As I exited the plane, I felt a new sense of excitement rush over my body. I had spent so much energy debating my parents about why I didn’t want to spend the summer on Martha’s Vineyard that I had forgot that it wasn’t all that bad of a proposition. Besides the fact that I didn’t know anyone there and all my friends were working in New York for the summer, Martha’s vineyard was a dream locale for a 18 year old kid trying to waste away his days in the summer sun. My Aunt Kay had a beautiful house on the beach and I didn’t have to get a job or listen to my parents bitch about how lazy I was all summer. In a way, stepping off the plane I felt rejuvenated about the whole idea and I hoped it would be as fun as Aunt Kay argued it would be over the phone.
Kay was my favorite aunt. She was my father’s youngest sister and the proverbial “cool” aunt in my family. In her twenties she was a highly sought after artist and began socializing with an elite crowd that appreciated her work. She amassed a healthy fortune selling various paintings and sculptures; some of which were bought by celebrities. I always loved hearing her stories of the posh parties in upper Manhattan lofts that she attended. She would talk about people she met and the places she’d been.
Kay told me on the phone that she would be in the city for a few days but she would arrange to have me picked up. I saw a man holding a placard with my name on it and I went over to introduce myself. He handed me an envelope and showed me to his car. I sat in the back seat and read the letter Kay had written for me. It read:
“Adam, I won’t be back till Tuesday but James will show you where the key is hidden. Also, James lives just a short ways down the street and is my full time driver who will be at your disposal over the next few days if you so desire. A few notes about the house: your room is upstairs to the right (it has a balcony overlooking the beach) and bath towels are in the closet opposite your room. Kitchen should be stocked if you know how to cook?! Otherwise you’ll just have to do what I do and order in (you can find a few menus under the telephone). Also, the Vineyard is unlike most places you’re probably used to. It is a very “neighborly” place and I usually leave the door unlocked if I’m home. I have many guests/neighbors that stop in from time to time to chat things up or have a drink. Just let them know who you are and accommodate them; you may even meet some new friends. Love you and can’t wait to see you in a couple days! -K”
‘I finished the letter just as James pulled up to the front of the house. It was as grand as I remembered from ten years previous. I immediately went up to my room and began unpacking. James left me his beeper number and told me not to hesitate to call if I had any questions. I finished putting my stuff away and opened the veranda doors to my balcony. I took a deep breath as I admired the sun drenched beach. There weren’t that many people on the beach but then again there weren’t that many houses in the area. Most people lived inland and went to the MV Municipal beach. As I understood it, K owned the beach but let her friends from town go there whenever they pleased. To be honest, the beach looked more promising then I had expected. From my lofty perch, I could see a group of teenage girls sunbathing together, another girl who looked to be about twenty who was gallivanting in a bikini while tossing a Frisbee to her dog, and another really attractive woman who looked like she was laying out with her boyfriend. Definitely some points of interest for a horny 18 year old such as myself.
I walked back into my room and was struck by the sight of a telescope in the corner of the room. I could not resist the hopeless cliché. I wheeled it over and positioned it so that it faced the beach. It was time to check what exactly I was working with. As I peered though the lens, I angled the telescope towards the woman laying with her husband (or whatever). She was lying on her back and I zoomed in on her cleavage. She had a pair of massive orbs that were barely contained in her top. As my uncle use to joke, “Those were three of the biggest tits I had ever seen!” They were at least D cups maybe even bigger. Occasionally she would brush some oil on to her tits, and this made my dick start to twitch, but for the most part she was putting me to sleep. I panned over to the group of young girls who were sunbathing on a blanket. The three girls were around my age, looked to be anywhere from 18-19, and were nothing short of stunning. Each girl was slender and looked to have a least C cup breast. The two brunettes were wearing matching red bikinis and were reading magazines talking to each other. They looked like they were pretty cute but they were wearing big designer sunglasses that shielded most of their faces. The blonde girl was sporting a revealing white bikini and had just returned from a dip in the ocean. I zoomed in on her sexy stomach and panned up to her marvelous tits. The ocean must have been a little chilly because the girl’s nipples were noticeably hard and showing through the thin white material. I felt my dick start to expand and I longed to free my rapidly growing cock from the confines of my jeans. I tore myself away from the lovely view and searched in my bag for a swim suit. MY search was fruitless and my curiosity was calling me back to the telescope, so I was forced to settle on a pair of mesh basketball shorts. I stripped my jeans and boxers off in one foul swoop and quickly jumped into the pair of shorts–stripping my shirt off on my way back to the telescope.
