tagTransgender & CrossdressersJenna & Stephen Ch. 02

Jenna & Stephen Ch. 02


AUTHOR'S NOTE: My intention all along was to follow up with the progress in our relationship shortly after my original story, but so much has happened since that the story I'd start to write would be scrapped again and again. Here is the latest. Thank you so much to those of you who gave it such a high score, for your comments and constructive feedback, and for your requests for more. My apologies for the delay. I hope this installment is to your liking. As with the first story, the following is absolutely true, with only the names and very minor specifics altered to protect our privacy.

A lot has happened between Jenna and I since that fateful afternoon when we shared our wildest past experiences, and then lived-out my kinky secret the very next day.

While there have been very different circumstances since then, our sexual relationship has still mostly revolved around my affinity for being pegged by a woman with a strapon. Jenna has become an expert at it and we have continued to enjoy this activity in various ways.

What we still had not done, until just recently, was to further explore Jenna's kinky desire: a threesome with a shemale.

We had talked about it, off and on for quite some time. Her only experience with a shemale, while very pleasing for her, was somewhat disappointing in that she wished her boyfriend-at-the-time had been more interactive with the shemale.

This was a tricky proposition for me, one that I was not ready for. I am a total slut for Jenna's strapon, but the real thing -- even in the form of a woman, as a shemale uniquely offers -- was a big emotional hurdle for me to overcome.

The topic came up more and more in conversation, to the point that it was now a matter of when, not if. We began watching shemale porn and it quickly went from my feeling squeamish, to being mildly curious, to eventually a full-on desire. Watching shemales pornstars such as Allanah Starr, Gia Darling, etc., I yearned to feel their cock.

The time had come for us to take the next step. We visited a website that lists local escort services. The site offers various categories, including Shemale Escorts. We checked out each, and both of us kept coming back to the same one in nearby Hamilton: Soda.

Soda's descriptions were very hot, but her photos were what really did it for us. She truly looked like a woman, one who would turn any male head in her direction. She was beautiful, busty, and claimed to have a fully functional 8 inches. We were sold.

Jenna called Soda later that night to set it up. The plan was for Soda to meet us at a nearby hotel for the upcoming Friday evening, a two-hour appointment.

The days leading up to it were torture, both because of the nerves, but also in the intense anticipation and desire growing within us.

While it felt like a long time, in reality Friday night quickly arrived. We checked into the room and sent a text message to Soda with the room number. My nerves, while still present, were diminished considerably by Jenna who was a cool as a cucumber. This was her fantasy about to come true, plus with her previous encounter with a shemale, she wasn't the least bit nervous.

Jenna looked gorgeous, dressed in her jeans, high white "stripper" heels and white bikini top. I was admiring her beauty when there was a knock on the door. We both jumped, me in startling realization of what was about to happen and Jenna is exuberant excitement. She practically ran to the door as I wondered if I could still back out of this.

As Jenna opened the door, any thoughts of leaving seemed absurd. I was taken back by Soda's beauty. She entered and we exchanged our pleasantries and Jenna handed Soda the envelope containing our "tribute" for her time.

Unbeknownst to me, when booking the appointment, Jenna mentioned to Soda that I was quite nervous. Soda told her that it's been her experience that most new guys need her to take charge. She suggested I might need that. Jenna agreed.

As we stood there and I wondered where we would take this next, Soda brought her hand around my head and her lips to mine, she locked me into a passionate kiss that had my cock instantly hard. Jenna stepped next to us and Soda released her kiss to me in order to kiss Jenna. Then Jenna kissed me, and it went like this for a few minutes.

"Both of you get undressed," Soda ordered. We both obliged, with Soda watching closely as if she were inspecting us to ensure we met some required standards. "Jenna, remove my dress," said Soda.

Jenna removed Soda's dress, as demanded. I could see an impressive bulge in Soda's panties. "Now Stephen, come and undo my bra," was Soda's command. I happily obliged. Her tits were perfect! Soda put her hands on my shoulders and pushed me down until I was on my knees, inches from her still hidden cock. "Take my panties down, but use your teeth," Soda instructed. I bit the top of her panties and pushed them down. As I went far enough for her cock to come out, her erection brushed my face.

