Chapter 2: A Night to Remember

Still fifteen months earlier - Cleveland

“Hi! I’m Callie. You must be Mr. Mystery. Can I sit down?”

I simply nodded. I was glad my mouth had not fallen open. Just then, two drinks were delivered to our booth. They were doubles and looked to be full of bourbon.

“I’ve ordered us a round of ice breakers. I hope you don’t mind?”

Again, I simply shook my head. She then calmed me down by asking me simple questions about what I liked best about women. I found that my descriptions somehow seemed to always sway to her current appearance. She noticed my inclinations and gave me a wicked smile at my responses. My drink was smooth and was going down well. Soon we had both finished.

“We could stay here and get drunk but that sounds rather dull. Do you mind if we go to your room instead?” she asked.

This time I was able to get my voice to work and said smoothly, “That sounds like a great idea.”

When we were riding the elevator up to my floor the reality of the situation hit me with full force. With a clearly nervous expression I looked to her, “Uh ... Callie ... I hate to ask but...”

She smiled and put a finger on my lips. “Relax Hun. Yes, I am a professional. Yes, I’m all yours for tonight. Everything has been covered. I also have plenty of condoms with me ... and I have been to the vet recently and am certified one hundred percent grade ‘A’ fresh.”

With that, she leaned in and started nibbling on my earlobe. Oh my. My brain short circuited and my lower brain took control. With our arms around each other, we walked down the hotel corridor to my room. She had to help me with the door key card but had just smiled at my fumbling. Entering the room, I detoured into the bathroom to take a leak. When I finished, I did stare at myself in the mirror for a moment wondering what the hell I was getting myself into.

Before Callie took her turn in the bathroom, she told me to get fully undressed and to get on the bed. I saw that she had the extra sheet folded and spread out on the beds surface. I spotted a small bottle of oil near the clock radio, which was already playing soft music. Her phone was connected to the radio so it was her own playlist. The room lights were off except for the desk lamp in the far corner. I undressed and waited on the bed as instructed.

After a few minutes, she exited the bathroom and carefully hung up her dress. She was wearing a black demi-bra and a tiny thong. Oh my God she was hot. She just winked when she caught me staring at her body. She then turned around and bent over without bending her knees and got a few condoms from her small handbag. I was presented with a perfect ass and the gap between her thighs must have been over an inch. I had to force myself to keep my mouth closed. She sauntered over to the bedside and set the condoms on the night stand.

“We’ll only need those for the main event Hun. I received a text earlier that you are also certified grade “A” fresh. That means we can have more fun playing!”

That information must have come from my clinic visit earlier. The testing must have included an expedited test for sexual transmitted diseases. That my medical information had been sent to Callie beforehand also said that my ‘testers’ knew what would likely be happening here tonight. Either they were testing my morals or my impulse control ... both of which I was about to fail big-time. Or they did not care about what happened here tonight and all would be well. Regardless, I had already made up my mind. Full speed ahead!

I watched Callie slink around the room for a bit. She was so fine. Her taut abs and firm thighs showed that she regularly worked out. I did not see any signs that she used or abused drugs, which was a relief. She also was either a great actress or loved her work as she looked to be enjoying herself. Her fragrance was heady. Some variation of jasmine. I was starting to respond.

“Roll over Hun, I want to start on your back.”

I did as she asked and assumed that position. Callie left me waiting in anticipation for half a minute before beginning to work on my feet and legs. She proved to be an excellent masseuse and hit all the right spots, slowly working her way up my legs and thighs to begin to knead my ass. Her hot firm thighs were straddling my legs, as she dug in with her hands kneading the muscles of my lower back.

Callie moved up and worked over my back and shoulders. She was now saddled on my ass and I could feel her hot mound rubbing across my lower back as she worked and stretched to reach my upper shoulders and arms. Occasionally she would lean down and rub her chest on my upper back. I could feel her hard nipples dragging across my flesh. I was simultaneously feeling relaxed from her massage and excitement from her sexual advances. She finished up on my back and arms and concentrated on my neck. After a few minutes of that she moved to climb off of me.

“Now roll over onto your back Hun. Let me see what I have to work with now that you are fully ... engaged,” she said with a husky voice.

I did as she asked. She smiled a real smile and licked her lips as my proud manhood sprang into view.

“Very nice. That should fill all the right places.”

