickle the underside of her shaft, lick the head, but I never tried to deep throat her, which was obviously annoying her.

"**** sucker, if you don't take my **** balls deep, I'm taking all your clothes with me when I leave."

I tried and I tried, but I couldn't take her entire **** down my throat.

She groaned and came again, pulling out so it spilled onto my face.

"Tough luck **** sucker." She picked up my panes and boxers from the ground and held out her hand expectantly. I slowly unbuttoned my shirt and handed it to her. Holy ****. How did I get myself into this?

The blonde walked away and heather told me to keep going. It took us nearly an hour to cross the ten blocks, which normally would take about 5 minutes. The reason was we kept running into very attractive shemales who wanted either my *** or my mouth. By the time we got to her apartment, I had sucked and ****** almost 20 girls.

"Ahh, home sweet home. She said as she walked into the lobby. I followed and stopped when I saw what was inside. my eyes bulged. She in the lobby was apparently a party. 30 very attractive girls, aged 20 to 30 were all lounging around talking. Everyone stopped what they were doing and started at me. I saw several of them rubbing bulges on their pants or skirts.

Suddenly a laugh rang out. "Heather! How nice of you to bring me a male ********. I would have preferred if he was still clothed, and not covered in your ***. But I’ll take him anyway." A small redhead pushed her way up to us and cupped my balls.

I turned to heather and whispered: "no, we made it to your building; I don't have to do anything." She whispered right back "were not at my apartment yet, so, yes you do. Sorry bud, I didn't know they would still be here."

The red head looked me over, then forced me on my knees, pulled up her tight skirt, and said "suck".

I held her huge 12' **** in my hand and stared at it.

Heather nudged my head. I gently licked the shaft. Then placed the head in my mouth and sucked. The redhead was growing impatient for the real ******* to. Start, I delayed still, enjoying he power I had, until she grabbed the back of my head and started pumping. This was the first time all night that I had gotten face ******, and I wasn't enjoying it. She seemed determined to force her entire **** down my throat. The biggest **** I had seen before hers was only 10' in heather. I couldn't even fit hers down. No way could I get 12.

"I *** when I want and I are not ******* until my entire **** has been down your throat and fit entirely in your ***. And then, when I ***, you will swallow it all down, or else well keep you here, for as long as we like" The redhead ground out. I tried to push her away from me but to no avail. I was weak and tired from my night of *******. After almost 15 minutes of trying, I had taken 11 inches and was still struggling to get the last one.

"I'm not gonna stop till your nose hits my body." The redhead yelled. It took almost 10 minutes, but I did it. My nose touched her body. She held me there, enjoying the sight of a grown man choking on her 12 inch ****. She pulled me off and spun me around. "Now let’s see how your *** is."

I cannot even describe how painful that first thrust was. She pounded my *** like there was no tomorrow, she kept at it for almost 10 minutes. She pulled out, spun me again, and shoved her **** back down my throat; she shot jet after jet of *** down my throat. My stomach started to fill up quick and the *** was bubbling up my throat. When the redhead pulled out I almost threw up all the *** in my stomach.

"Make it last girls!" The redhead yelled. All 30 of then rushed at me, pulling me further into the room.

For the next hour I sucked, ******, and stroked every single one of them. I saw big *****, small, thin, fat, black, white, Hispanic, any type of **** you can imagine.

When the last girl had ***. Heather took my arm and took me to the elevator. I could barely walk because I was so coated in *** and my *** was so sore.

It was almost 4 in the morning now and I was a couple of doors from safety. The elevator doors opened and two more girls were standing there waiting. I groaned but the girls just ignored my appearance and stepped aside so we could exit. I practically ran to heather's door. Heather directed me to the shower and I gladly stepped under the steamy water. It felt so good to wash all the *** and dirt off my body.

The curtain rustled and I felt hands running down my back. I turned and heather leaned up and kissed me deeply.

"I'm sorry; I didn't realize the party was still going on. It normally doesn't get so out of hand." She said apologetically. She grabbed some soap and gently massaged it into my chest and arms.

"You've done this before?" I asked.

"Oh yes, multiple times. Normally I can only get 4 or 5 girls to help. Everyone in this complex is a shemales. Almost a hundred girls." Her hands were slowly working down my body.

"And you just **** and humiliate all the guys?"

"Yeah. But every guy has loved it so far. One actually asked to do it again." Her hands were massaging my **** and balls now.

"Oh really?" She slowly lowered herself down onto her knees. "No offense, but I dint that I could... ahaaaaa" heather took my entire **** down her throat in one try. She bobbed her head up and down, sucking like mad. She started fondling my balls again while sucking. She started focusing on just the head of my ****, licking around it, sucking on it, all while stroking the shaft.

The *******, coupled with the warm, relaxing shower and not ******* since I had penetrated heather, made for one of the biggest cumshots I’ve ever had in my life. Heather just held the head in her mouth and jacks me off into her mouth. When I was finished, she stood up and showed me all my *** in her mouth. She closed to swallow and showed me that it was all gone. I nearly fainted right there.

We both got out of the shower and dried off, neither of us put on any clothes before just falling into bed and falling asleep right away. My last though before I was out was: 'what the **** happened to me tonight?'

The end. Next, what happens when matt wakes up?
Creampieguy76 Creampieguy76
36-40, M
5 Responses Jan 5, 2013

This is a story on Literotica... just saying...

can I date Heather ?

if she agree's I will be glad

Lovely story and the party at Heathers place would be loads of fun no pun

Wow I loved it!!

Loved your story