My hand went through the screen like butter and nobody was more surprised than I. It wasn’t what I expected to be doing at 1:30 AM on that warm Caribbean night. But Bobbi, bless her soul, had managed to tease the villa number from the young concierge who couldn’t stop staring at her half-open blouse and the large breasts bulging from it. It had already been a long night.
I’d only met Bobbi a few days ago when I first arrived at the resort. She was prowling the beach and the little bar at the palm-treed end of it in a killer white bikini. We chatted a bit over grilled chicken and pina coladas before she wandered away with a lovely sway to her hips that told me she knew I was watching. She picked me up at the main nightclub that night and we had been at it hot and heavy each night. For what ended up being the cost of her meals and drinks, we had a pretty good arrangement. She liked older guys with lots of money as much as I like women who can make me crazy.
I’m not sure what she did during the days; I likely don’t want to know. But I met Rich and Jessica at the pool yesterday afternoon while Bobbi was otherwise engaged. One look at Jessica and fuck, I wanted her so bad. She had the kind of look and the body that makes me hard just looking at her. Complicating things was her tiny--and I mean tiny--black bikini that was not only a size too small for her ample body but didn’t cover her existing tan lines. They had just arrived and her bags had been lost en route. The little black number was all she could find in the gift shop. Or so I found out later.
She and I made eyes at each other across the pool while her husband completely missed the proceedings. I took a drink over to them both and I could tell there was a chance I’d be able to be with her at some point. The way she tossed her head and brushed her hair aside and her body squirmed was enough to give me a hint of what might lie ahead. Rich was polite and very nice but he had no idea. We chatted for quite a while and I invited them on a private snorkelling charter for the next day. We agreed to meet for a drink after supper to talk it over.
At supper, I told Bobbi I would be busy that night but she insisted on coming along. She knew damn well I was on the prowl. She told me to meet her in the nightclub after I met the new kids.
I nearly died when I saw Jessica walking in with Rich to meet me after supper. She had on a short tight skirt, heels, and a tight tiny top that it turned out had also come from the gift shop. Drinks went too well and Jessica and I played a bit of footsie while we drank and chatted. When Jessica found out I was going to dance she begged Rich to take her there too. He agreed to come into the nightclub to give Jessica a chance to dance for a bit. That’s when Bobbi swooped back in and acted like she had known me forever. She fawned over Rich and dragged him to the bar in the club while Jessica and I hit the dance floor.
Bobbi was good; she put him on a bar stool and practically sat on him. She ordered drink after drink for him while she flirted intently.
It's a story of its own but in less than an hour, Rich was plastered and drooling over Bobbi and I had Jessica behind a partition at the back of the club with her arms around my neck and her legs around my hips. I lifted her and felt around with the head of my cock until I hit her burning wet pussy and she hugged hard and whimpered as I Iowered her down and impaled her. I came faster and harder than I wanted, but fuck she felt good. So fucking good.
We straightened up and Jessica wiped up the cum seeping from her pussy with what was left of her silky panty. She dropped them to the floor when I danced her back out of the dark into the semi-dark of the dance floor. She was giggling and biting her lip as we approached the bar where poor Rich was much the worse for wear. Bobbi had her hand on his thigh or crotch and he was leaning on the bar on one elbow with his face about six inches from her cleavage.
Never much for self-control, I had my hand up under the back of Jessica’s skirt and my fingers in her wetness while Bobbi got Rich mobile. I promised her if they still felt up to it I’d take them out for the charter today. Jessica seemed a bit confused about Bobbi when she put her hand up inside the back of my shirt but she had her hands full with Rich.
We helped them out to the path to the villas where Jessica said she would be okay from there. Rich was managing to stagger along while he leaned on her.
Bobbi pinned me to hedge and put her hand down my pants. She fondled my semi-soft cock and squeezed it a few times. It pounded back up to hardness. She lifted her hand to her face and inhaled deeply. She smiled an evil smile and kissed me hard. “I knew if you got the chance you would fuck her,” she whispered in my ear. “You better have something left for me!”
I laughed and pushed her off and headed for the dance.
During the third dance, she stopped mid-beat and pulled me to the wall. “For fuck sake, are you that distracted?” she asked in response to my less than fully committed gyrating with my white man’s overbite.
I shrugged my shoulders and laughed. “I can’t help it, that girl is sweeter than honey, and so innocent …” I trailed off.
“Compared to me?" she hissed. But her smile told me she wasn’t exactly heartbroken.
“Idiot,” she intoned and taking me by the hand, literally dragged me out and down the path to the office area.