"That's enough," Soda stated. With her panties hugging her thighs and her rigid cock staring me in the face, Soda looked into my eyes and though she didn't say a word, her silence spoke volumes. I knew what her next order was. I opened my mouth and engulfed her cock. Soda winked at Jenna, who approached for a better view.

I was slowly slurping on Soda's cock, the way I've done on Jenna's strapon so many times before this, but while my motions were the same, the feeling was very, very different. I loved sucking Jenna's rubber cock, but to have Soda's real cock in my mouth was intoxicating. It had already been hard before I wrapped my lips around it, but since then I felt it go even harder in my mouth. I hadn't yet touched my cock, but I was so excited by this that I could feel pre-cum soaking the tip of my dick.

Jenna crouch behind me and began jerking my cock with her right hand, while her left guided my head up and down on Soda's length.

Soda pushed my head away and Jenna leaned in for a kiss, as if she wanted to taste Soda on me. She then took her turn on Soda's cock as I stayed on my knees jerking off and watching this little show.

We then moved to the bed, where Jenna lay flat on her back. Soda moved in between her legs and rubbed the head of her cock on Jenna's hungry pussy lips. Soda's cock disappeared inside Jenna, who moaned aloud in response. Soda began fucking Jenna hard with legs pointed skyward.

When Jenna became rocked by her first orgasm, I moved over top of her in the 69 position. She took my cock back into her mouth and Soda pulled her cock out of Jenna's still-tingling pussy. I sucked Jenna's juices off of Soda's pole. Soda slid her cock back into Jenna again, as Jenna sucked my cock. Then Soda and I kissed. I wish we'd had a camera because I'm sure it would've been a beautiful sight: Jenna on her back with my cock in her mouth as I faced away from her; Soda ramming Jenna's pussy and leaning down to make out with me.

After Jenna came a second time, Soda pulled out and I once again cleaned off her cock. "Your turn," Soda said to me. I lay on my back as Jenna had done and likewise threw my legs up in the air, my ass eager to welcome Soda's prick.

Jenna, still trembling from her orgasms, managed to lube up my ass. Soda's cock kissed the edge of my asshole, before slowly, but wonderfully sliding in as far as she could. I moaned in ecstasy as she filled me up.

Soda expertly held her position as my ass hugged her cock. Like a train starting from a dead-stop, Soda rhythmically began fucking me, slowly at first, then harder and faster until I was screaming in pleasure.

This continued for a few minutes until Jenna was ready for more fun herself. Soda helped me up off the bed. Jenna lay down on her back once again. I climbed back up and slid my cock into Jenna's soaked pussy in the missionary position, but with my ass sticking out as much as I could manage, inviting Soda back in. Our newest friend did not disappoint. Her cock slid into my ass easily. We were a bit clumsy and awkward at first, Soda fucking my ass while I fucked Jenna's cunt, but we soon developed a steady rhythm.

"You like getting your ass fucked by her big cock, don't you?" Jenna panted. "I... I do... I love it," I stammered. Soda began whispering into my ear that she wanted me to cum. She picked up the pace of her ass-fucking and before long, my cock exploded inside of Jenna. I thought my heart would stop because it felt so intense cumming, all the while Soda never let up on my ass.

Soda told Jenna to scooch up on the bed, and then she drove my face into Jenna's creamy pussy. I gladly munched on her pussy, eating my delicious creampie. I ate up as much of my cum as I could before Soda's breathing became labored. She pulled my head away from Jenna, then pulled her cock out of my ass and quickly ripped off her condom.

In the meantime, knowing what was about to happen, Jenna and I both lay on our backs with our head below Soda's cock, Jenna's head next to mine. Soda gave her cock another few strokes before her cum erupted into mine and Jenna's open mouths. Soda spurted all over our faces and chests. When her delicious assault on us stopped, Jenna and I began kissing and licking Soda's cum off each other.

Soda lay next to us as we kissed, all three of us exhausted from our fun. A few minutes later Soda excused herself to the shower. She came out to find Jenna and I in the same spot she left us, still kissing deeply.

Soda slid her tongue in with ours, thanked us and told us to call her again soon, and then let herself out. Jenna and I remained in our embrace for another hour before we fell asleep in one another's arms.

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