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Becoming Jessica Pt. 05


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"Thanks. I feel sexy and comfy in this. I like your new set too." I replied as I placed the candle on a dresser and helped myself to a glass of wine and some ice cream.

Emma and I jumped onto the bed and laughed as we sort of danced on our knees to Rihanna's 'Cockiness' while sipping wine and eating ice cream. Careful not spill anything we placed our glasses on the night stand and continued to romp around the bed.

When the song changed to "Unfaithful" we both fell in a stoop next to each other and stared into each other's eyes.

"So, Jess" Emma said coyly and added "Are you tired?"

I knew the look in Emma's eye and tone in her voice. She was horny. It was a strange, exciting, and erotic feeling. My wife was looking at me not as her husband, but as her girlfriend. I was very aroused as well. My cock was stiffening in my tuck.

"Oh I see. Kind of sexy Jess. Hot" Emma giggled as she saw me untuck my hardening cock.

"Hmm, umm, now Emma." I moaned as I started to stroke my cock. I added in my soft voice "Tonight was so fun and erotic. Flirting, meeting guys. Shopping. Oh fuck. I felt so wanted. So alive."

Emma scooted closer to me, softly kissed my lips, and said "Yup, me too. Hot guys make me so wet. So do cute girls sometimes."

The feeling of our feminine, painted lips touching was utterly fantastic. Emma's hands began to explore my cleavage and then my backside. Her hands perused through and under my lacy PJ's. I responded by pressing my hard dick against the crotch of her PJ bottoms while kissing her neck.

"Oh fuck, Jess, I want you; oh my." Emma said with a pant.

"Hmmm, I know, I'm so fucking horny. I want a cock or something." I replied passionately.

Emma and I continued to embrace, kiss, and rub our smooth and feminine bodies. It was so electric and erotic. I wanted to fuck her as well as get fucked.

Emma broke from our embrace and said "Wait here, I got something, I think you'll like it."

Emma stomped into her closet and returned with a large box stamped with her college sorority lettering. Emma began to rummage through the box as I stroked my cock.

"Here it is." Emma said excitedly as she pulled out a dildo thing with all kinds of straps attached to it. She added [giggling] "I had some fun in college with this thing."

Emma removed her PJ bottoms and attached the gizmo around her waist. It was a strap on dildo. My jaw almost dropped. I never knew Emma was into such kink.

"So you wanted a cock eh Jess." Emma said with a big smile.

After Emma tightened the belt and straps she crawled back onto the bed and kneeled before me. The strap on cock was facing directly act me as I laid on my belly. I inched forward to it and began to lick the head and wetten it. As my saliva began to drip down the shaft I stroked it with both my hands and took the cock into my mouth.

The strap on cock was about 6 inches and resembled your average guy. I sucked and stroked up and down on the cock as if it was real and added the moans and 'hmms'.

"Ohhh, ummmm, that's it baby. Take it" Emma said in a rather contrived masculine voice.

"Ohh, yes, I love your cock in my mouth; but I really want this thing in my ass." I pantered.

I turned over on back and slid my PJ and thong bottoms to the side to reveal my asshole. I spread my legs and again started to stroke my penis which was still exposed.

Emma crept up to my anus and began to rim and lick it. She spit saliva on my cock which began to drip down my shaft and settle on my asshole. She stuck her tongue and a few fingers inside my ass to help guide some of her saliva into my opening while she took over stroking my dick.

Emma grabbed lube from the bedside table and squirted some on the strap on. She added "Oh I think you're ready for this cock."

"Yes. Fuck me." I panted as I began to lift up my legs and expose more of my asshole.

In a missionary style Emma pressed the head of her strapon cock against the opening of my anus. I had played with smaller dildos in my ass at my own pace, so it was a little strange and discomforting.

"Oh, slow, please." I whispered to Emma as the head of the cock pried open my anus.

"Just let me know when I'm in you." Emma passionately replied.

"Uhh, ohh, mmm. That's it. Ohh. That's good. Hmm" I moaned as I the felt the head of Emma's cock pop into me. I added "Oh fuck, you're in me. Fuck me, umm slowly. Oh fuck, ummm."

Emma picked up the pace as my ass started to loosen. She seemed to like taken on this masculine role .

"Yeah baby. Take it. Oh fuck. You're so fucking tight. Love it. So hot." Emma said.

As Emma continued to pound my ass I said in the most sexy way "Flip me over baby, I love it doggystyle."

I always fantasized getting fucked from behind by a hot guy. I found it extremely feminine, a little dirty, and really sexy.

Emma guided my body on my knees as I assumed the position with my puckering asshole well exposed. Emma glided her strap on cock back inside my ass and grabbed my hips.

"Yes, fuck me; ummm I love it." I cried out.

"Ohh you like it this way, don't you bitch." Emma said as she fucked me from behind.

I loved the dirty talk during sex. Almost nothing was off limits. I often imagined being with a guy who treated me like a princess out of the bed and a slut in the bed.

"Yes. Yes. Fuck me harder." I continued to cry out.