She planted me in the darkness outside and went in to speak to the concierge, a young local guy in a shirt that was at least a size too big. It took her ten minutes of looking, leaning, chatting and touching his hand and forearm to get the villa number.
Giggling, we headed back down the path to the villas.
Theirs was almost totally dark but there was light coming from one sliding glass door. Bobbi moved further off in the darkness while I approached the door. It was the bedroom.
Rich was flat out on the bed, passed out or asleep already. The light was coming from the bathroom. Jessica was not to be seen but in a few minutes, she came out of the bathroom in a towel, fresh from the shower. She flipped off the light and turned toward the bed and the sliding door beyond. She jumped and gave a little shriek when she saw my silhouette in the doorway. I was leaning on the door frame with my hands on the top rail spread far apart. Rich didn’t move. It took her a second to realize it was me. She paused for a full minute. My heart was pounding out of my chest and my cock had pounded back up to full hardness in my pants. My shirt hung open.
Ever so slowly she approached with her arms wrapped tight around the towel. When she was close enough to make sure it was me she glanced at Rich and wiggled his foot. When he didn’t respond, she slowly approached.
My hands slid down and pressed on the screen door as she reached the glass door on the other side. She looked down and slowly opened the towel, then shook her wet hair and looked into my eyes, less than a foot away. She dropped the towel and put one hand on the glass right in front of my right hand. Eyes locked, she slid her hand down her tummy and hooked a finger up into her pussy. She bit her lip.
Nostrils flaring, I leaned my body on the screen. She lifted the hand from her pussy and sucked the finger into her mouth. Her body gyrated slowly. As she sucked her finger deep into her mouth she leaned her breasts against the warm glass and ground around in the wetness from her body.
Fuck. My cock was pounding and I could barely breathe.
Glancing over at Rich again, she looked down and unlocked then opened the glass door. She flicked the lock on the screen door when I tried to slide it open. She moaned out loud and her hips rolled and she squeezed her nipples and pulled gently on them. Her mouth was open and she tongued her upper lip as she leaned close to the screen.
That’s when I lost it. I thrust my hand forward and it easily split the screen. She gasped and put her hands to her mouth. I grabbed the two sides and ripped it open in a single swipe.
Growling I reached in and grabbed her by the back of the neck. Dragging her out I held her with one hand and fumbled with my pants with the other. She took over when it took a few seconds. She quickly opened them and pushed them off my hips as she sank down in front of me. Purring.
She took my cock and rubbed it over her lips... moaning … “Mmmm, I can still smell us ...” She licked the head. “MMMMM, and taste us ... mmmm.”
I wound my fingers in her hair and tried to pull her onto my cock but she pushed it up against my tummy... smiling up at me. She turned her head and pressed her lips along the bottom of my shaft. She ran her mouth up and down while pressing on the fat vein up the bottom of my cock. I groaned loudly. I half turned and collapsed against the wall and she took one step on her knees and pressed her breasts on my thighs.
Returning to the vein, purring more, she licked up and down before settling in and licking and sucking where the shaft stopped and the head of my cock started. I groaned again. “Oh fuck, yessss.”
She lapped at the underside of the head, then sucked on it. Not taking it in her mouth, just her lips sucking on the bottom side. I was going out of my mind, eyes closed, head tilted way back.
When she finally sucked the head into her mouth I opened my eyes to see that Bobbi had moved to within about five feet of us. She was standing with her feet apart, her hand up her light black skirt, clearly fingering her hot pussy.
A couple sucks on the crown of my cock and it was again too much for me. I shot a load of hot cum into Jessica’s mouth. She sucked and sucked on the head, one hand on the shaft and the other fingering herself. She moaned louder and louder on my cock, then started rubbing it all over her face while she squealed out an orgasm of her own. Bobbi was crouched down hugging her knees, clearly having had her own little death.
I lifted Jessica up and her arms locked around my neck and we kissed and kissed and kissed. She put me inside her and I could feel her pussy squeeze me repeatedly while she moaned into my mouth. Her hips rolled and bucked against me.
Bobbi rose and staggered into the darkness while I lowered Jessica. My semi-hard cock dragged out of her pussy and up over her clit. A rasped intake of breath and a gasp and she pulled her hips away to break contact. I held her with her body against mine for a long time. Our hearts finally started to slow. I took off my shirt and put it over her shoulders. She moved inside the door, leaned out for one more kiss, then slid the glass door between us. She leaned on it again, her breasts flattened and I put my chest against the glass on my side.
“Come on, Valentino, for fuck sakes!” Bobbi whispered from the dark. I turned and laughed and ran toward her in the darkness.
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