I was too shy to tell Tracy my real feelings for her, so I was extremely surprised that my secret love interest decided to take matters into her own hands. We had a passionate lovemaking experience in her bathtub, which ended after I shot my love deep inside of her.
To add to the day, I proceeded to also have sex with her two other friends, Brooke and Suzy, while getting dressed and having make-up applied to me. When nine o’clock came, we left for the nightclub. I passed my first test when we were waved into the club. Eventually we met my friends, and after dancing it turned into a night of teasing and making out before Adam suggested we continue the party at his place. On the way there, Mark asked if I wanted to “experience what Mark can give you”.
My sudden and internally shocking reply was, “Yes, I do. I’ve been waiting for this moment for a long time…”
Mark escorted me into Adam’s living room and led me to one of four loveseat-style couches. The couch that Mark led us to was just to the left of the center of the fireplace. I was very familiar with the tales of this loveseat, and everything that Mark has done to women he has picked up. I have to admit that sitting on this couch in the situation I was in, really made me heat up inside. A part of me was fighting this heat as I really had no attraction to guys and didn’t want to go far with Mark other than some kissing and maybe me playing with his cock a little bit.
The other side of me was telling me to let go and let Mark have his way with me. It was a massive conflict of emotions and thoughts. When Tracy walked into the room with John, it only further made me a wreck of emotions. I wanted to be there, yet I really didn’t. I wanted to wrap my arms around Tracy while we made passionate love, yet I wanted Mark to wrap his arms around me as he had sex with me. The conflict, fear, and anticipation were showing in my eyes, and Tracy saw it.
Tracy stopped John for a second and said to me, “Sweetie, is everything alright?”
I shook my head no.
Tracy came over to me, grabbed her purse and my hand, and said to the guys, “Pardon us for a second. Where is the bathroom so we can talk in private?”
John sighed with the’ here we go again’ look, and pointed in the direction of the bathroom. Tracy led me inside and shut the door.
Tracy started it off. “Hun, what is wrong?”
“I am such a wreck of emotions right now. I want to do this, but I don’t. I want to make love to you and not have John ever touch you, yet I really want Mark to wrap his arms around me. I don’t understand what is going on. I’m a guy with no attraction to men, yet I really want to experience being a woman. On top of that, I am terrified that they will catch on once Mark and I get into it. I may accidentally give up my secret.”
Tracy replied, “I understand your emotions. A lot of women, including me, go through this at one time or another. It’s natural. For me to get out of the roller coaster of emotions, I just go with the flow of events and see where it goes. As for John and I, I have zero attraction to him. I am doing this for you, not for me.”
I nodded.
Tracy continued, “You are the only one that will take me bare from now on. You are the only one that I will wake up next to every morning after tonight. You are the one I love.”
“And I love you so much as well,” I replied.
Tracy looked at me. “So go on and see what happens. Enjoy tonight. If you really don’t want Mark to find out your secret, tell him it is your time of the month and that you’ll either suck him off or let him take your ass. Tell him it’s all clothes-on, panties moved to the side. If he doesn’t like the idea of not sticking it in a vagina, tell him it’s your time of the month, and that you don’t want it in there.”
My fear and conflict was slowly fading away.
Tracy finished with, “I forgot, we need this filmed.” Tracy took the small camcorder from her purse and handed it to me. “If you do get into it, ask Mark to film it. I want to have your first experience as a woman forever captured for us to enjoy.”
I took the camcorder from her hands, smiled, and gave her a soft and gentle girl to girl kiss. Then we walked back to the living room.
When Tracy and I got back into the living room, Brooke and Suzy were doing a slow and sexy dance in the middle of the couches. Each gyration of theirs was getting more and more sexy and suggestive. The guys were all on their prospective couch watching the action unfold. I walked over and sat next to Mark. He saw the camcorder in my hands, and gave a big smile.
“Is everything alright, gorgeous?” Mark asked.
“I was cramping up, but everything is alright now.” I stated.
With a smile, Mark leaned over to me and gave me a kiss. “It looks like you’ve come prepared. I’ve never had a girl willingly want to be recorded. This will be so hot.”
I blushed.
Suzy and Brooke continued their dancing. I noticed that several articles of clothing were missing and they were down to their sexy lingerie. They kept dancing, kissing each other, and touching each other in their most intimate of parts. The temperature of the room seemed to be getting hotter. It was obvious that the guys were enjoying the show. Adam discretely unzipped his pants, pulled his cock out, and started rubbing it as Suzy and Brooke really got into their dance and each other. Brian quickly followed suit.
