I woke up later than morning and Tyssa was already up and in the kitchen. I climbed out of bed and walked into the kitchen. She was busy preparing coffee, so I walked up behind her and I wrapped my arms around her and hugged her tight. I kissed the back of her neck and said “Good morning.”
“Good morning, would you like a cup of coffee?” she asked.
“I sure would and is it ok if I make myself at home?” I replied back.
She looked over her shoulder and said, “It would make me happy if you would. I think you have earned it. Besides, last night was great.”
“I never thought I could ever feel the way I do when I am with you. I really enjoy being with you,” I said.
She turned around and faced me. I leaned in for a kiss. She pulled me into her and we began kissing each other passionately. Our tongues inter twined with one another, exploring each other’s mouths. I ran my hands down her back and to her tight ass. I squeezed her tightly. When we broke from our kiss she looked at me and asked, “Were you serious about meeting my friends later tonight?”
“Of course I was serious. I was also serious about you meeting my friends too,” I replied.
She turned back to the coffee pot and pulled down a couple of mugs that were hanging under the cabinet. As she began to pour the coffee, I knelt down and kissed her ass. I stood back up and said, “Tyssa, I have to go home for a bit. I have to tend to my dog. She needs to be fed and watered. I can be back here in a couple of hours.”
“OK, that sounds like a plan. I have to run a few errands, so I guess that will work to both our advantage. Call me when you are done and ready to head back. Maybe we can meet up for lunch,” she said as she finished pouring our coffee.
We sat down at the table and drank our coffee and chatted a bit. When we finished we both went back into the room and got dressed. We kissed once more and we both headed out in opposite directions. I headed home as fast as I could because I wanted so bad to be with Tyssa as fast as possible. She had an effect on me that I never would have thought could happen to me. I was engrossed in her beauty and the way she treated me. I wanted to be with her even though we have only been together for the past couple of days.
I finished feeding, watering and walking my dog. I contacted my neighbor and asked if he would have his kids keep an eye out on my dog for the next week. I had lied and said that I had some business to tend to out of town. He had told me not to worry and he would make sure that my dog was taken care of. I said my thanks and headed off. I pulled out my phone and made contact with Tyssa. We made plans to meet at ‘Kirby’s Bar and Grill’ for lunch. I arrived a few minutes before her and got a table. I waited for her arrival.
“Sorry I am late. I got hung up in long lines at the register," she said as she approached the table.
“You’re not late. You are right on time by my watch,” I replied back.
The waiter came up and took our order. After he walked away we began to discuss our plans for tonight. Tyssa had already called a couple of her friends and had made plans for them come by later tonight. Tysssa had told me their names were Shonda and Kelli. She had also explained that she wanted to try something new tonight and wanted to make sure that I was up for her surprise for me.
“I get to meet your friends and now you have a surprise for me? I can hardly wait to see what that might be. Do I get any hints as to what the surprise might be?” I asked.
She glared at me but not in a mad kind of way, but a teasing way and said, “Now what kind of surprise would it be if I said anything about it? You will just have to wait and see. I just hope that you like what I have set up.”
“If it is anything like the past couple of days of being with you, then I know I will like it,” I replied back.
Our lunch arrived and we both ate and had some more small talk. I didn’t ask about or bring up tonight’s surprise anymore. After we finished lunch I walked her to her car and kissed her good bye. I had informed her that I would be over in about an hour and that I had a quick stop that I had to get done. She had said "ok" and she drove off. I in turn walked to my car and drove off.
I had finished what I had to do and I headed to Tyssa’s place. I was so looking forward to being with her again. While away from her I felt empty and queasy in my stomach. Something I never felt before. Tyssa definitely had a hold on me like no other and I just wanted to be with her. I pulled up and parked my car. I walked to her door and before I could even knock she had opened the door.
“I saw you pull up and I couldn’t wait for you knock. Get in here!” she said as she pulled me into her apartment.
“Is everything OK? What’s wrong?” I spouted out. Her actions led me to believe that something was wrong.
“Nothing is wrong. Everything is great now," she said as she pushed me to the couch and began to fight to get my pants off.
Before I could protest she had my hard cock out and in her mouth sucking me like she was on a mission. I threw my head back and moaned out loud. The way she was sucking my cock had me over the edge and shooting my load down her throat faster than I could have ever imagined.
