(Continued from Hustled at Pool)
I arrived at the bar and Dave was waiting for me with a beer. I walked up and took it from him as I handed him my keys. I started to take a drink when Dave asked how the game of pool turned out.
“Well, let’s just say that we beat each other. I beat her and she beat me.” “We both suck, that is why it took so long.” I commented. I had to laugh to myself, because if he really knew what I meant by all that.
“By the way, here are your keys, before I forget. We cleaned up a little before leaving.” I added.
“Now, that is what I call a good friend. You really didn’t have to do that, but at the same time I greatly appreciate it.” He said.
We sat around drinking and talking about the old days of when we were carefree and somewhat wild in our teens. Before we knew it, it was closing time and they were kicking everyone out of the bar. Dave and I said our ‘Byes’ and headed off into different directions.
I started to pull out of the drive when I remembered that Tyssa wanted me to call her after I leave the bar. I pull out my phone and I dial her number. It being 2:15 AM, I was hoping that I was not waking her up from a sleep. The phone rang 3 times when I heard her voice on the other end.
“Hello Tyssa, I am sorry if I called at a bad time. I really didn’t expect to be closing down the bar.” “I hope I did not wake you.” I said.
“No, as a matter of fact I was just about to put in a movie and sit back and relax. I just couldn’t stop thinking about what we did.” She said.
“Me either. I don’t think that this day could ever be topped.” I added.
“Well, you have my address. Why don’t you come on by and watch a movie and see where that takes us.” Her voice was like silk.
“I can be there in say twenty minutes. Will that be ok?” I asked.
“Perfect. That gives me time to get the popcorn buttered.” She replied.
I hung up the phone and pulled out her address. I was closer to her place than what I had thought. As I drove I started reminiscing about how our pool game turned out. She had me wanting more of her and I couldn’t wait to get there.
I pulled into a parking spot just outside her apartment door and I checked myself out in the rear view mirror. Call me vain, but I really did want to look good for her. Just something about her wanted me to look more presentable than I usually had done. I got out and walked up to her door. I knocked and waited for her to answer.
She opened the door and said “Well hello there, stud.”
I could feel the redness flow across my face. This was the first time that I had blushed in a very long time. She stood there in a sheer red nightie with matching panties. I felt my cock come to life when I caught a glimpse of what she was wearing.
“I hope you didn’t miss me too much.” I said as she stepped aside and allowed me enter into her apartment.
As I walked in I looked around and I knew she had good taste. Her apartment was well decorated. It was a better place than mine. She had plush carpeting with matching furniture and drapes. The décor was fitting for a very classy lady and that she was. My place consisted of an old couch, 42” Flat Screen TV and a High End Stereo system other than that, I was a bachelor.
I walked over to the couch and I waited for her to join me before sitting down. She walked up to me and kissed me hard, but passionately on the mouth. I kissed her back and we began to explore each other’s mouths with our tongues.
When she finally broke from the kiss she said “Please have a seat. I have missed you and I have things planned for us to do for the night.”
“Really, I can hardly wait.” I said.
I sat down on the couch and I watched as she walked towards the kitchen. I watched as her ass swayed from side to side with each step she took. She was a vision of loveliness and I just couldn’t take my eyes off her.
“May I as what you have in store for us tonight?” I asked.
“Sure you can ask, but don’t expect an answer. I promise to make this a night we will both enjoy.” She said.
After a few minutes, she returned with a big bowl of popcorn, strawberries, whip cream, chocolate sauce and a bottle of wine.
“I thought you had me over to watch a movie.’ I said in a jokingly manner.
“Well, that is what the popcorn is for. As for the rest of this, let’s just say, it is for when you change your mind.” She shot back.
As she bent over to set everything on the coffee table, I couldn’t hold back after her comment of changing my mind. I dropped down behind her and I grabbed her hips and I planted the biggest and longest kiss on her ass. I mean right between the cheeks.
“Mm mm!! It looks like someone has changed their mind about movie time.” She said as she pushed back on my face.
I stopped long enough for a reply. “I can’t help it. You were all bent over presenting me with your ass, so I figured what the hell.”
“Good choice.” She said as she pushed her ass back into my face.
I ran my hands up her legs and to the front of her panties. I slowly started to pull them down to release her cock. I reached into her panties and I help her cock find its way free. I never stopped kissing her ass while reaching for her cock.