I had nothing to be ashamed of. While I was not a freak or a ‘trophy,’ as we called in back in the gymnasium locker rooms, I was easily above average and my pecker had served me well over the years. I wish I could say the same about my slight paunch. Even though I kept busy doing physical work, my love of beer had led to a bit of a beer gut. I was glad to see that Callie paid my larger, upper bulge no mind. She moved back down and started on my feet and legs again.

Now I could watch her as she worked. Her demi-bra had been removed and her firm breasts heaved and glistened with a combination of the massage oil and a slight sheen of sweat from her exertion. The room was too dim for me to easily make out the treasures between her legs, but I suspected I’d find out about that area soon enough. Her face was serene and focused as she concentrated on molding the muscles of both legs. Soon, she moved up to my thighs and began working those areas.

I had to widen my legs a bit as she focused on one and then the other thigh individually. Her strong hands wound around each of my upper thigh muscles in turn. Occasionally she would massage my balls and my taint as she passed her hands down those areas. I would moan each time she did. My cock was rock hard and standing proud.

“Hun, your cock is so hard and beautiful. Do you think you can get it this hard a second time? I want to taste you, but I also want to feel you inside me later.”

She had stated that carefully with her husky voice. I caught that she was politely asking me if I had erection issues. That would not be a problem tonight. Twice for sure. It had been a long time since I had gone for three, but I was game to try.

“You are so hot babe that I don’t think that will be a problem.” I replied.

“Oh good!” she said and then proceeded to take me into her mouth more than half way to the root.

Oh my God that felt good! I closed my eyes, laid my head back on my pillow and let out a long groan. My cock throbbed but I somehow kept from shooting instantly. She slowly applied suction and brought her mouth back up my shaft, teasing the underside of the crown with her tongue for a bit before letting my cock’s large spongy head pop out from between her lips.

I opened my eyes and looked back down at her with amazement. She was staring back at me with a lusty smile. After I had calmed a bit, she did another plunge. This time was even better, and I almost came. My toes curled and my hips slowly rose as her mouth moved up my shaft, trying to prolong the contact. All too soon I popped free.

“Callie, I don’t know if I can last through one more of those,” I gasped.

“Well, let’s make it count then shall we?” she replied.

She grabbed the base of my cock firmly and began to jack me off. As she sped up, she lowered her head and began to suck vigorously while swirling her tongue around the underside of my sensitive cock repeatedly. I groaned again and felt myself quickly building to climax. As I tensed my hips she sped up her hand and mouth actions even faster.

Suddenly, I was there. I jammed my hips up as high as I could as I came. My first jet of semen hit her deep in the back of her throat. She continued to jack off my cock as she swallowed quickly. After the third spasm, she removed her hand and plunged her head downward, forcing my cock past her tonsils and embedding it deep in her throat.

“Oh my God!” I yelled out. No woman had ever done that to me before. My orgasm stretched on even longer and I gave her two more good jets before I was reduced to simple spasms of pleasure. I felt her throat muscles working hard, both massaging my cock and swallowing the remains of my spend. When my spasms finally died down she slowly pulled off of me, maintaining suction until, with a final pop, she was completely off my cock. I just lay there staring at her in amazement.

Her smile seemed real as she slowly crawled up my chest ... her hard nipples dragging lines up my torso. When she was even with my head she asked, “Did you enjoy that Hun?”

I surprised her when instead of answering I grabbed her head and kissed her deeply. She stiffened for a moment before giving herself to me and returning my kiss.

“I’ll take that as a yes,” she said when we finally broke apart.

“Yes. It was amazing. You are amazing. Thank you.” I replied.

She laid her head on my shoulder for a minute as my breathing slowed.

“Some men won’t kiss me after I do that,” she said quietly.

“I don’t have any latent fears of being gay so it does not bother me. Besides, you deserve respect for how good you made me feel. I hope to return the favor shortly, “I said.

“Good!” Callie said as she moved back down and straddled me to resume her massage.

This time she concentrated on my abs and chest. She scooted up further as she moved to my neck and upper arms. I could feel the heat of her sex on my stomach. When it looked like she was nearing the end of my massage I reached down and cupped her tight ass with both my hands and pulled her further forward. Now, my head was between her thighs and her wet thong was inches from my nose. I reached up to fondle her tits as I kissed and nibbled on her inner thighs.

It was her turn to give out a moan or two. She slowly inched her way further up until my nose was buried in her mound. I nuzzled her silky covered hot area and tongued the wet fabric of her thong. Her smell was intoxicating and I inhaled deeply, savoring the scent. She reached down and pulled her thong to one side and pressed her hot slit against my lips. I got to work and laved her sex with my tongue. Her nipples seemed to grow even firmer under my fingers. I gave them a slight pinch and she gasped and shuddered a bit.