“Mmmmmm!! I really needed that. I was wanting to climb under the table at lunch, but I knew I had to control myself until you get here," she said as she wiped her mouth.
I looked up at her and said, “I know exactly what you mean. I feel so empty when I am away from you. I know we only just met, but there is just something about you that……..”
I jumped up, scooped her into my arms and carried her off to bed without finishing my sentence. I laid her down and began to remove her clothing. Once she was completely naked, I began my work on her. I started at her feet and I made sure to suck each toe, kissing the soles of her feet, up each calves, kissing my way up each inner thigh and up to the prize I was so wanting. I lifted her legs up and spread her ass cheeks and I began to work my tongue in and around her asshole. All she could do was moan as I continued my work on her. I tongue fucked her ass for a few minutes and then I began to lick and suck on her balls. I worked my tongue up the underside of her cock until I reach her pulsating head. I took her into my mouth and I began to give her a slow and sensual blow job.
“What has come over…ugh… you Bill?” she managed to spurt out.
“Ssssssshh..." was the only reply she got from me as I went back to sucking her cock.
I made sure to take my time because I wanted her to want me that much more when I finished what I started. She moaned loudly and I knew she was getting close so I took all that I could down my throat and began to suck her with passion. I felt as her cock head expanded and I knew what was going to happen. She grabbed my head and lifted her hips, forcing her cock a little deeper down my throat.
“OH FUCK!! BILL, I’M CUMMING!! MY GOD, I’M CUMMING!!” she managed to scream out as her hot load shot to the back of my throat.
That was the first time I managed to swallow everything she gave me without losing a single drop. I slowly let her cock slip out from between my lips and I started kissing my way up her body until we were in yet another passionate kiss. When we finally broke our kiss, I lifted up and looked into her eyes. She was nearly in tears and I thought I had did something wrong. So I asked, “Did I do something wrong? Did I hurt you?”
She looked back at me and replied, “No, you did not hurt me. That was the…… I mean… What you just did… I just ……”
“I told you that I have never felt this way before. Being with you is the best thing in my life. When we are apart…. I feel empty,” I said before she could finish whatever it was she was trying to say.
“I feel the same way," she said.
I got up and I walked over to my jacket and I pulled a small box from my jacket pocket. I walked back over to Tyssa and I opened it up for her to see. “I got this for you. I want to show you what you mean to me,” I said.
She gazed into the box and she began to cry as she pulled out the diamond necklace I had bought for her. I showed her the inscription on the other side and it read, ‘You are my world and my life.’
“I hope that I am not moving too fast here. This is how I honestly feel about you,” I said.
“I love it. I feel the same way," she said between sniffles.
She looked over at the clock and noticed the time. We both got up and began to get ready for her friends to arrive. We showered, cleaned up the apartment and got dinner ready. An hour later there was a knock on the door. Tyssa went over and opened the door and in walked Shonda and Kelli.
Shonda was an ebony goddess. She was about 6’2”, long black hair that was about to the middle of her back, long succulent legs, curves in all the right places and breasts that any man would die to put his face between. She was wearing a white blouse and a grey mini skirt. She walked over as Tyssa was introducing her to me. I extended my hand to her in which she just pushed away as she leaned in and kissed me on my mouth. I was caught off by that and I shot a look over to Tyssa.
“Shonda is like that. It’s ok if you want to kiss her back. Actually I insist," was all she said.
Shonda leaned in again and we locked lips and began to kiss, exploring each other’s mouths with our tongues. We broke our kiss and Shonda walked over and sat down on the couch. My head was swimming with what was just happening and I was really beginning to wonder just what surprise Tyssa had for me.
Next I was introduced to Kelli. Kelli was about 5’7”, shoulder length brown hair, nice supple tits and an ass to die for as well. She was wearing the tightest jeans I have ever seen anyone wear and a light blue semi-see through top. She was not wearing a bra and her nipples were sticking out and erect. I am guessing from watching Shonda and I kiss the way we did. I looked over to Tyssa again and all she did was wink. I took that as a sign that Kelli and I would also perform the same as Shonda and I had just did. I was correct. Kelli walked up to me, grabbed me and pulled me into her, kissing me with more ferocity than Shonda did. She had grabbed my ass and squeezed, causing my mouth to gasp, at which she shoved her tongue down my throat. Once our greeting was complete she too walked over and sat down on the couch.