She pulled away and spun around saying. “We have all night and unless you have to work on a Saturday, I plan on making this go for as long as possible.”
As her cock stood erect only inches from my face, I looked up only to answer her back. “I never work on the weekends. Weekends are my time and as for work, lucky for me it only operating Monday thru Friday.”
“Good. You don’t know how happy I am to hear that you are all mine for tonight and into the day.” She said.
I was just about to lean in and take her cock into my mouth. I needed it. I wanted it. Before I could, she spun back around and walked off pulling her panties back up. She was torturing me and I know she knew it. I could tell by the way she walked away.
She looked over her shoulder and said “Wait right here, I will be right back.”
She disappeared into a room. I assumed it to be her bedroom or at least one of them anyways. What seemed like hours were actually only a few minutes. She comes walking out of the bedroom carrying a video camera mounted to a tripod. She looked over at me and she noticed my expression.
“This is strictly for you. You can do whatever you want to do with the card once we are done. I am not the type to use this as leverage.” She stated.
“I am sorry; I didn’t mean to come across as thinking that. I guess I am a little intimidated by you.” “What I mean by that is….” I started to say.
“You don’t know how your friends would react if they knew who and what I am.” She finished and continued. “We don’t have to use the camera; I will go put it away.”
“Please don’t. Let’s do this. I know that this is something that you want and besides, I would love to have a recording of you and me.” I said.
“As for my friends, you are right. I don’t know if I could stand the ridiculing from them at least right now. I will tell you this, if we continue seeing each other after tonight and I hope that we do. I promise that you will be introduced to my friends and ‘yes’ they will find out one day.” I continued.
“Are you sure you want to do this?” she asked.
“Yes” was all I said.
She walked over and set up the camera. She pointed it towards the couch and turned it on. She then walked over to me and stood in front of me. I stood up and I wrapped my arms around her. I pulled her in for a kiss as I began to run my hands up and down her back and across her ass.
She broke the kiss and began to unbuckle my pants. She knelt down and pulled my shirt up and began to kiss my stomach as she pushed my pants to the floor. My cock was rock hard and straining to get free from my boxers. I could hear myself begin to moan as she kissed my body.
“You like this don’t you?” she asked.
All I could do was moan and croak out a raspy ‘yes’.
She then pulled down my boxers and my cock sprang straight out. I stepped out of my pants and boxers and I took my shirt off. She pushed me back and down on the couch. She turned and reached for the chocolate sauce and whipped cream.
She then proceeded to pour a little sauce up and down my shaft and across my balls. Surprisingly it was not cold, but room temperature. She then added some whipped cream and turned to get a couple of strawberries. Instead of just placing them into the cream, she squeezed them and milked them of their juices. As for the remainder of the strawberries, they were spread across my balls and up the crack of my ass. I was in heaven.
“What about your couch, won’t all this make a mess and destroy it?” I caught myself asking.
“I am not worried about my couch. All I want to do is make this a night that you will never want to forget. I can always clean the couch.” “Just sit back and enjoy.” she replied.
I felt like an idiot for even saying something so trivial. That was soon washed away as soon as I felt her tongue run up the underside of my cock and up to the tip. I began to moan loudly as she continued to clean my cock expertly with her tongue.
“Your cock tastes so sweet. The chocolate, cream and strawberries just add to the flavor.” She said.
All I could do was lay back, roll my eyes to the back of my head and moan. Once she had my cock all clean, she took me into her mouth and slowly took the full length of my erect cock. Slowly she began to move her head up and down my shaft. It took everything I had to keep from blowing my wad right then and there.
I guess she could sense what I was doing because she stopped and looked up into my eyes and said. “Don’t hold back. Let go, because I will get your cock hard again and we will make a night of this.”
She went back to working on my cock and again just the feel of her soft warm mouth on my cock was just too much. I was fighting the urge to let loose. I was so out of it that I didn’t even realize that she had slipped her hand up under my ass. It wasn’t until I felt her shove her finger into my ass.
“OH FUCK!! I’M CUMMING!!” I screamed out.
That was when I exploded, it was the most intense orgasm I had ever had. She swallowed as I shot load after load of cum down her throat. When she let my cock slip out of her mouth, she wiped what little bit cum up that had slipped out the corner of her mouth.
“How was that? As if, I really have to ask.” She said.
I was still shaking from the orgasm that I just had and said. “I think you know just how good it was. That was the greatest experience I have ever had.”