Suzy made the first move for the night when she got down on her knees. With Brooke still gyrating her hips, Suzy pulled down Brooke’s thong panties to expose her womanhood. Brooke never missed a beat as she lifted one leg and then the other so Suzy could fully remove her panties. Suzy tossed the panties to Brian. Meanwhile, Brooke took the back of Suzy’s head in her hand, and started to gyrate her pussy into Suzy’s face.
All of us on the couches were mesmerized by the scene in front of us. I was about ready to give up my true identity just so I could join the action with Suzy and Brooke. Then I looked over at Mark. He had taken his cock out and was stroking it. A feeling flooded over me that had never been this strong. I knew, right then and there, that I was going to go through with this and letting Mark be my first. I replaced his hand with mine and started stroking him as we watched the show. Tracy looked my way and smiled.
As Suzy and Brooke continued their show, Mark grabbed the camcorder off of the arm of the couch and started filming them. I turned toward Tracy to see that John was making his moves on her. John had already removed her shirt and was working on her breasts. The pang of jealousy rose inside of me. I really wanted to be with Tracy right now, but I knew that after tonight she would be mine, and mine alone.
Suddenly, I started hearing moaning coming from where Suzy and Brooke were located. Brooke had slowed down her gyrations so Suzy had continuous access to Brooke’s pussy. I was obvious that Suzy was doing an outstanding job of pleasuring Brooke. Adam and Brian were at the edge of their couches rubbing themselves faster and faster. Brooke finally collapsed onto the floor as Suzy continued her assault on Brooke’s bare womanhood.
Neither Brian nor Adam could take it anymore. They both removed their clothing and joined Brooke and Suzy on the floor. The events were finally unfolding.
Mark and I were now passionately kissing each other, and I was getting more and more excited.
Mark looked so dejected by my statement. It wasn’t true, but I didn’t want him to know my secret until after tonight was all over. I whispered into his ear, “There are two other holes you know.” Mark smiled and pointed the camcorder in my direction.
I got off of the couch, got on my knees, and faced Mark. His nice hard cock was inches from my face. As I was caressing his manhood and looking up at his eyes, it felt like a thousand questions were going through my mind. Did I really want to go through with this? What if I get caught now? Are my friends going to ridicule me? Will Tracy really understand? Will Tracy and I really make it as a couple after this? What does this episode make me? What if I really liked this? Yet as I stroked Mark’s cock and saw a drop of pre-cum graced the tip, my mind went blank and I went into autopilot.
I looked up at him and slowly licked the tip of his cock to remove the drop of pre-cum. I licked my lips so I could have that sticky and slightly salty lip gloss cover my lips. I then proceeded to lick his shaft, and then slowly take the tip of his cock into my mouth.
I looked over at Tracy who was watching me service my first cock. She winked at me and smiled. She then turned her attention to John. As I continued to put more of Mark’s beautiful cock in my mouth, I looked up at him with big doe eyes. The camcorder was close to the action filming every move I made. But what struck me was the look on Mark’s face. It was one of complete pleasure. From that point on, I knew I was going to be a good cocksucker.
As I continued my oral assault on Mark’s six-and-a-half inch marvel, I took a quick glance at the other action around me. John was between my Tracy’s legs giving her one heck of a tongue thrashing. Tracy was very vocal about where John’s tongue was, and was begging him to tickle her clit with his tongue. Brooke, Suzy, Adam, and Brian were a tangled heap of naked bodies on the floor. Brooke was orally servicing Adam while being eaten by Suzy. Brian already had his cock sunk deep into Suzy’s pussy and was pumping away with a big smile on his face. Now I finally understood exactly what my male friends did with the women they brought home. It wasn’t to simply pair up with them like I had imagined, but to make it a free-for-all.
Mark interrupted my thoughts by tugging my hair. “Babe, I’m already on the edge of releasing my load, you are so good at this. I don’t want to lose my load yet.” His hands slipped under my skirt and onto my panty covered bottom. He squeezed my ass cheeks and continued, “If you’re not willing to do me in the traditional sense, it’s only fair that I can enter through the back door.”
Oh-so-crude Mark was with that statement! I certainly hope he doesn’t win women over with that statement too often.
I replied back, “What’s in it for me if I let you in?”
“One hell of a ride, babe. Let me get some lubricant to make it really enjoyable.” Mark responded.