I walked over to Tyssa and put my arm around her and we started walking over to join Shonda and Kelli. I leaned in and whispered, “Will it be like this with all your friends?”
“Only with Shonda and Kelli,” she whispered back.
We sat down and Tyssa immediately showed Shonda and Kelli the necklace I had given to her. Shonda and Kelli both let out an "Aaawwwww" at the same time. Then they turned and looked in my direction. I could feel the blood rush to my head as I began to blush.
“Isn’t he something?” Tyssa asked.
“He sure is," is all Kelli was able to say.
“You better not lose this one,” Shonda spurted out.
We sat there talking and sipping down drinks. Tyssa finally got up and announced that dinner was ready. We all got up and walked over to the table and sat down. We ate dinner and small talk up until the desert was brought out. After we finished, we walked back into the living room had a few more drinks. Tyssa then looked over to me and asked if I was ready for the surprise she had planned for me. All I could say was "yes."
She rose and took me by the hand and led me back into the bedroom. She looked at me and asked, “Do you trust me, Bill?”
“Of course I trust you,” I replied.
“I want this to be another night you will never forget. This is something I have always wanted to do and being with you…….. I think I can," she said.
“You tell me what you want to do and I will do as you wish. I am yours, that is if you will have me,” I stammered out.
Tyssa started to strip me of my clothing and she guided me onto the bed. I let her do whatever it was she wanted to do to me. I ended up being positioned across the bed on all fours with my ass up in the air. She had taken velvet cords and tied my hands and feet to the four corners of the bed. She leaned in and whispered, “If you want to stop, all you have to do is pull on your restraints and they will easily break. That will be my signal to stop and call off ‘our’ surprise.” She put a little emphasis on ‘Our’.
I looked up at her and said, “I am yours and I look forward to whatever you have planned for me.”
She walked out of the room and returned a short time later with Shonda and Kelli in tow. Shonda walked up in front of me and proceeded to get undressed. She removed her blouse and her bra. Her tits sprang free and they were even bigger than what they had appeared all bound up in her bra. She removed her skirt and stood up. That was when I saw that she too was a shemale. My heart began to beat faster and my cock sprang to life. It wasn’t until Shonda removed her panties and stood back up that my eyes nearly popped out of my head. Shonda had the biggest cock I had ever seen on a shemale (Porno Pictures that is). She wasn’t even hard yet and it was at least 11” long and as thick as my wrist.
“I think your man likes what he sees," she said as she noticed my rock hard cock. I felt inadequate compared to her.
She walked away and was replaced by Kelli whose turn it was to put on a show for me next. She had ample tits and when she stood up after removing her jeans, her cock shot straight out. It was about 9” but not as thick as Tyssa’s cock. She walked towards me and placed her cock up against my lips. I kissed the tip and then stuck out my tongue to sample the pre-cum that formed up. Kelli pushed her hips toward my mouth and I opened up to accept her cock. While Kelli fucked my face I heard Tyssa and Shonda behind me kissing and rubbing each other.
“Shall we get him ready?” I heard Tyssa ask Shonda.
“Not yet. I want to see what he can really do," she replied. That was when she came around, moved Kelli aside and then placed her cock in front of me.
“I know that I am so much bigger than these two, but I promise I will be gentle with you." This was all Shonda said as she slowly pushed her cock into my over stretched mouth.
I could feel her cock grow as she slowly worked her cock deeper into my mouth. It had grown another 3” at least. She was hung like a fucking horse. I could hear Kelli and Tyssa talking with each other as Shonda slowly fed me more of her cock.
“He is taking her cock better than what we had expected and he hasn’t even broken his restraints,” Kelli said.
“I know. I really am surprised and just watching him take her cock has got me so fucking hard,” Tyssa said.
“Let’s get him prepared for a time of his life," Kelli said.
After hearing that last comment I felt Kelli and Tyssa kissing and licking my ass. Every once in a while they would slip their tongue inside my ass. Then their tongues were replaced by fingers and then after that a dildo. They worked the dildo in my ass and all I could do was moan while Shonda still fed me her cock.
