Jessica the Transsexual
I have worked for an advertising agency for a few years now, and recently I took a Managing Editor position in the agency. This was a huge opportunity with all the perks, money etc., that a person could want.
One day when we were having our morning meeting a new girl walked in who was gorgeous. She was about 5’7, exotic, and come to find out she was from Puerto Rico. When she spoke, she had a very sexy accent that was an even bigger turn on.
After the meeting, and I went back to my office I found myself thinking about the exotic Jessica. I knew she was an employee, and office dating is frowned upon so I knew not to pursue it.
Weeks went by, and I stopped thinking about Jessica until one Friday afternoon that I had a meeting with a few people in the department. Jessica walked into the meeting wearing a pencil skirt, high heels and a button down top that was tight and you could tell she had big tits.
She sat down at the table near me and she kept staring me down like I was prey. After the meeting she lingered after everyone left, stared at me for a minute, smiled and then left.
I looked at the table and saw a piece of paper with the name of a club, and the time 9:00 pm. I was so horny for the rest of the day, but had to contain myself. I got to the club at 9:00. As I got to the door I turned around and I saw her slowly walking up in a black dress, strappy high heels and she looked gorgeous!
“You look handsome boss.” I was about to reply, “Shh... I like calling you boss,” as she gave me a kiss, took my hand and we walked inside. After a few drinks and some idle conversation, “let’s dance, boss.” She took my hand and led me to the dance floor.
As we danced she made sure to either press her chest against me and kiss me or turn around and press her voluptuous ass against me and rub against my crotch.
After awhile, she whispered in my ear, “Let’s go to your place boss.” We then left and I followed her back to her place. I knew this was wrong, but she was so damn sexy, I had to have her.
When we got to my place she lead me to the living room where she sat me down, then sat on my lap and starting kissing me. She started kissing my neck, and then started undoing my belt and pants. She then pulled my pants and underwear down and started stroking my already hard cock. “I am glad that I can turn you on boss.”
As she was stroking my cock, she began to lick and suck on my balls, “Want me to suck you off boss?” I looked down at her as her tongue began circling the tip of my cock and nodded.
She then engulfed my cock as I could feel the back of her throat. “Oh shit that feels good!” She began to massage my balls as she was going up and down on my cock with veracity, “I want you to shoot your sweet cum down my throat boss.” She then went back to sucking my cock like a calf sucking for milk.
After a few minutes of intensity, “Oh God I am about to cum!” Right at that moment she stuck her finger in my ass! Despite the shock I could not believe how intense it made my orgasm as I exploded and shook as she massaged my prostate intensifying my orgasm.
Once I finished one of the best blow jobs I can recall, she kissed me, stood up and said, “Have a good night, boss. I will see you on Monday, smiled, and left the room.”
We would hang out on occasion, and she would give me a blow job then leave. I was wanting more, but if that was what she was into then I decided to go along with it. One night while laying on the bed and making out, she said she wanted to fuck, and in my mind all I thought was, “finally!” She got in the reverse cowgirl position on top of my cock and helped guide my cock into her ass! Not quite what I was expecting, but her ass was so amazing and felt so good on my cock I went along with it.
She rode me, moaned and she went back and forth on my cock. After awhile she her moans got louder and from what I could tell must have been fingering herself as she kept saying, “Come with me boss!” Watching her move back and forth was so arousing, and listening to her I eventually exploded as she began to gyrate and cum.
After a few moments, and I was planning to ask her why she wanted me to fuck her ass, she got up, got dressed, kissed me, “Thank you boss, you were amazing.” She then left.
Monday came and she acted like nothing happened, in fact a few weeks she hardly spoke to me, so I left it as a night of fun, and to move on. Then, the on Friday, as I was about to leave there was a note on my desk, and I could tell it was her handwriting.
“My place, 9:00 pm. Time to return the favor, see you then.” Signed, boss. Well, my mind was racing at the fact that I was going to hook up with her again, and I really wanted to get fuck her. Why did she sign boss? Oh well, she seems to know how to turn me on so I will roll with it.
That night I arrived at her place, and soon after I rang her doorbell, “The door opened, but it was kind of dark so I could not really see her. “Come in, and why don’t you have a seat” Well, it was different, but I figured I would roll with it again.
As I sat down in the chair I noticed the room was only lit by candles, so I could only figure she was in quite the mood to get right down to business. She came up from behind, handed me a drink then kissed my cheek, “I will be right back.”
After a few minutes of waiting and wondering what was going on she slowly walked in, then stood there looking at me.
She was wearing thigh high leather boots that had to be like six inches high! She had a leather bra top and a skirt, and she looked hot! “Tonight you are going to get me horny, then I am going to fuck you and show you who is boss!”
She walked up to me and we started kissing. I started kissing her neck, then undid her bra to unveil her beautiful breasts, and I could tell she got a boob job, but damn if they were not amazing to touch and kiss. I nibbled on her nipples and was kissing her stomach, “Ok, time to make your boss really horny, you have done good so far.” She pushed my head down, and I pulled up her skirt, and she had a penis!
“What the?” “I am a transsexual, and I got you off, now you are going to get me hard, and then I am going to fuck you.”