I stood up on shaky legs and I pulled her up. I could still feel the strawberry remains in the crack of my ass, as well as what she had forced into my ass when she pushed her fingers into me. I didn’t care, I just pulled her into me and I kissed her. While I was kissing her I turned her around to where we ended up switching positions. It was my turn to make her happy.
I untied her nightie and I pushed it back across her shoulders and I let it fall to the floor. I moved in for another kiss and I began to squeeze her breasts. She moaned under our kiss. I then took each nipple and I gently pinched and pulled on them.
I broke from the kiss and I slowly started to move down her chest. I made sure to stop and tease, kiss and nibble each breast and nipple before continuing my way down. As I moved down to the edge of her panties, I noticed that her cock was rock hard and sticking straight up through the tiny elastic band that held them around her waist.
I licked the tip and cleaned up the pre-cum that was sitting there. She flinched when my tongue slipped inside her pee hole. It was the warmest, sweetest and saltiest taste. She seemed to taste so much better than the first time I tasted her.
“Oh my!” She gasped.
I didn’t even stop to acknowledge the comment. I pulled her panties down and allowed her to step out of them. I stood up and I began to kiss her again. I stopped and looked her in the eyes and said “Tyssa, I know that I said someday I would want you to take my virgin ass. Well, after the orgasm you just gave me…….”
I didn’t even need to finish the sentence before she asked. “Are you sure? Is this what you really want? This is only a few hours from when you first found out about true me.”
“I know. It’s just after all of the care that you gave to me and the orgasm I just had. I feel that even though you truly are my first shemale………… “Yes, this is what I want and I want you to be my first, my first at everything.” I said.
“I don’t know what to say to that, Bill.” “Let me go and get some lube.” She said.
“No, let me take care of that for you.” I said as I dropped to my knees and I began the sloppiest blow job ever.
Once her cock was well lubed with my saliva I stopped and pushed her back on the couch. I stood up and turned and presented my ass to her. She pulled me back and guided her cock to the entrance of my ass. Before proceeding she asked one more time. “Are you sure you want to do this tonight?”
“I have never been more certain than I am now.” I replied.
With that she pulled me down onto her cock. “Just relax.” She said as she continued to pull me down.
I relaxed just a bit and that was all she needed to break through my anal barrier. I felt the head of her cock slip in and she stopped and held me there so that my ass could get the feel of her intruding cock. I had clinched my teeth and held back from screaming out. Again I relaxed and I felt more of her 8.5” cock enter me. Each time I took more and more of her into me the more pain I felt, but that subsided quickly. With a couple more tries she was buried full length inside my ass. I began to raise and lower myself onto her cock. Slowly picking up the tempo, it wasn’t long before I was riding her cock like a sex starved addict.
I began to moan with each thrust. My ass slapping on her thighs as her cock slammed into my ass. She began to moan herself. “Bill!” “Bill!”
She was trying to tell me she was getting close, but I was in another world as I rode her cock. I didn’t hear her say that she was going to cum. I didn’t even hear her to tell me to get up so that she could cum across my ass. Instead, I rode her until she just reached up, grabbed my hips and forced her cock as deep into my ass as she could.
“FUCK BILL!! I tried to stop you, but…….. I’M CUMMING IN YOU!”
I felt the head of her cock expand and as it erupted deep inside me that was when I felt fulfilled for the first time in my life.
“Yes!! I feel you cumming! It feels so good. I never thought it could feel so good. I mean so great.” I moaned.
Once her cock softened she helped me to rise up so that it could spring free from my ass. We got up and we kissed once more. It just seemed that each time we kissed the passion rose to a whole new level. She led me into the bathroom where we cleaned up and continued until the sun broke the horizon. We lay on her bed spooning each other. Finally she turned to face me and said. “Bill, I want to introduce you to my friends later tonight. That is if you want to.”
I kissed the back of her head and I scooted closer into her and said “I would love to meet your friends and I have decided that I want to introduce you to my friends, too.”
With that we both fell fast asleep.
If you like this continuation, I hope you will like Part 3. Tyssa’s Closest Friends.
Sorry so long and boring. Just want to make it as believable as I can. I hope that it is to all the readers liking.
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with this note attached, it has been posted without my permission.
<a href="https://www.lushstories.com/stories/trans/tyssas-place-part-2.aspx">Tyssa’s Place - Part 2</a>