tagTranssexuals & CrossdressersAmy Finally Lives Out Her Fantasies Ch. 02

Amy Finally Lives Out Her Fantasies Ch. 02


(Author's Note: This is a continuation of "Amy Finally Lives Out Her Fantasies -- Shy Amy uses her strapon on Kyle". Thanx to all who provided such great feedback. Hope you like part two. Warning: this story contains male/female strapon sex, cum eating, and as the category suggests, shemale sex. If those aren't your things, you won't enjoy this story. Love to hear everyone's feedback so please let me know what you all think.)


"Wow! What got into you?"

"I don't know, I just decided to finally loosen up and go with my desires," she explained. "Did you enjoy it?"

"Are you nuts? I LOVED every second of it!" I exclaimed.

Figuring the alcohol played a very large role in her sudden assertiveness, I decided to explore for more of her secret fantasies before her buzz wore off.

"Any other desires you want to let loose with?" I asked coyly.

"Well, yes, there is one," she said meekly. I feared she'd go back to her usual shy self, so I quickly asked what is was. She hesitated, and I felt I was losing the suddenly aggressive Amy. I kept asking, pestering really until she finally caved in and spoke up:

"It was just so hot watching you suck the strapon. Did you really enjoy it?" she asked.

"Yeah, I guess I did from the standpoint that you demanded it and seemed to enjoy it. I mean, it's just sucking a piece of rubber so it didn't do anything for me physically, but from a submissive, symbolic standpoint, yeah I liked it a lot," I replied, wondering where she was going with this.

"And obviously you enjoy the feeling of getting fucked up the ass, right?" she asked.

"Do I? It's such an intense, overwhelming feeling. What is it Amy, what is you want to say?"

In hindsight, perhaps I should've seen this coming, but the truth is I was caught completely off-guard by what she said next.

"My fantasy would be to see you suck a real cock and to take one in the ass too," she said.

I literally jumped off the bed. "What?" I yelled. "I might love a good assfucking with toys, but I am not gay. No way am I going to get it on with some dude!"

"I knew you'd say that," she told me. "But what I had in mind wasn't another guy."

Now I was completely baffled.

"I was thinking the best of both worlds," she began to explain. "A hot, gorgeous, sexy girl but who also has a cock... a shemale."

I had trouble separating a shemale from a man. "A guy in women's clothing? It's still a guy. Forget it!"

"No," Amy said. "I don't mean a crossdresser. I mean a shemale. There's a huge difference."

"What would that be?" I asked.

"A crossdresser, like you said, is a man who dresses and poses as a woman. A shemale is basically a woman with a penis. I won't get into all the psychological aspects of it, nor the surgeries and treatments to make them more feminine. Just imagine a smoking hot chick, but she has a cock. A threesome with two girls, me and another and we both have strapons... only hers is real."

I was so confused at that point, I didn't know how to respond.

"Just keep an open mind. I'll show you what I mean and if your answer is no, then we'll never discuss it again," she offered.

Amy got up to have a shower. I lay back on the bed reliving our discussion in my head. Where did such a hot night go so far off the tracks. I was regretting pushing Amy to express her desires.

Somehow, despite the fact my mind was racing, I drifted off to sleep.

The next morning I awoke alone. The only thing sharing a bed with me was a note from Amy that simply read "check your email".

I fired up my laptop and logged into my email and of course, an email from Amy awaited.

I opened it up and saw a number of waist-up photos of gorgeous women with big tits. Amy never sent me dirty pics before so I called her cell to find out what was up.

"Good morning love, how're you feeling?" she asked.

"Much better with naked women in my email," I laughed. "Come home, you've made me horny. I've got a massive hard-on needing attention."

"You like those girls do you?" She asked.

"Sure, what guy wouldn't?" I replied.

"Well..." she paused. "What if I told you those photos are of local escorts?"

"Uh, okay. So?"

"They're SHEMALE escorts."

"Get the fuck out of here, those ain't dudes," I said.

"That's right, they're not 'dudes', they're chicks with dicks, just think about it that way."

I didn't know what to think or say, so I just sat there staring at the pics on the computer screen, but did notice that my hard-on hadn't subsided at all. In fact, I felt a surge in my cock as I thought about these gorgeous women with a special surprise.