“Ok, it is my turn now,” I heard Tyssa say as she pushed Shonda away. “Go back there and play with Kelli," she said, and at the same time she gave Shonda a wink.
Tyssa looked down at me and asked, “Do you like your surprise?”
“I wasn’t expecting anything like this, but yes, I am really enjoying your surprise. I look forward to whatever you may have for me,” I said.
Tyssa looked up at Shonda and Kelli and said, “I think he is now ready.”
I felt them remove the dildo that was buried in my ass. It slid out and all I could hear was a slight ‘pop’ as it broke free of my ass’s grip. That was when I felt the head of a cock being pushed against the entrance of my ass. I tried to look back to see whose cock was being pushed in when Tyssa grabbed my head and pushed her cock into my mouth. It felt as if my ass was being ripped apart and I tried to scream out but Tyssa’s cock kept me from doing just that. After some steady pressure I felt the head of a cock pop past the entrance. They stopped and waited for me to relax.
“That’s it baby. Relax. The pain will subside in a minute." This was what Tyssa whispered into my ear, all while feeding more of her cock into my mouth as a cock was being forced into my ass.
I relaxed as she kept whispering to me, then I felt the cock slip deeper inside of me. She would stop wait a minute for me to relax and then work more of her cock into me. Just by the way my ass was stretched out I knew it was Shonda shoving that monster cock into my depths. I pulled at the restraints but I made sure I didn’t break them. I wanted to continue with this. It was hurting me, but at the same time I was enjoying being filled with a cock like Shonda’s.
“Do you think he can handle all of your cock, Shonda?” I heard Kelli ask.
“He will be able to do more than that by the time I get the rest of it shoved in his ass," she replied.
“Well, I am tired of being left out.” That was all that Kelli said before slipping under me and taking my cock into her mouth.
I couldn’t believe what was happening to me. I had the girl I had fallen for face fucking me, Kelli sucking my cock and last but not least I had Shonda’s monster cock damn near buried in me. This was more than I could have ever imagined happen to me. I was definitely in a shemale heaven.
“Tyssa, I need you to get ready for the ‘coupe de grace’,” I heard Shonda say.
“I am ready whenever you are, on the count of three,” Tyssa said.
That was when I felt Shonda pull back and in one quick thrust she buried her cock in my stretched out ass. At the same time she shoved her cock into me; Tyssa had pulled back and shoved her cock deep down my throat. The pain was so much that I was gagging and screaming all in the same breathe. Shonda just left her cock there for a minute while my ass slowly relaxed. Once my screams turned into moans, Shonda began to fuck my ass. Slowly and deliberately.
So here I am, one cock buried in my throat, one buried in my ass all the while both being worked in and out at a steady tempo. Then there was Kelli. She was slowly sucking my cock to an orgasm I knew would be soon. I felt like I was being squeezed from the front and back as Tyssa and Shonda both leaned in and began kissing each other. I felt my balls tighten up and Kelli began to suck my cock like there was no tomorrow. I let out a groan and I shot my load down her throat. My orgasm was so intense I just knew I was going to pass out, but I kept conscious through it all.
“Mmmmmm!! That was quiet a load you had just for me, Bill,” Kelli said as she climbed out from under me. “I think he is ready for the finale," she continued to say.
Tyssa grabbed my head and began to fuck my throat and I felt Shonda grab my hips and begin to pick up her pace as well. I moaned with each thrust from both. I felt Tyssa’s cock head expand and I opened my throat for what was about to be fed to me. I felt the first shots hit the back of my throat when at that same moment Shonda’s cock expanded and I felt her cum shoot deep inside my ass. Shonda grabbed my hips and forced her cock as deep as she could while exploding deep inside me. Both Shonda and Tyssa moaned as their loads were forced at both ends of my body.
As Tyssa’s cock slowly shrank she let it slip from between my lips. She bent down and kissed me. “I hope you liked this," she said.
I kissed her back and I felt Shonda slowly withdraw her cock from my now sore and stretched out ass. I could feel her cum slowly running out of my ass and down my thigh.
“I did. Thank you so much for introducing me to my wildest fantasy. I could never show you the love that you have just showed me, but I will try,” I said.
I looked over to Kelli and as she stood there with an erect cock and so desperately needing attention as well. I asked, “Are you ready for your finale?”
