Unexpected Fun at Resort

My boss presented me with an all-expenses paid trip to a resort in the Caribbean for being the top salesman for the quarter. Being single and twenty-six year old, this would not have been my first choice as a prize. However, getting away from the Boston winter for even a week would be a welcome break.

When I arrived at the resort, I was given a tour of the facilities and shown to my room. Most of the guests were with a significant other, reminding me that I was alone. I spent the next four days on the beach, eating, and getting a good buzz on each evening. The only single ladies I had seen were either jailbait or not my type. With just one night to go, I was only thinking of how much it was going to suck to go back to snow and negative temperatures in Boston.

As I ate dinner that night, four ladies in their early to mid-thirties were sat behind me. They were obviously college roommates catching up with one another. As I was getting ready to leave they started to discuss their sex lives. Intrigued by the idea of hearing about the sex lives of these ladies, I ordered another drink and decided to eavesdrop. Three disclosed very vanilla sex lives of married couples, the fourth confessed she had only had sex once in the two years since her divorce and that was a drunken episode with her ex-husband.

I figured I had been a voyeur for long enough and headed to the bar for a couple drinks before heading to my room for another night of watching TV and jerking off to internet porn. On the way back to my room I noticed the beach area was lit up. Curiosity, got the best of me and I went down to the beach to see what was going on. A beach party was planned for the evening. My choices were clear, sit in my room and jerk off to internet porn or come down to the beach and have a couple drinks, watch old married white people dance and then go back to my room and jerk off. I decided on option two.

I showered and threw on a shorts and short sleeved shirt that emphasized my toned black biceps. I was thinking I might as well give those married ladies something to fantasize about when they were fucking their husbands tonight.

To my surprise the DJ played a good mix of music and there was a nice crowd. I danced a couple dances with some of the ladies whose husbands were allergic to the dance floor. After a while I noticed the four ladies from dinner dancing together. All were wearing sundresses or skirts. The divorcee had on a sundress with no shoulders that came down to her knees. She was showing ample cleavage and I caught myself staring. There was something about her that made me want to stare. All four were petite and cute in that way ladies get as they age. The divorcee exuded a sexuality that enthralled me, I had to make a move.

After another dance with an married lady, I approached the divorcee and asked her to dance.

"I'm shouldn't." She replied shyly.

"It's only a dance.", I said. Hesitantly, she stood and followed me to the dance floor. We danced several dances and I learned her name was Melissa, she lived in Boise, Idaho, had two children and had been divorced for two years. When a slow song started she tried to leave. Taking her hand in mine I asked, "Where are you going?"

"Back to my seat."

"One more dance."

Avoiding my gaze she nodded and moved towards me. I put on hand on the small of her back and another on her smooth pale shoulder. I started to rub her soft shoulder and pulled her close to me. She looked up at me and I gave her a soft kiss on the lips. She kissed me back then turned her head away. I lifted her chin and kissed her again, pulling her tight to me, feeling her large breasts press against my chest. The kiss turned more passionate until she broke it, glancing over to where her friends sat. I followed her gaze and noticed one was giving her a thumbs up, Melissa blushed and turned back to me and buried her face in my chest as we danced.

I convinced her to sit with me after the song finished. We chatted a little and I placed my hand on her knee, then slowly let it move up her thigh. As my hand neared the hem of her dress she grabbed my hand. I looked her in the eyes and said confidently "Move your hand and spread your legs a little." She did as I asked and I let my hand wander under her dress, teasing her inner thigh, getting close to her panty line but never quite touching it. I continued to talk to her like nothing was going on, I guessed she was growing more excited by how her hips were moving slightly how she bit her lip as I explored her hidden upper thigh. She let out a soft gasp as I ran a finger softly over her panty clad pussy and I said that maybe we should go somewhere more private.

We kissed passionately as soon as we got into my room. My hands wandering over her body and pulling her sundress down to expose her bra. I quickly removed her bra releasing her large pale breasts. I glanced down to admire her breasts and took one in my hand and softly ran my thumb over the nipple. It immediately hardened and Melissa pushed her hips into mine, my cock straining to get free. In a firm confident voice I said "Get on your knees and suck my cock." She looked at me with nervously then slowly got to her knees pulling my 8 inches of hard black cock free.

"It's been a while" she whispered before she started to lick the head and then shaft of my cock. I let out a little moan and replied "You are doing fine." Slowly she took several inches into her mouth. Moving her head up and down slowly. I ran my fingers through her long red hair, letting her control the pace of the blowjob. She looked up at me with her green eyes as her mouth moved up and down my hard cock. Her willingness to please overcame her inexperience and my cock grew harder in her mouth. After several minutes I asked her to stand up. I kissed her again as I slowly lowered her to the bed.

"Spread your legs" I ask in a quiet voice. She obeyed, her legs spread slightly, giving me a view of her trimmed red pubic hair. I stripped, grabbed her ankles, and spread her firm white legs wider. I slowly kissed up her calf, under her knee, her inner thigh, eventually spreading her labia and flicking my tongue over her clit. Melissa let out a soft gasp and grabbed my head.

"OH GOD ", she moaned enthusiastically. I continued to tease her clit with my tongue and inserted a finger into her wet pussy. I felt her pussy clench on my finger as I slowly fucked her pussy with my long middle finger. I continued to please her with my tongue and middle finger, her hips moving, moans of pleasure escaping her mouth. Suddenly, Melissa tensed up said "I'm cumming" and clamped her legs tight onto my head. She shook with her orgasm and let out a little cry of pleasure.

I moved up her body, positioning my hips between her legs. My hard black cock softly rubbing against her pussy. As I started to slide into her Melissa said "Not too hard, it's been awhile." I slowly pushed my cock into her tight white pussy - watching her eyes for clues of when to stop and when to proceed.

Finally, I was fully inside her. Looking into her eyes seeing pleasure but a little discomfort I asked, "Are OK?"

She answered by nodding slightly and running her hands over my toned dark chest.

Slowly I started to stroke in and out of her. With each stroke I quickened the pace, seeing the pleasure build in her eyes. Hard quick thrusts made Melissa gasp loudly while slow sensual strokes made her moan.

She wrapped her legs around me and I moved into a more upright position. Looking down at her breasts sway with each thrust was almost enough to put me over the edge but I help out, wanting to see her cum a second time. Sensing she was more accustomed to my size I started to thrust harder, watching her eyes to ensure I wasn't hurting her. She moaned louder and pushed her hips to meet mine. We developed a rhythm as we used each other's body's for our mutual pleasure.

I stared to thrust harder wanting to put her over the edge. Her pussy tightened on my cock as she came, which triggered my own orgasm. I thrust hard and deep shooting my cum deep inside of her pussy.

My cock slid out of her as I collapsed next to her. She cuddled up next to me, her head resting on my shoulder. Her pale skin and red hair accentuated by my dark skin was almost enough to make me ready for another round.

"That was great" she whispered.

"That was only the beginning" I replies as I ran my fingers through her long hair.

Based on the response I will write another chapter to this story or let it die where it ends.