"Are you still hard?"


"I thought you might be. Why don't you take care of that. I have surprise for you tonight. We're going out," she informed me.

Later that night, Amy still hadn't told me where we were going except to say "for drinks". She was driving and I was pleasantly surprised when she pulled into the parking lot of a strip club I hadn't been to in years.

Amy and I had been to strip clubs before. I got out of the car and eagerly headed for the front door when she told me to stop.

"Were going to the back entrance," she told me. I hadn't known they even had a back entrance. I also had no idea there was a basement with a stage and bar, which the back entrance took us to.

We walked in and a stunning blond came to Amy to hug her.

"Kyle, this is my friend Ana." I could hardly breathe. This woman was a gorgeous blond with the biggest tits I'd ever seen. She wore a black fishnet dress over her bare chest and a black thong bikini bottom.

"Kyle is every bit as sexy as you described," Ana said in a sexy spanish accent.

"Ana is my friend from Miami," Amy told me. "She's a stripper in town featuring here this week. When are you on stage, Ana?" She asked.

"Not for a while, but why don't we go have a drink in one of the private booths," she suggested.

That sounded like a great idea so I happily followed them both past the stage where a brunette was dancing in a schoolgirl outfit. Ana led us to a secluded area of the club that had a love seat and a black curtain which Ana closed after telling a nearby waitress to bring a bottle of tequila and three shot glasses. The room was lit only by a small lamp with a cheesy red light bulb painting us in a red glow. When the waitress brought us the booze. Ana poured a round and the three us cheered each other before gulping back the shot of Cuervo.

"How long have you been a dancer?" I asked Ana. She surprised me by saying not very long, that she rarely dances at clubs, but she did some escorting and had a lucrative XXX website.

"One of my customers flew me here to see him. Since I was going to be in town, I hooked up with the club to feature for the week and I had to call Amy since it's been too long since we last saw each other."

As she explained, Amy poured the next round of tequila shots, which we gulped down. It was mainly small talk over the pumping bass of the techno music the club was playing.

A number of shots were consumed by us throughout the discussion when I felt something good was about to happen. I actually came to that conclusion because the few silences we had were clearly becoming somewhat awkward, especially between Ana and Amy. Something was up.

We sat there awhile and a slow, rhythmic R&B song came on. Ana stood up and took Amy's hands. They began grinding and my cock was twitching in sequence to their movements. I poured myself another shot, then sat back to enjoy the show the girls were putting on.

Ana pulled her fishnet outfit off and Amy quickly began to caress her friend's naked breasts. Ana looked at me and told me to take my cock and jerk it, which I was only too happy to do. As I undid my pants and my throbbing cock popped out, Ana pulled Amy's top off. Amy, who never wears a bra, helped her by removing her jeans and panties.

I stroked my cock slowly watching all of this as the two of them crouched down to my face. Amy slid her tongue into my mouth and our tongues wrestled as I felt a hand grab my cock and when I noticed Ana's fingers wrapped around my shaft, I moaned in ecstasy.

"Amy tells me you're her strapon bitch," Ana said. I was too drunk and too horny to be embarrassed so I smiled and said yes as her hand began to thrust up and down my length.

At that, Amy reached into her handbag and pulled out the strapon she used on me just the night before.

"Kyle has learned to suck my rubber cock Ana, and he's a natural at getting fucked up the ass," Amy told her. "Last night he even ate his own cum. He loved it, didn't you Kyle?"

"Absolutley," I said quietly, looking into Ana's eyes as her tongue flicked across the head of my cock.

"Mmmm, I'd like to see that," Ana said. By then Amy had already put on her harness and brought her rubber cock to my face. I looked down at Anna, who was still knelt on the floor between my legs. Ana opened her lips and took the head of my cock into her mouth, closed her eyes and I watched my entire length dissapear into her warm wet mouth. My eyes rolled to the back of my head and Amy pushed her dildo towards my lips. I opened my mouth and tried to suck her strapon the way Ana was doing to my cock, but was so distracted by Ana's incredible blow job that Amy was really just fucking my face more so than I was sucking her dildo.