Mark walked out of the room to retrieve what he wanted. I looked around the room; Brooke, Suzy, Adam, and Brian were still a heap of naked bodies, although Suzy was getting pounded by Adam, and Brooke was on the receiving end of Brian. My Tracy was on her back with her legs spread as John’s condom-covered cock started its descent into her depths. Tracy looked my way, moaning as John entered her. Watching that felt like a dagger stabbed into my heart. I had no time to dwell on my pain, because Mark had returned with the lubricant.
Mark sensually oiled my ass cheeks and the little bud. He gently slipped a finger in to get some of the lubricant inside of me. I jerked a little, as it was unexpected. It was odd, but once John’s finger was inside me, it really felt good. A second finger felt even better to me. Sadly, both fingers retreated and left me feeling empty.
“Jessie, babe. Come straddle me reverse cow-girl style. I was to be able to watch myself slide into your nice ass.”
I really started to question if I was ready to do this. After all, I am a totally straight male with no desire for other males. Oddly enough, being all dressed up in this hot sexy dress made me want that cock inside of me. I straddled his legs and slowly lowered my ass toward his cock. Mark lifted my skirt some so he could see and record his cock entering me. As Mark’s cock head touched the crack of my ass, I felt one of the most unique feelings in my life. It was the feeling that his cock belonged inside of me, a feeling of becoming a real woman tonight. A feeling that I would never go back to a strictly heterosexual life style, and that Tracy and I will share many cocks in our future. It was the best feeling that Jessie has ever had.
I guided Mark’s cock to my boy-pussy entrance as I lowered myself onto him. I made it a point to move my ass as full of purpose and sex appeal as I possibly could have. I could feel the tip of his cock stretch out my sphincter as I lowered myself down onto him. There was definite discomfort and some pain, but I also knew it would be replaced by pleasure.
I continued lowering myself onto him, and felt inch after amazing inch slide inside of me. The pain was going away, and I was starting to get into the penetration. Every time I lowered myself onto Mark’s shaft, I would gyrate my ass a little. Mark was moaning, and then came the words, “What a good and hot little slut you are. Now let me go for a ride on your sexy little ass.”
I continued to raise and then lower myself a little more on Mark’s magnificent cock. I was really getting into this. As I continued to rise and fall, grinding my boy pussy onto his cock, I noticed a slight warming sensation inside of me. Mark was using a warming lubricant. It felt totally divine. After five to ten minutes of grinding into him, he grabbed my hips and raised me slightly. While still under me, he started to piston in and out of me at a quicker and quicker pace. The camcorder was capturing all of our moves and sounds. It was looking like it would turn out to be one hell of a movie.
As Mark’s pace sped up, my boy pussy was becoming hotter. Soon I was moaning with delight. Mark’s pace continued to increase as I started yelling out, “Fuck me, baby. Fuck me real good with your cock.” Little did I realize, my show had put a stop to all of the action and all of them were staring at Mark and I.
“Oh, baby, your ass feels so good and tight around me. I’m not sure how much longer I can take it!”
I shouted, “Oh god, Mark! You feel so good in there! Keep fucking me! That’s it! Harder! Oh god, harder!”
“Oh Jessie, babe! I’m not going to last much longer!”
“Fuck Mark! Your cock feels so good in my boy pussy! I want you to cum inside me! I want to feel your cum enter me! Make me a girl!”
Oh shit! Did I just say boy pussy and make me a girl? Oh crap, my cover is going to be blown!
“Here I cum!”
With one final thrust, Mark’s buried his cock all the way inside me. His cock started spurting load after load after load inside of me. As that happened, I cried out. “Oh fuck! Shoot your load inside of me! I’m cumming!”
I didn’t even realize my cock was rock-hard and pointing, making a visible tent in my dress. I was so into what Mark was doing to me that my cock swelled and shot several times inside of my panties.
As we were coming off our orgasmic bliss, his cock slowly softening inside of me, he started kissing me and caressing my fake breasts. Mark paused long enough to say, “No girl has ever gotten me off so fast or with such intensity. You are one hot and sexy woman.”
When I finally came to my senses, Mark’s cock was ready to pop out of my boy pussy. I looked at everyone in the room, and not a single person was doing anything. All of them had stopped somewhere in the middle of their sexual romp and started watching Mark and I. When I finally got to Tracy, I saw her smile, blow me a kiss, and mouth, “I Love You.”
