Poor Rich Boy

Posted in: Chance Meetings

There’s a place I like to go. It’s a laid back place with a mixed crowd of bikers, boat dwellers, and folks just enjoying the drinks and food. It’s also a great place to meet people. I decided to take in the atmosphere one evening since I didn’t have any plans to speak about and hang at the bar instead of the table tucked in the corner where I usually sat. I also felt like being provocative wearing a sexy little black leather skit just long enough to hit the top of my thighs, a crisp white button down blouse with the top buttons undone to show off the swells of my breasts and my highest come hither black heels. Getting dressed that evening I chose a cute lace black bra that pushed my D cups up nicely, black lace boy briefs that I’d always found sexier than a g-string up my crack and just enough of my imported perfume to leave an impression. I looked in the mirror pleased with how the lace hugged my hips; the swells of my breasts well rounded and checked the back view to see just enough of my firm cheeks below the lace.

“The place is lively tonight” I mused as I found a seat at the bar and slid on the bar stool crossing my long legs. “What will it be darlin” the bartender said with a flirtatious smile. “I’ll have a vodka martini extra dirty” I said returning the smile. My eyes perused his body as he turned to make my drink. “Not bad” I thought to myself. I’d always found him attractive. He returned with my drink, and started a tab. I checked out the regulars as I sipped my drink. A couple of older bikers laughing it up with their women, an older woman nursing a gin and tonic, and three younger guys at the end of the bar talking and laughing loud. They looked to be about 25, 26 years old two in jeans and t-shirts and the other dressed in white. The one in white looked like he just stepped out on shore leave and seemed to be the one spreading the wealth around for his friends. I discretely checked him out; he was about 6 feet 2, clean cut dark brown hair, hazel eyes, broad shoulders, muscular thighs and a cute ass. I wondered what he looked like nude and smiled to myself. I chatted with the folks at the bar listening to tall stories and life in general. I had just finished my third martini when the bartender brought me a fourth “From the guy at the end of the bar” he said and winked. Looking to the end of the bar I saw the guy in white staring at me. I tipped the glass in his direction as a thank you and he flashed a gorgeous smile making his way down the bar. A little unsteady on his feet, he swaggered next to me while his friends snickered and teased “Man she’s not going to give you the time of day” one said. “Dude get your drunk ass back down here and leave the lady alone” the other said as they roared with laughter.

“I thought I would buy the sexiest woman in this place a drink” he said. “Wow does that line work all the time” I laughed. “That skirt of yours is barely there” he said leaning on the back on my chair. “Maybe you should sit down sailor” I said flashing my sexiest smile at him. He managed to climb on the bar stool and not hit the floor his friends were doubled over with laughter slapping each other on the back. “Ignore those idiots. My name’s Jack” he said shooting an annoyed look in his friends’ direction. I caught him staring at my tits and gently placed my fingers under his chin guiding his eyes to mine “Nice to meet you Jack. I’m Jessica”. He blushed awkwardly and stole another glance down my blouse. “I’m serious you’re sexy. You must be waiting for someone right?” he asked looking disappointed before I even answered. I assured him I was on my own tonight just out for a few drinks.

The night went on and we flirted with each while he vacillated between me and his friends. Feeling his liquor he started to sing a little off key to the music playing in the bar; wrapping his arm around my shoulders to keep his balance. It was very cute but I thought “he’s a little too drunk, too bad”. His flirting became more adventurous gliding his hand up my thigh, stealing a kiss to see how far he could get with me. Jack was hard to resist and I returned his boldness. Finally his friends feeling a little left out said their goodbyes leaving to look for fun elsewhere. One of his friends stopped next to me “take him home will ya? Don’t want him falling in the drink”. The bartender overhearing assured them Jack would be looked after. I actually didn’t realize how drunk he was until then his shirt tail hanging out the back of his pants, his hair falling into his eyes and cheeks blushing from drink. Hot from our flirting I still couldn’t bring myself to take advantage of him. I decided it was time for me to head home and leave him alone. Maybe I would stop by that club I wanted to check out and find a play toy that wasn’t as drunk. I got the bartender’s attention to pay up my tab and Jack slapped down cash before I could grab my purse. After a little good natured arguing I agreed to let him pay, kissed him on the cheek saying my goodbyes. He stood there looking totally devastated trying not to waver. I slid off the bar stool and gave him a hug. His body was warm and his heart beat strong, as he wrapped his strong arms around me. I pried myself out of his arms “this is so wrong I got to get out of here” I thought as I walked towards the door half heartedly trying to convince myself. Jack shouted “later” to the bartender and was right on my heels. “Look sailor you’re a little drunk and I really need to get going” I said trying not to sound like I was rejecting him. The bartender appeared in front of Jack trying to convince him to wait; someone would get him home but Jack was not buying it. He wrapped his arm around my shoulders “she’s going to take me home man” he slurred. The bartender gave me a questioning look and I could see concern in his eyes. “Jack must come here all the time. First time I’ve seen him” I thought. He was such a sweet, helpless guy I couldn’t say no “where does he live I’ll drop him off and make sure he’s in alright” I said to the bartender. “He’s got a boat on the docks next door. It’s walking distance” he told me.