My dick was still rock hard. I began to stroke it with my right hand as my left arm propped up my body as I arched my back in the doggystyle position.

Emma continued to fuck my ass as I masturbated. I had cummed before with a dildo in me, but the sensations I was feeling were unbelievable. Emma's cock was hitting nerves and spots I had never felt before. The dirty talk sent me over the edge of ecstasy.

"Ohh, that's it baby, don't stop, oh; oh Fuck, oh my God" I yelled out as I jerked my cock and experienced the most powerful orgasm I had ever felt. I shot my cum all over the bedsheets and off the bed onto the carpet.

"Wow, you're a dirty girl Jessica." Emma said laughing.

Still panting I replied "Oh, that was so fucking good. Oh, my; loved it."

We cleaned up a bit and grabbed our wine and melting ice cream. As we finished our wine we playfully intertwined our legs together and kissed. Within a few minutes I could tell Emma wanted to get fucked as well.

"Hmmm. Soo. Ever used one of these Jess?" Emma asked as she coyly pointed to the strapon.

"Of course not. But I can learn." I replied.

Emma removed the strap on cock and adjusted the straps. I was already beginning to get aroused when Emma strapped the fake cock around my waist and above my still limp real cock.

It was a weird, yet passionate feeling. I still had my girly PJ's on, cleavage shaped breasts, makeup, and done up hair. Yet I was fitted with a fake cock to fuck my wife Emma. Even though my cock was still limp, it felt thrilling to be in this girly lesbian role.

With Emma on her back, I softly licked and stimulated Emma's pussy with my mouth and manicured nails.

"I'm so fucking wet. Fuck me" Emma panted as I got into position to prepare her pussy for my strap on cock.

I threw Emma's legs over my shoulders as I gently inserted my fake cock into her pussy. Emma was really wet and ready. The cock slid in easily.

"Oh yes. That's it." As Emma pulled my body closer to let me know she wanted more.

Emma wasn't super vocal during sex. She was more hands on. Guiding me when we had sex. After a few minutes fucking her I think she felt my real cock stiffen.

Emma said "Hey there. What's that. Ohhh. Ummm. Fucking double stuff me. Now."

I had fucked Emma in the ass before, but only on my birthday or other special occasions. She liked it, but said she didn't want it to be a regular thing.

I replied "Yes, so sexy, 2 cocks in you, oh my, so fucking sexy. You need that girl."

I briefly stopped fucking Emma so I could get my cock ready for Emma's ass. I quickly licked and spread her pussy juices over her butthole and stroked my cock which was still glistening from a mixture of my cum and lube.

"Oh yes." Emma quivered.

The strap on cock was a bit longer than my cock so I placed it into Emma's pussy first before placing the head of my cock into her ass. I was now in control with Emma's legs swung back over my shoulders as I entered both of her holes.

"Fuck! Oh fuck, yes, oh, fucking yes; give it to me." Emma screamed as I double fucked her pussy and ass at the same time.

I started to pick up the pace and depth of my thrusts after feeling Emma pulling me into her. I was close to cumming again.

"Oh, oh, don't stop." Emma shouted as she aggressively wrapped and squeezed her arms and legs around me pulling me even deeper into both of her caverns.

"Ohhhhhhhhh, Uhhh, Fuck, Yes; Yessss!" Emma cried as she convulsed and had a orgasm.

Almost simultaneously I whimpered "Ummm. So good" as a I cummed inside Emma's ass.

We slinked over in each other's embrace and panted for a minutes. I thought in my head this was the best sex we ever had together. But I dare not share that with Emma.

"That was the best you ever fucked me Derek, errr I mean Jessica." Emma jubilantly laughed.

"Oh whatever." I replied as I poked Emma in the ribs.

"Well that was fun. I got to clean up. I'm exhausted. Good night Jess." Emma said as she got up and gave me a wink. She added "Oh let me get that off you." as she removed the strap on cock.

I gave Emma a hug and scampered back to my bedroom to clean up. Whew! I thought to myself. Some 2 days. I loved being Jessica. I knew this was still the beginning. I had GRS appointments, dates with cute guys, and more girls night outs. I was nervously excited.

I removed my push up bra and thong to give my chest and boy parts a break and settled down into my girly bed for the night.

to be continued ...

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Post as:
 Anonymous6 months ago
Loved it!

Great story; can’t wait for part six.


 Anonymousover 1 year ago
Lucky boi

Wow so hot and sexy I wanna be Jessica!it would be a dream come true!since I was 12 I’ve dreamt of being my sister and here me think we got mixed up in the womb!i wish I was a sexy girl twin instead of the boy it would be so much fun and god what great things life would have been

zazrix9zazrix9over 2 years ago
As a Bi

guy this is a great series, specially when it reaches it's dual climax. I luv to suck cock, be fucked, and have my nipples twisted, butt be in the arms of a sensual woman.

zazrix9zazrix9over 2 years ago

scene, maybe they'll stay together.

 Anonymousalmost 4 years ago

I so loved this story being a pre op trans girl my self ...I just hope you add more chapters soon , as I want to read more about Jess and Emma's adventures .

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