“It would be great if I could get some of what ya’ll just had," she said.
I broke free of the restraints and I jumped up. I grabbed Kelli and set her down on the bed. I climbed up between her legs and I proceeded to give her the same slow and sensual blow job that I had given to Tyssa earlier. She moaned with pleasure as I took the entire length of her cock down my throat. Within minutes, Kelli shot a massive load down my awaiting throat.
We all moved back into the living room and out foursome continued until early the next morning. Tyssa and I are having talks about her moving in with me and her giving up her apartment. In the meantime all four of us still get together once a week and we take turns at fucking and sucking each other off to massive orgasms.
Keep an eye out for Chapter 4. Tyssa moves in and meets my friends.
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”
“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.”
Chapter 1Truly a fantasy I would love to live out. (First Attempt at Story Writing)
It all started one day when I was invited to my best friend Dave’s house for a house warming party. He had just purchased the house after a harsh divorce and he wanted to break it in the right way. So, he invited a few friends who in turn invited friends.
It turned out to be a bigger party than what he was expecting. The more the merrier was all he could say. There were at least 60 people in all running throughout his house, in the back at the pool and it even spilled over into the front yard. It was not a rowdy party, so there were no police called. Thank goodness for that.
Anyway, Dave and I were like brothers, we grew up together and always watched each other’s back. As the day wore on, the party slowly started to break up; it was about 10 or 11 that night. There were around 10 people left and Dave made the suggestion that he take everyone out to the local bar. This was only due to the alcohol having run out. He said that he was buying.
Everyone was up for that, with the exception of Tyssa and me. We had a game of pool going and we really did not want to stop. So, I approached Dave and said that I would like to stay and finish our game of pool. Of course he had no problem with that and he tossed me the keys and said for me to meet him at the bar once we had finished.
Now, I am not what I consider to be a good looking man. I am 5’8” tall, slight belly but still fit. I have greying hair, mustache and beard. I am somewhat fit for my body type. I didn’t like to work out, but I tried to make up for that with daily walks and hikes.
I had met Tyssa while walking through the house introducing myself to people I did not know and saying “Hi” to those I did know. Tyssa was sitting outside on the patio. Tyssa was a beautiful lady. She stood about 5’9” tall, with long sandy blonde hair, pert double D breasts and very sexy legs. She was wearing a jean mini skirt, which showed off her legs very well. She had on a black lacy top in which one could see her breasts. She did not seem too embarrassed to have worn such a revealing top. She was also wearing black nylons and shoes to match her outfit.
I approached her and we introduced ourselves. I then asked her how things were going for her today. She said that she was just waiting for her turn to play a game of pool. We talked with each other until she was called to take her spot at the table. I followed her inside and I sat back and watched her play her game. They were playing winner keeps the table. Well, I decided to put my name in the pot for my turn at playing.
Tyssa was a very good player; she had beaten everyone who had come up against her. Finally it was my turn to play against her, the party had been breaking up slowly up until the time I finally got my chance to play. I approached the table and racked the balls. As the game got started, that was when Dave had called out for a party at the bar.
I looked over to Tyssa and asked, “Would you like to join us and go to the bar? It’s not very often Dave offers to buy.”
“No, I am not much of a crowd person. I guess I will just head on home,” she replied.
I didn’t want her to leave because she was the only one who wanted to carry on a conversation with me. “Would you rather just hang out here and play some pool?” I asked.
She looked over at me and asked, “What about your friend? This is his house, isn’t it?”
“Yes, it is but we are like brothers, he will not mind if we stay behind for a few games,” I replied. “Hey, Dave is it all right if Tyssa and I stay here and play a few games? She's not much into crowds and we are just getting started.”
He tossed me the keys and replied, “Sure. Here are the keys lock up and meet me at the bar when you're done.”
I turned back to Tyssa and smiled. “See, I told you he wouldn’t mind. Shall we begin? Let’s say best of five for starters.”
“You’re on!” she replied. She lined up for the breaking shot and the game was on.
I was really beginning to enjoy just being alone with her as we played. We talked as the games wore on. I ended up beating her 3 games to 1. I was starting to put away my cue when she asked, “What would you to say to 5 more games but we make it a little more interesting?”
“What do you have in mind as the stakes? How about 10 a game?” I asked.