Before I could say anything, “If you don’t I will tell everyone at work what happened, and that you hooked up with a transsexual, so the way I see it, make me happy, or else.”
Well, I had no choice, so I grabbed her penis, which was quite large and started to stroke it, figuring this would be okay for her. After a minute of stroking and her cock was getting bigger, she then said, “Not bad, but now it is time to get to work, now open your mouth for your boss!”
I opened my mouth and she grabbed the back of my head and guided her growing cock into my mouth, then slowly put it into the back of my mouth. “Oh yeah baby, let’s get my cock wet, because I can’t wait to fuck you.
She was slowly face fucking my mouth, and I would gag on occasion. “Spit on it!” She took her cock out then I spit on it and she slid it back in my mouth as she kept sliding in and out, “Mmm..baby, you are making me happy and horny. Now take off your pants, and bend over for your boss.”
I did as she instructed, and then she walked up behind me and began to finger my ass. After a few moments I could feel the head of her cock begin to press against my ass. “You have such a nice tight ass, I am going to enjoy fucking you.”
It definitely was hurting as she began to push the head of her cock inside my ass, “Uh..ugh..shit!” “Aww, is it hurting? I have only gotten started.” She pushed her cock in deeper as I could feel it fill me up and my ass squeezing her cock. She slowly pulled back, then a bit deeper, and at least she was being gentle as she was fucking my ass. “Mmm..your ass really does feel nice around my cock, I am honored to be the one to take away your virginity.”
Her pace quickened a bit, “Oh shit, damn, it still hurts,” As she began to dive deeper inside and giggled at me. She reached forward and began to stroke my cock a little, “Mmm..can’t help, but notice you are already hard for your new boss. If I didn’t know any better I would think you are starting to enjoy getting fucked by your boss.”
That is when I realized I was hard, and I was starting to enjoy this. Is this right? Do I like getting fucked in the ass? “Uh..fuck..oh..shit yeah!” As she began to fucking me harder I was beginning to enjoy her cock sliding in my ass, and was turned on by her taking over my body and using me. “Mmm..your boss is happy, and now I am going to fuck you like the servant you are!”
She grabbed my hips and began to fuck me deeper and faster, as my ass was now hers to do with as she wanted. “Oh God yesss..that is it, fuck me boss, fuck my ass like the slut I am ..Oh God yes!” A few moments of fucking my ass ferociously, ”Your boss is going to cum you slut!” At the sound of her saying that my cock began to explode with cum all over as she began to thrust harder a few more times until she gave one last thrust deep in my ass.
I could barely hold myself up as she then pulled out of my now aching ass, but yet it was satisfied with what happened. “Mmm..your boss is getting very happy with you, and now you can let yourself out. Have a good night slut.”
She left the room, and as I laid there confused, I got dressed and left. I was not sure what to think about all of it, but I figured she got what she wanted and I was off the hook. I was surprised out how much I did enjoy it.
The next few weeks went on like nothing happened and I figured she was done, and got what she wanted out of me. Again on a Friday, I was sitting in my office and she walked in, closed the door and locked it. She walked up to me, and sat on the edge of my desk and kissed me passionately and with a fire that was erotic.
“Mmm..I am glad you enjoyed your time with your new boss slut, but I have one more thing to do with you before I am happy with you. Meet me at my place tonight at 8, and don’t be late for your boss.” She kissed me again and rubbed my crotch, then left my office.
I was not sure what to think, but I knew I was turned on, and now wanted more of her, even if she was different, but still very sexy.
I knocked on her door, and when she opened it, she was wearing some sort of trench coat smiling. I was not sure what to think, but I knew she was up to something. I walked in and she led me to the bedroom. I realized this was going to be interesting already. She sat me on the bed, kissed me then walked out.
A few moments later, she walked back in with another girl wearing a trench coat. They came up to me and both kissed me, took a step back then took their coats off. Both of them were wearing lacy bras, garters, thigh high stockings and high heels. “This is my friend Vanity. I told her about you, and now she wants to fuck you.” Vanity was about the same height as Jessica, auburn hair and had huge tits. She walked up me to, gave me a kiss. ”I want you to pull my panties down so you can see what I have for you.”
I did as instructed as I slowly pulled her panties down to unveil a really big cock! “Lover, my cock is 10 inches, and by the time I am done, you are going to take all of it as I fuck you.” She kissed me again.
“Now I know you sucked her cock, and you are going to suck my cock too before I fuck you,” She smiled as I knelt down understanding my new role. I put her cock in my hand, started to stroke then kissed and tongued the head of her already thick cock. “Mmm, very nice, now put the head of my cock in your little whore mouth.”
I slowly put the head in my mouth as she instructed and circled it with my tongue. I could already feel it starting to grow in my mouth. She gently grabbed the back of my head and began caressing it. She then slowly slid her cock in my mouth deeper, then back out. “Good lover, you are getting good at begin my cock sucker. Now spit on my cock.” She pulled her cock out, and I spit on it, then she slid it back in my mouth, deeper this time, and made me gag a little. She pulled out, kneeled down and kissed me as our tongues danced together, which she was an incredible kisser. She then stroked my cock for a few moments. “You are making me very happy lover.”