“Hun! Right there! You got it! Keep going!” she husked.

I did my best to bring her off with just my mouth. Her hips were moving back and forth grinding her sex onto my lips and tongue, the speed and force of her movements quickening. I did not have too much freedom of movement so I did the best I could to keep up. Suddenly she stopped and climbed off my face.

“I’ve got to get rid of this damned thong!”

I watched her quickly strip off the skimpy garment and toss it towards the TV. She then spun around and crawled back on me, this time with her head near my cock and her cunt and thighs surrounding my head. I grabbed her ass with both hands again and forced her cunt onto my mouth.

“Ohh Hun! That’s it!” she gasped as I went to work on her clit with my lips. As she ground herself on my face, I worked two fingers down and plunged them into her channel. She was sopping wet and ready.

She quickly took my half hard cock into her mouth and plunged down, again taking me to the root. Her hips were bucking as I continued to work away. She tried to keep up on my cock but soon pulled off to lay her head on my thigh gasping deeply as her climax caught up with her. I felt her shudder and her cunt squeezed my fingers. I kept up the suction as her juices poured from her faster than before.

After a half dozen good spasms, she rolled off of me saying, “Enough! So good!”

We lay there catching our breath. I was happy I had brought her off. It had to have been real as I doubt anyone could have faked such powerful internal muscle actions. Soon, she rolled around a bit and resumed her attentions on my mostly hardened cock. Her nipping and lapping at it brought it awake and her slowly working hand quickly had it back in working order.

“Are you ready to give me a good fucking Hun?” she asked with a smile.

I just answered by reaching over and grabbing one of the condoms. She took it from me and did the chore of getting it rolled in place over my shaft. When it was fitted Callie quickly spun around and impaled herself on my cock, taking me with one slow and steady plunge.

“Oh yeah,” she hissed.

“Uuggg!” I grunted.

She began to rock her hips. Her arms were on my chest and began playing with my nipples. My hands returned the favor on her tits for a bit before settling down around her hips, guiding her movements. She looked so hot as she worked away on my body. Sweat was covering both of us and we were both breathing deeply enjoying the sensations.

Soon, she moved her legs and I felt her feet straddling my knees as she found a position which gave her better leverage. She began to work her hips faster and added a few inches of up and down thrusting. The condom and my previous ejaculation had given my cock staying power and I just watched her working hard to pleasure the both of us. After a few minutes she saw my smirk and rolled off.

“Your turn to work it for a while Hun. Get busy!” she said as she assumed a sexy pose, presenting herself to me on her knees with her ass in the air and her upper torso lying flat on the bed. I rolled over and got up and knee walked my rigid cock towards her delicious target. She looked so hot and inviting that I stopped and dropped into position to bury my face in her snatch from behind. She grunted as I sucked on her cunt and clit, thrusting her hips back against my face. I quickly felt her hand move up and begin quickly strumming her clit.

“Oh Hun! You are doing everything right tonight!” she gasped. After a minute she hissed, “Get that cock in me and get back to work!”

I felt her finger action continuing on her clit as I stood up and slotted my hard latex-covered shaft into her pink moist channel. I pushed into her steadily all the way to the hilt, making her huff as I filled her with my seven hard inches. When I bottomed out, I pulled out quickly and gave her my full length again, this time a bit faster. Her frigging motions on her clit sped up even faster and she started moaning continuously. I kept up my steady impalement and retraction but quickened the pace and the force of each full deep thrust.

“Oh Hun! I’m getting close! Give it to meeee!”

I began thrusting as fast and as hard as I could. The room rang with the smack of my hips and balls striking her ass. I felt the tingle of my own orgasm nearing just as her cunt began tightening around me.

Her ass suddenly thrust back at me hard as she shrieked out a loud, “YES!”

Her rapidly spasming cunt triggered my own orgasm and I roared, burying myself inside her and filling the condom with my second load of the night. After my thrusts and spasms died down I collapsed forward on top of her hunched-up ass. She was also in the last throes of her orgasm and reached back to tap my hip with her free hand.

“Good job stud! It does not get any better than that,” she panted.

I had to agree. I rolled off and collapsed beside her totally spent. My age had caught up with me and I was exhausted. I had a smile on my face though and ignored the thought of the aches and pains I would feel in the morning. Callie had also rolled onto her side and was facing me.