“I was thinking something more along the lines of, if I win, you do what I tell you to do. If you win, I do what you tell me to do. Nothing is off limits. Sound interesting enough to you?” she finished off.
She definitely caught me off guard with that one. I stood there for a minute and thought about it. I was always told that if someone made a bet with you that it ended up being a sucker bet. I figured what the hell. I would be willing to do what she would want me to do, but I really had to make a stipulation. “I can go for that, but there has to be one rule to this. We do not make the other do anything that could get them hurt or thrown in jail.”
“I figured it would just pertain to the confounds of this room and nowhere else,” she said.
“Then you have yourself a deal. Best of 5 games and winner controls the other. I guess I will break, I was the winner of the last 5.”
I watched as her demeanor changed into a more serious player. I thought to myself that I was in for the games of my life, so to speak. I broke and started off real well. I had a run of the table going, which was up until she came up behind me and blew into my ear. I scratched.
“So, that is how the games will be played then, huh?” I asked as a sly grin crossed my face.
“Do your best, I think I can handle you and what you can dish out,” she said as she smiled back at me.
“Does anything go here as well? I mean, in short of hitting their cue or arm in order to make them miss,” I added.
“I’ll agree with that. Shall we begin the run of the gauntlet?”
It was her turn and I moved in behind her, but before I could do anything, she pulled back and poked me in the stomach with her cue. I laughed and told her that I wasn’t expecting that one and that she shouldn’t do it again.
She lined up for the next shot and I hurried over and grabbed her ass just as she was shooting. Her ass was so firm in my hand that I got an instant erection. I had never played a game of pool in this way before and it was really turning me on, especially knowing that anything goes while playing. Anyway, she didn’t miss. She was just as steady as if I hadn’t done a thing. I knew I was in for one hell of a game. She beat me badly, I never stood a chance.
We played the last of the games and as we did it turned more and more into a very touchy-feely game. She had grabbed my ass, played with my cock and balls (I know that she had felt the stiffness in my jeans when she had done that), kissed my neck and she had even exposed her breasts to me while shooting.
Needless to say, I had my ass handed to me in more ways than one. I laid my cue on the table and looked over to her. “Well, it was a sucker bet and I lost to you, fair and square. I am yours to command,” I said.
She just stood there and said nothing. I walked over to her and as I did she lowered her head. I asked her what was wrong.
“I don’t think I can go through with this, I have deceived you and I do not think it fair. If you truly knew the truth about me, I really doubt you would have made this bet with me,” she said.
“I don’t understand. We were both in agreement before these games ever began. I knew what I was getting into when I made the bet,” I stated.
“No, you really didn’t know what you were getting into. I am not like any girl you may have been with. I am different,” she commented.
“Now I am lost. You were so excited to play and now it comes down to claiming your winnings, you are backing down.”
She slowly began to unzip her skirt, but she would not look up at me. “Here, I will show you. I just hope that I do not get hurt once you see what I am talking about.”
After unzipping her skirt, she bent down to remove it. It wasn’t until she stood up that I noticed the bulge she was so desperately trying to hide. I just stood there in a state of shock, not knowing what to say but at the same time I was really getting turned on. I never thought of myself as being gay in any way, but seeing her in this way was making me rethink my life.
I walked over to her and I lifted her head up so that she was looking into my eyes. I didn’t know what came over me, but I leaned in and began to kiss her on her mouth. She was a little resistant but slowly relaxed and allowed my tongue to penetrate her mouth.
We kissed passionately and I slowly began to run my hands down her waist and back to her nice firm ass. I pulled her into me and I felt our cocks start to rub against each other through our clothing. I was harder than I could ever remember being in all my life. She hugged me and pulled me into her as we continued to kiss.
I stopped kissing her just long enough to lift her up and sit her up on the pool table. I started kissing her again and I let my hand roam between her legs until it brushed against her cock. I felt as it flinched from my touch, so I reached inside her nylons and set her cock free. It began to stiffen under my touch.
I stepped back and when I did she looked up at me. “Well, It looks like I know your secret and as I have just showed you, I do not have a problem with it. Again, I lost our bet and I am yours to command.”
“You really mean it, don’t you? Bill, forget I just asked that. I know you meant what you said,” she stated.