This time I pointed the lens toward the 20 something girl that was playing with her dog. As she frolicked around I watched as her titties bounced up and down. Her body was flawless. She was better developed than the younger girls, and her tits (though not quite a D) were perfectly shaped and proportioned. I also got a great look at her shapely ass. She had a pleasant bounce in her step which made her ass swing from side to side as she pranced about. Every so often she would fix her suit: repositioning her big tits so they wouldn’t fall out and sliding her fingers under the sheen material of her bikini bottoms so she could pull it over her ample ass cheeks.
I had got so caught fantasizing that I barely noticed that one of the young girls had broken away from the pack and was headed up the path to the house. I quickly retreated from my post hoping she hadn’t spotted me. The last thing I needed on the first day was to be labeled a “perv”. I sat in my room contemplating the situation. I glanced out my window but could no longer see the blonde girl. Perhaps she was included in the people that Aunt Kay’s doors were open to. This could be a great opportunity for me to meet some girls who were my age and who I could hang out with this summer. I finally decided I could not sit back and ignore this gem God had dropped in my lap. I waited for my hard on to subside and headed downstairs.
To my disappointment, the blonde girl was not there. The house seemed quiet and untouched and my heart sank. She must have been heading to her car or something. I went over to the bar and fixed myself a drink. A seven on seven with a lime. Just then I heard the outdoor shower go on out on the back porch. I took a long swig of my drink and walked toward the back bedroom. Through the window in the guest bathroom I had a perfect view of the outdoor shower. It was otherwise boxed in by partitions and offered a false sense of privacy. It was a fatal designed flaw that I had discovered when I was a little boy and utilized to spy on my aunts and cousins while they showered. One time I even caught my older cousin Jessica playing with herself after a long day at the beach.
As I reached the window and found a crack in the shade, I was pleased to find the girl in white trying to wash the sand of her body. She rubbed her legs up and down, gently massaging the sand from her body. She bent forward to brush off her feet and I found myself staring directly down at her cleavage–her two tits just hanging there, supported by the elastic material of the bikini top and swaying back and forth as she brushed off her toes. She stood back up and turned around so the hot water was beating down on her chest. For the first time I could see her ass and I was pleasantly surprised to see she was wearing a thong bikini bottom. I had only seen a thong in real life once before (at a strip club me and my friend bribed our way into) and I nearly came at the sight of her bare ass.
I reached down and took hold of my throbbing erection, pulling it out of the mesh shorts and giving it a few short tugs. I worked slow. I was already reaching a breaking point and I didn’t want to cut the experience short, so I stroked my cock very diligently–sometimes stopping to allow my juices to temporarily subside before resuming pleasuring myself.
Suddenly, the girl in the white thong reached back and undid the tie on the back of her bikini top. She let the straps fall to the side and she pulled the top over her head. She was still facing away from me and she appeared to be washing the sand off her breasts, slowly massaging them in the progress. She turned around and let her head fall back into the stream of water. He tits were beautiful. They were perky and as big as I’d thought from my balcony assessment. Her nipples were a pale pink tone that contrasted her tan figure and slightly larger than quarters. I noticed that she didn’t seem to have any tan lines, which meant she was either fake tanning or engaging in the occasional topless tanning session on a quiet day at the beach. The later excited me very much and I wondered to myself if I would ever catch that show from balcony.
I also noticed that the girl’s nipples had become erect. Likely the combination of the cool breeze coming off the ocean and her constant attention to them. The girl rinsed the shampoo out of her hair and soap suds cascaded down her body. I stroked my twitching member faster as I sensed her nearing the end of her routine. I felt the juices boiling in my shaft and I looked for a Kleenex to shoot my load in, but to no avail. Just then I saw the blonde girl reach into her bottoms with her right hand and play with her pussy right in front of me. This sent me over the edge and I immediately busted a huge load all over the window curtains. I would have to clean that up later.
I saw the blonde girl wrap herself in her towel and exit toward the kitchen. I quickly pulled myself together and headed there as well. I casually strolled into the room expecting to catch her off guard and feign surprise myself. When I entered the room I saw her close the fridge and turn towards me. Her towel was wrapped around her upper body, pushing her breasts together. To my amazement, she did not seem all that shocked to see me. Instead she just smiled and said, “Did you enjoy the show?”