Ana stopped her blowjob and Amy straddled me, sliding my cock into her tight pussy, her strapon dildo pressed against my stomach. Ana was behind her and I couldn't see what she was doing, but it turned out she was removing her bikini bottom.

"Did you like sucking my cock?" Amy asked. "Yes, I loved it!" I answered between moans as Amy rode me.

"See if you like Ana's too," she said and I saw that Anna was wearing a strapon of her own. I looked hungrily at the dildo between her legs when it hit me. There was no harness holding her 8" strapon. As Ana brought it closer to my face, I looked up at Ana, then to Amy. Ana was not wearing a strapon at all! Hers was the real thing.

"Go for it baby," Amy urged. "I know you want to." Amy was right, at the moment, I really did want to. I kept my eyes locked with hers as I brought my hand up and grabbed hold of Ana's rigid tool. I opened my mouth and guided Ana's cock to my mouth and sealed my lips around it.

"Yes, Kyle suck it, good boy," she said as our eyes remained focused on one anothers'.

My tongue slid under the head of her cock and I finally looked up at Ana who put her hand behind my head. She pushed my head along as I bobbed on it. I performed the same motion as I had with Amy's strapon the night before, but there was certainly a big difference between the two experiences. Instead of a cold rubber object, Ana's was warm and fleshy and had a much different taste which I realized must be her pre-cum leaking out.

Amy was enjopying every second of this experience and before long she was fucking me to her first orgasm of the night. When she came down for her orgasm, she climbed off and told me to get up. As I did, Ana sat at one end of the love seat. Amy pushed my head down to bend over. She pushed my face back to Ana's hot cock that shone in my saliva. I went back to my blowjob when the familiar feel of lube hitting my asshole caused me to moan alound again. Amy's strapon dildo poked at my tight asshole and with slow, gentle force, she slid the rubber cock past the opening.

I stopped my sucking but still had Ana's cock in my mouth as I felt the wonderful intrusion Amy's dildo made in my ass.

I slurped Ana's cock hungrily as Amy slowly slid her strapon all the way until her belly was pressed against my ass. She slowly pulled it back, then began a continual motion of thrusts, like a piston moving in and out of me.

I felt like such a slutboy in this position, a rubber cock in my ass and a shemale cock in my mouth. I don't know which was more shocking to me: that I was in this situation in the first place; or that I was enjoying it as much as I was.

Before long, I was approaching orgasm and told Amy of this. She had me stand up and jack off on her tits. As she lay on the loveseat waiting for my load, I stood above her fisting my cock. Ana was doing the same with hers and we locked our tongues in a passionate kiss. I felt the jolt as my cock exploded, leaving a sticky mess all over Amy's chest. I leaned down to lick my cum off of her, occasionally bringing some to her lips. Ana stood stroking her cock as I remained on my knees kissing Amy.

Ana's breathing grew into a number of fast, short breaths as she approached her own orgasm. She took my head and guided it back to her cock. I began sucking hard and fast like a seasoned pro as her moans increased. The feeling of her cock in my mouth as she released was unreal. Her cock twitched and a gush of her delicious cum washed into my mouth. I tried to swallow it all, but as this was my first experience, I couldn't and pulled my head away just in time for another orgasmic twitch shot another blast of cum on to my face.

Amy licked that load off my face and brought it back into my mouth. Ana brought her cock to our lips and both our tongues licked at the drips of cum still leaking out, before kneeling down and the three of us exchanged kisses.

Amy looked at me lovingly and asked how I'd enjoyed the experience. I gladly admitted that I'd loved it.

"So did I," Ana added. "But I didn't get a chance to fuck Kyle's ass, nor did I fuck you Amy. I have to get ready for my stage show, but once that's done, I hope we can continue this party."

"Well, that's up to Kyle," Amy added. "Think you're ready to get fucked by Ana?"

"Oh I'm ready, all right," I told them.

The three of us relaxed for a few minutes before getting dressed again. Then Ana left to prepare for her show. Amy and I moved from our booth to a table near the stage to watch her performance.

Knowing what was to come afterwards, I couldn't wait for her show to end.

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