“Command me, Tyssa. I want to pay my debt and I want to pay it in full,” I said.
She looked at me and said, “Remove my clothing, help me to get undressed.”
I slowly removed her nylons and I made sure to rub her smooth, sexy legs as I did. I then stood up and helped her to remove her top. Once I had it over her head, I looked down and saw her big perky tits and I was just about to lean in and suck on them, but I stopped because I was hers to command. I would not make a move until she commanded me to do so. I stood there waiting for my orders to begin.
“Kiss my breasts; I saw how you were looking at them. I know you want to. Kiss them and then I want you to suck on each one, bite the nipples gently because they are very sensitive.”
I did as commanded and I began to suck each breast and bite each nipple as I did so. She began to moan with each suck and nibble I gave to her. She ran her fingers through my hair and pulled my mouth tight over her breast. “Suck it, Bill! Suck it harder!” she let out. Again, I did as commanded.
She released her grip from forcing my mouth on her breast and leaned back. “Have you ever sucked a cock before?” she asked.
“No, I never really thought I would be put in this position to do so. I never thought of myself being gay let alone bi,” I replied.
“Then, I will make this as enjoyable as I possibly can. You are my first virgin, so to speak. I want you to enjoy it and at the same time come back for more.” She jumped up off the table and stood before me. “Kneel down and take my cock into your mouth,” she commanded.
I slowly sank to the floor and I was staring at her cock as it twitched, coming to life. She pushed her hips forward towards my mouth. I reached up and grabbed her cock and…I couldn’t believe what I was about to do...I opened my mouth and I let her slide he tip in.
I could taste her pre-cum as it slid past my lips and onto my tongue. She tasted salty but sweet. Slowly she pushed her cock into my mouth until I started to gag a little. She was testing to see just how far she could get her cock down my throat. As I began to take more and more of her cock down my throat, I felt it grow some more. I tried to pull back but she grabbed my head and began to fuck my mouth. Slow and steady, with each thrust I found myself taking damn near the entire length of her 8.5” cock into me.
“Yessss, that’s it Bill! I will go slow and easy. You are sucking cock like a pro. When you think you are truly ready for the face-fucking of your life, just moan out loud and I will take that as a cue to really fuck you good,” she said.
I let her work her length into me until I did finally have it all in with very little gagging. I moaned out loud and I let her take it from there. She again grabbed my head and began to force feed me her cock. She was picking up her pace and I felt her balls slap my chin with each thrust. She would go slow and then pick up the pace again. This went on for what seemed like eternity.
While she pumped her cock into my mouth, I reached up and slid my hands to her ass. I spread her ass, found the entrance and did everything I could to slip a finger up her shitter. My finger found its mark and when she pulled back, my finger broke through her entrance and went in up to my second knuckle. I started working my finger in and out of her ass at the same tempo as she fucked my mouth.
She moaned out loud as she pushed back into my mouth and held it there. “I’m cumming, Bill!” That was when I felt the head of her cock expand, her balls tighten and a thick warm gush of cum blast the back of my throat. I swallowed what I could, but the pressure was just too much that it escaped through my nose and out the sides of my mouth. I swallowed as fast as I could, but it wasn’t enough. Tyssa was shooting tons of cum for me to swallow.
When she finished shooting her load, she slowly withdrew her softening cock from the back of my throat. She pulled me up to her and she began to lick her cum from my face and chin. “You are the best cock sucker I have ever had the chance to be with. I am not just saying it, but I really mean it.”
“Thank you, I was scared at first, but you did what you said you would do. You were gentle up to the point I said that I was ready,” I said. I grabbed her head and I began to kiss her again, only this time there was a lot more passion behind the kiss.
“Did you really like that? Would you ever think about doing something like this again?” she asked.
I looked at her and replied, “I would love to do this again, but only if it can be with you. I would also like to reverse the role from time to time and maybe someday have my virgin ass taken.”
“I would love to get together again. I have so much to teach you and I know that there are things you would love to do to me, but until then…”
With that she dropped to her knees and gave me the most intense blow job I have ever had. We went into the restroom and cleaned up. We exchanged numbers and she left. I locked up and headed to the bar to meet my friend and to give him back his keys. While en route, Tyssa called me and said for me to drop by when I left the bar. I wrote down her address and was so looking forward to getting there.