“Alright sailor lets go. I’ll tuck you in and then I have to get going okay” I said to Jack. He grinned and wrapped his arm around me tighter. “We’re both going to hit the pavement” I thought to myself smiling. We went outside; the cold sea air filled our noises and kissed our faces. “You have a boat?” I asked Jack making conversation. “Yeah I live there after my parents kicked me out of the house” he said. “Jesus how old are you really?” I asked. “I’m 22, old enough” he said as I struggled to keep him upright in heels. “Why did they kick you out” I asked. “Because I have no aspirations and keep fuckin up” he slurred and laughed bitterly. “The boat came with the deal to get me out of the house” He added. We made it to the gated entrance “you have the key” I asked. He reached into his pocket swaying and pulled out the key and his pocket in the process. I took the key from him and slipped his outturned pocket back into his pants. He grabbed my hand and pushed it toward his manhood. I felt a rush of warmth in the pit of my stomach and gently pulled my hand out of his pocket. Opening the gate I took him by the arm and lead him through letting the gate slam behind us. We walked down the walkway and I hoped he remember which boat was his. He looked up brushing the hair out of his eyes “it’s on the end” he said. I looked to the end of the walkway and saw more than a boat or what I was expecting to see. It was luxurious. “At least we don’t have to climb up a ladder” I thought to myself. We reached the ramp and boarded. “What do you think” Jack asked. “It’s beautiful not what I expected” I said. “Yeah my folks have money I get the yacht and monthly expenses from my trust fund as long as I don’t embarrass them” he said moodily. He turned towards me pulled me close and wrapped his arms around me. The warmth from his body felt good against the cold se
a air. “Stay the
night with me” he said looking down at me with his hazel eyes. Still torn I simply smiled at him. He took my hand and led me below deck snapping on the lights and dimming them to a warm glow. We entered a spacious living area with leather couches and dark wood paneling. The d├ęcor was tastefully done; cozy and huge at the same time. He swaggered over to the bar “you want another” as he reached for a decanter of brown liquor. I caught his hand before he could poor a glass and placed the decanter back on the bar “I think I’m a little drunk” I said hoping he didn’t see through my lame excuse to keep him from drinking anymore. He flashed that brilliant smile at me “I gotcha”. “Come on let’s get you in bed” I said and gently pulled his shirt out of his pants slowly unbuttoning it. He stood there looking helpless, his shirt hanging open revealing his chest with soft brown hair, a line of hair trailed down the center of his stomach disappearing into his pants. I brushed my fingers through the hair on his chest and traced the line down his flat stomach. “There was no way I was leaving” I smiled to my self. Slipping my fingers into the front of his pants I led him to the couch and he slid down into the leather his long legs stretched out in front of him. Getting on my knees I slipped his shoes and socks off and then looked up at him my hair falling over my eye. A moan slipped out of Jack as he looked down at me and my eyes fell on his crotch to see that he was fully hard underneath his pants. I stood up and straddle him sitting on his lap, slipped him out of his shirt and kissed him. He ran his fingers through my hair as we kissed. I could feel his cock hard between my legs as I felt a warmth intensify between my legs. We kissed for what seemed like a long time, exploring each others mouths, Jack sweetly kissing my chin, the tip of my nose, and back to my lips. He pulled back from our passionate kissing “You never answered my question”. “What question was that” I replied coyly. He brushed my hair back with his fingers and gazed into my eyes “stay with me” he said. I couldn’t resist he was so passionate not at all what I expected, gentle and sensual. “I’ll stay” I answered as I slowly unbuttoned my blouse and let it fall to the floor. He pulled me close and licked the swells of my breast tracing the lace and sliding his tongue between my cleavage. His hands cupped them and gently massaged my nipples through the lace. I brushed his hair back so I could watch him suck my nipples through the lace as he slid his hand up my back and popped my bra loose.

