There was only one person that knew my need, my ex-wife and she is sworn to secrecy. My girlfriend, Karen, would freak and probably throw me out if she found out. When I was married, at least years into it, our desires began to come out, even though they weren't acted upon. I wanted it once, I needed it just once. The want to feel and see what it was like to sleep with a transvestite started to overwhelm my every thought. Jerking off to videos was getting old, reading stories just didn't fulfill it.
Karen left for the weekend to see her sister in N. Carolina. Now was my opportunity. So I went online to find an old friend, one I had met on a kinky chat room when I lived with the Ex. We had gotten to know each other quite well, each others real name, what we wanted out of relationships and so on. Amy lived in the South Jersey, two hours from where I lived. I had sent her an email with my phone number and asked her to call when she could.
"Amy? It's Charlie," his nervous tone could easily be heard over the phone.
"Well hello stranger, how are you?"
"Not too shabby, can't complain. Mind if I ask you something?"
"Sure ask away, you know I'm an open book." Confidence was never as issue with Amy.
"I'd like to meet with you. To....," then came the hesitant, fearful chuckle whenever I couldn't come up with the words.
"Are you sure? You know I've wanted you for the longest time."
"Yeah, I'm ready. You only live once right?"
"Definitely Sweetie, you know that resort out in the woods I've told you about, the one with the pool in the room? The reservation will be under Amy. Meet me there at 4."
"Alright, thanks darling."
"Anytime handsome, I want you to fuck me good."
"I'll do my best. See you there."
After hanging up the phone, I packed a duffel bag with a change of clothes, and then headed out the door. During the entire ride up the highway, the hard-on that my fantasies provoked practically touched the steering wheel. The Coliseum Resort was an hour away. It had themed rooms, each with an 8' by 10' pool inside of it.
It was 3:30, so I checked in and asked for Amy.
"Room D-21," the receptionist said with a welcoming grin. "If you are in need of anything please do not hesitate to ask."
"Thank you." I smiled back and took the keycard.
Down one hallway then another until I reached D Wing, then at the end of the corridor was Room 21. Sliding the card down then up, the latch to the door unlocked. Once inside, I dropped my bag and looked around. Walking from the sitting area into the bedroom I could hear someone.
"You are punctual aren't you, handsome."
"Sorry, I expected traffic coming up here. I'm not one for being late."
"Good." she responded with an evil grin. The vixen was coming out in her.
As she approached all the fantasies I have had were coming to life. Amy was just a bit shorter than me. Blue eyes, red lips, black hair, Size-D breasts and graspable hips made me shiver, yet I couldn't to move. Walking around me slowly, she took in a breath of my cologne and kissed my neck. My reaction was to close my eyes and let out a soft breath, the bulge in her dress caressed my ass.
"You will remember this night for the rest of your life Charlie", she whispered into my ear.
"I know." I did my best to calm down by taking long full breaths.
From behind she slowly undid the buttons of my shirt and yanked it from my pants, leaving me bare-chested. Her teeth would occasionally dig into shoulder, followed with a lick by the tip of her tongue.
"I've wanted your cock since we first started role playing Charlie. I promise to be gentle."
"I can't make that promise, that's how bad I want it."
"You're a rough boy, hmmm?" Amy put a hard slap to my ass, so I reached behind to find her cock and get a good hold of it, she whimpered from my touch.
"Pool first?" she asked
"Yes I want to see you wet."
She came back around to the front and immediately took her jet black hair out of its ponytail. That alone would give me a hard on. Her green blouse that revealed just enough cleavage was taken off over her head so I could see a hunter green lace bra. A black knee high skirt was unfastened and let to fall to the floor at her feet. I let out a soft growl, as all that was left was a pair of matching panties. Following her lead, my pants were unzipped and kicked to the floor with my shoes and socks, but 'I' took my boxer briefs off.
"My favorite color," I said while staring.
"I remembered," winking at me while in a lustful pose.
Walking a few feet to her right and down a set of three stairs was the pool, enclosed in a glass room to keep the heat in. Stopping at the edge, she turned, smiled mischievously and then went down the ladder into the pool. The moment her feet touched the bottom Amy went under, her hair was even blacker and sexier once it was flat to her back.
"Don't make me wait", she beckoned.
Getting in slowly, I could feel her watch every one of my steps. Once I'm in the water I turn and her lips leap at mine for a long lustful kiss. Our arms scanned over each other's body, mine held tightly to her ass, ours cocks teasingly sliding against each other. One of my arms gripped her soaked locks and yanked on it hard to pull her head back, so my kisses could be put to her neck and shoulders.
"Fuck, I want you", I said.
"Oh I can see that?" one of her hands wrapped around my cock completely, toying with the head then moving along my shaft. Before I could let go of Amy's hair she slid down my chest and under the water. Her hair hid what I could see from above but I could certainly feel what she was doing. Those gorgeous red lips engulfed my cock to where I could feel my tip graze the back of her throat. My animal instincts took over; both my hands grab the back of her head and pull her head towards my stiff dick. Amy gagged on it since I could see the bubbles come up to the surface.
She came up for just a moment to say, "Give it to me bitch." Taking in enough air, she then went back down, this time her hands held my ass cheeks and spread them wide. A finger journeyed around my cheeks and poked my brown hole. That finger went one knuckle deep while I controlled Amy's head. When it got to the second knuckle, I yanked her up to give her some air, then dunked her back down to finish me off. That middle finger is now fucking my ass, as my balls are filling with cum.
"Oh no Sir, not yet", she came up and the finger released my ass, "Your turn".
Amy then took charge and pushed me under, my hands pull down her panties to release quite a massive hard on. It seemed about the same length and girth of mine but hairless. Amy was shaved from head to toe. My lips touched it, and then opened to take in just the head. My heart raced as I went for it, opening my mouth and throat to swallow it whole, my needs took over. Sucking her cock came natural all of a sudden. I didn't care for the stigma, just what made me happy and I was taking it, I became Bi at that moment. Letting me up, I put those lips right to hers, "That was amazing Amy."
"Good, I knew you were a keeper." She then turned around; the crack of her ass was put in perfect position for my still raging hard-on.
"Are you ready to fuck me, Charlie?"
First, I reach behind for the waterproof lube and coat my cock; the other hand went between Amy's shoulder blades to push her forward and back under the water. My tip was lined up and slid in gradually to allow both of us to adjust, her ample hips allowed me to get leverage and pull Amy towards me. Her asshole overwhelmed the cock that went into it. Every five or six thrusts, Amy would come up for air, and then go deeper in the water, changing the angle and the depth at which my hard-on could go.
"Fill it, fill it Charlie, load up my ass with it."
My thrusts became furious, with a few more deep penetrations my load came out of my balls, through my dick and into her ass. "FUCK!!"
A few seconds later she swims away to the opposite edge to come up and smiles directly at me.
"That was nice. Now come to me," a finger summoned me.
Gingerly I went to her, because I knew what was coming. She reached under for my legs and put them over her shoulders, I was now floating, open and willing to be fucked. She used that same lube and pushed down by my hips, putting me underwater in the process. Amy's thick wood penetrated me with ease; but a scream still went to the surface. She would not wait, plunging her cock into my asshole feverishly. Ten or twelve pumps and she exploded into me. My legs came down to the pool floor after I caught my breath. Amy kissed me slowly and I returned it just the same.
"I want you again Amy. Karen won't be home until Sunday. I am here for the night"
"Then I am glad I brought my bag of toys, hmm?"