She then stood up again, and there I was facing her huge cock again, “Proceed lover. My cock needs more attention.” I stroked her cock as I began to lick up and down her big shaft, then putting her cock in my mouth trying to go deeper in my mouth because I knew that would make her happy. I really wanted to make her happy.
As I began to take in more of her big cock I noticed Jessica walk around behind me. She pulled my pants down and began rubbing my ass. Veronica grabbed the back of my head and gently pulled me into her cock occasionally making me gag as she began to face fuck my mouth.
Jessica slipped a finger in my ass, and I noticed my cock got hard, and as she moved it around my prostate I was really getting turned on.
“Okay lover, suck her good because I am going to loosen your ass up for her big cock, and you are going to take it all.” She slapped my ass and began to push her cock slowly in my ass.
I moaned in pleasure as I was being violated by both of them and somehow it felt like a dream. After a few moments of easy her cock inside me Jessica began to start fucking me deep and hard as she put her hand on my ass occasionally slapping it. Veronica began to face fuck my mouth as I kept trying to keep up sucking her cock and making her happy.
So there I was on all fours, sucking the biggest cock I have ever seen and getting fucked like a dog, and in all of this, I loved it! My moans got louder as Jessica would fuck my ass harder and deeper. This was an amazing experience I didn’t want to end.
“I am going to cum lover!” Said Jessica, and she began to fuck my ass deeper and faster, then a few moments later, “Uuhh, yes baby that’s it mmm…!” As she came she thrust inside me a few more times until she leaned against me, bit my ear, “Mm.. very nice lover, I know Veronica is ready for you.”
Veronica grabbed my chin and pulled my face up and looked at me, “Mmm..now it is my turn.” She leaned down and gave me a kiss.
Jessica slowly pulled out of my ass and I saw her walk in front of me as Veronica now was behind me. Jessica’s cock was still hard and had cum all over it. “I came so hard inside you lover, and lubricated your ass for her big cock.
I felt Veronica’s finger slide in my ass slowly, as I knew Veronica was prepping my ass for what was about to be a brutal fuck, but somehow I knew I wanted this, and needed this.
She then started pushing her thick cock slowly into my ass, and even though it hurt, I was so turned on that it felt good too. “That’s it lover, give into your new boss..because your ass is about to be mine” she chuckled, which I knew this would be rough.
She pushed her cock in deeper, “Oh my God!” it was really starting to stretch my ass out! “You like that?” I nodded yes Maam.”, but felt so good! I love hearing you moan for me. I want you to moan for your boss when I really fuck you..mmm.” She slowly pulled back and then pushed even deeper. “Mmm..your ass is stretching out for me so nicely lover, you know you want to be fucked like a slut, and that is what I am going to do,” she pulled back again and then went even deeper inside, and now I wanted all of it.
“Don’t worry lover, I have a few more inches to go until all of my cock is ready to fuck you properly.” She pulled back again, but started slowly fucking my ass and going deeper with each thrust. Jessica was sitting in the chair watching me get fucked stroking her cock. “Give me that cock!” I moaned.
Seeing Jessica turned on like she was and getting fucked by the sexy Veronika was turning me on, and they knew it. “Look Jess, our slut has a big hard on, you were right, he really is an ass slut!” She grabbed onto my hips and start pumping my ass with vigor. “Oh god that feeeels good…oh yes!” I exclaimed, giving into the moment and wanting this more and more.
“Oh God, that’s it, fuck me faster!” She start pumping faster, and every stroke was amazing with her big thick cock just pounding me. “Uh, uh, yeaaah, oh god.” She slapped my ass. “Oh yeah, that’s it!” You are now mine!” She laughed and slapped my ass again.
She was pumping me at a rhythm now and I knew eventually I would cum so hard. “Ah yeah, feels so good Maam, God yeah.” “You like that baby?” I nodded in reply, “Oh God yes Maam, like that!” She slapped my ass a few more times. “Oh my God faster please!”
Her pace quickened, and felt so amazing. “Oh my God, I want to cum!” She slapped my ass again and chuckled, “Say please slut!” Then thrust inside me deep and hard. “Oh God, please please please make me cum! I will do anything, please!” She slapped my ass a few more times. “ You want to cum? Tell me you are now my pet.” I nodded, “I am now your pet Maam, God please make me cum!”
Her pace then quickened as she was now impaling my ass, and I knew I could not take this feeling much longer. “Oh my God yes yes, I am cumming!” My dick at that moment exploded with cum all over and the sensation was incredible. My body shook, and it felt like I was not going to stop cumming, and all the while she kept pumping me, which made this even more incredible.
Right as my body was starting to calm down, “Im cumming lover, yes, watching you cum was such a turn on!” She thrust inside a few more times, which felt amazing and my body was practically limp, but I was overwhelmed with this incredible feeling, until finally she collapsed on top of my back.
“That was great lover, you took my whole cock like a champ. Now go shower up and get into bed. We are going to take turns fucking you tonight.” I nodded, and did as they instructed, knowing my life would never be the same, if anything it was even better.