Jack slid one strap and then the other off my shoulders with his teeth releasing my voluptuous tits as I slipped my bra off my arms and onto the floor. “God they are beautiful” he moan as he licked them and sucked on my nipples. I arched my back moaning gliding my fingers through his soft hair. I was completely wet my hips slowly grinding on his crotch. He placed his hand on the back of my neck pulled me in for a kiss and whispered in a shaking voice “stand up”. I stood up in front of him. He sat on the edge of the couch kissing my stomach and unzipped my skirt. He pulled my skirt down over my hips and let it fall to the floor as I kicked it aside. Placing his hands on my hips he pulled me close kissing my mound through the lace and turned me around. I felt his lips on my lower back and then on my partially exposed cheeks. He licked the back of my thighs as he slid his hand down my stomach and underneath the lace. His fingers moved between my legs to feel how wet I was. His fingers glided over my wet lips as he slumped back into the couch pulling me on his lap. He spread my legs wide with his and I lay back on his chest. His fingers explored my sweet spot, massaging my clit, slipping past my wet lips while his other hand squeezed my tits. Jack placed warm kisses on the side of my neck grinding against my ass and my body shuddered. I squirmed on his lap as he slipped two fingers inside of my wetness slowly sliding them in and out of my juices. His moans vibrated against my ear, my thighs started to tremble as he thrust his fingers in deeper. His hand flat against my stomach Jack held me against his body tight while my squirming and thrusting quickened. Another shudder tore through me, a ball of velvet warm radiated from my stomach shooting through my body as I moaned uncontrollably grabbing my tits and gushing on his fingers. He held me until the trembling stopped. “Jessica you’re so fucking sexy” he whispered as he slid his fingers from between my legs. His fingers glistened from my juices as he brought them to my lips, tracing them softly.

“Let’s go to the bedroom” he said as he lifted me off his lap. I followed him to the bedroom in my panties and heels. He stopped in front of the huge bed and turned toward me. I slid my hands down his stomach unzipped his pants and slid both pants and boxers down to his ankles. I got on my knees guided him out of the tangle of material on the ground around his feet and admired his hard cock. He was so big; ten inches of thick meat his balls big and heavy. I moved closer to him on my knees smelling his musky warm scent and started to lick his balls sliding one into my mouth and then the other. His balls nice and wet I licked the length of his dick letting my tongue trace the circumference of his thick head and then took him in my mouth. Holding the base of his cock I slowly bobbed my head taking him as deep as I could. His girth filled my mouth and my tongue rubbed against the heavily veined underside. He moaned breathing hard as he felt my tongue playing on his dick. My hand explored his firm muscular ass forcing him closer while I tried my best to swallow his cock trying not to gag as his thick head hit the back of my throat.. His trembling moans mingled with the sound of the waves gently lapping against the yacht. Jack gently pulled me off his cock and lifted me to my feet picking me up in his strong arms he lay me on the bed. I kicked off my heels as they dropped heavily to the floor. The reflection from the water through the port holes rippled across his body as he looked down on me with his hazel eyes heavy with lust.

Jack slid his hands under my ass slowly sliding the lace down my hips, to my thighs, to my knees, to my ankles then wrapped my ankles together with my panties and lifted my legs up. He slid his other hand down the backs of my legs slipping his fingers across my wet pussy and down to my anus. He slipped two fingers into my wetness getting them slippery with my juices and then slid his fingers into my ass. I wriggled on the bed as he played with my pussy and ass. Fighting desperately to spread my legs and let him in. My excitement was driving me wild. When I thought I couldn’t take it anymore, he pulled my panties off my ankles and released my legs. I rolled over on my stomach, getting on my knees and lifting my ass in the air. He mounted me quickly thrusting deep into my pussy with hesitation and fucked me hard. I threw my hips back on his dick squirting uncontrollably. He grabbed my hips and rammed me harder. I looked over my shoulder at him fucking me, moaning as our eyes met. “Fucking sexy” he growled. He hammered away at my cunt filling me completely; my moans turning to screams as thick creamy cum oozed out of me. He pushed down on my lower back forcing me to take him to the balls. I could feel his thick head pounding my g-spot and gushed again screaming.

Jack pulled his wet dick out of my pussy, pulled my cheeks apart and pushed his thick head into my anus. The tightness made his body quake as he forced his manhood in my ass snatching my breath away. I collapsed on the bed as he pressed his chest against my back, straddled me pushing my legs together and fucked my ass hard. I gasped for breath, raspy moans burning my throat our bodies slippery with sweat. It felt like he would rip me open but I didn’t want him to stop. Jack started taking long, deep strokes, breathing hard on the back of my neck, pinnin
g my wrists to t
he bed our bodies’ slick with sweat. He pulled back to the head my body jerking underneath him while he tightened his grip on my wrists. “Fuck! Fuck! Fuuuuuuck!” he growled. With one last vicious thrust bringing me to the brink of unconsciousness he shot his hot load in my ass and collapsed on top me. His heart pounded against my back, gasping for air as my body shuddered underneath him and creamy thick cum flowed out of my aching pussy. Jack kept his dick in my throbbing ass until totally spent and soft he slide out. He rolled off of me lying on his back and pulled me on top of him wrapping his arms around me as he closed his eyes snoring softly. I kissed his lips softly, closed my eyes “maybe we’ll do this again” I thought as I drifted off into a deep sleep.

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