My face turned bright red and I struggled to come up with some semblance of words to respond. “Uh, I, don’t think I know what, uh, you…”
“It’s ok. But I saw you in the window. Your Aunt and I spy on the boys when they shower out there. I always look to see if anyone’s watching. So did you?”
“Well I guess I did. I mean I came all over the curtains–my Aunt’s going to kill me. I guess that was a little too much information; I don’t even know your name?”
“I’m Kristin,” her words had a calming effect on me for some reason. I was comfortable talking with girls but I was also extremely intimidated by them. I was still a virgin and I always feared that my lack of experience would be a deal breaker for older girls. Plus I had just admitted to jerking off while I spied on her in the shower. I thought maybe I had already blown my shot. However, Kristin was batting her eyes at me like she took my crude actions as a compliment.
“I’m Adam; I suppose my Aunt told you I was coming?” I stood nervously crossing my legs behind me. I was starting to feel my dick stir again and I tried shift my weight to hide the outline in my thin mesh shorts. “Would you like a drink?”
“Yea, sure, I’m only eighteen but I guess you don’t care. You can’t be more than that either!” Kristin’s statement read more like a question than an observation. I blushed a little but I was used to being called “young looking”. Although I was average size, I had a baby face and people had been underestimating my age all my life.
“Yea, you got me pegged. I’m sorry about spying on you earlier. I guess I got a little carried away because I saw you all on the beach and you looked really good.”
“Oh, so you were spying on us from the beach?” Kristin probed. I swallowed hard again. Why did I keep incriminating myself? “From where? The upstairs balcony?” she pressed. I slowly nodded and avoided eye contact with Kristin. I didn’t know if she was going to see me as a creep at some point. “Well, I want to see too. Show me ok?”
I nodded quicker this time and pointed towards the stairs. She skipped over and I followed her upstairs. The towel Kristin was wearing was short and just barely covered her ass. As she ascended the staircase, the bottom of her ass was clearly visible. I also got a good view of her pussy lips through the thin white thong. She had a slight camel-toe and I could see the outline of her lips. My dick started to get hard and I realized my shorts could not conceal it. I let Kristin hop ahead, hoping that it would magically subside or that she would get over-interested in the view and just not notice. When I finally reached my room, my dick was still rock hard. Kristin was bent over looking through the telescope and that didn’t help matters any; her ass was perked up in the air as if she wanted me to be thinking about what it would be like to fuck her doggy style right then and there. As she peered through the telescope, Kristin swayed her cute butt back and forth slowly and I got the feeling it was a purposeful pose. While she was distracted, I quickly tucked my cock between my stomach and the elastic band of my shorts. Just in the nick of time too because Kristin popped up from her post and gave me a wry smile.
“Hmm, your Aunt told us you were cute but I didn’t expect you would be such a ‘horndog’. You have a pretty good view up here, I can see my two friends Jackie and Emily sunbathing topless out there,” Kristin remarked casually. I took a quick step forward and Kristen started to giggle. “I’m just kidding. Those two prudes wouldn’t dream of sunbathing topless. I think Jackie even wears a bikini when she fake tans in a booth. Me, on the other hand, I don’t mind. It’s better than having tan lines!”
“I agree. I mean I saw you didn’t have any tan lines, I guess with a body like yours there is nothing to be ashamed about,” I said.
“Well it’s nice to be noticed,” she said giggling. “But confidence has nothing to do with it. Jackie has bigger boobs than me she just thinks they should only be exhibited on rare occasions. I think that a woman’s body is one of her few unique assets and I always intend to use it to get what I want. You know what I mean? You have to be willing to work with what god gave you; it’s there for a reason. I mean do you know how many times I’ve gotten in to a club or a bar just by showing the bouncer my tits? Men can be so easy to manipulate,” she said as she looked right at me.
“I guess I can’t argue with that. I’ve done some silly things just to get a girl topless. I once went streaking as part of a dare just to get this girl Amy to take off her bra for me and my friends,” I said trying not to sound too immature.
“Did it work?” Kristen said.
“Well, sort of. Amy chickened out but I did end up hooking up with a girl who was impressed with my stunt. We dated for a little while. She was really my first girlfriend,” I trailed off towards the end because I didn’t want to talk about Sara. We had broken up only about three months ago because I was pressuring her to have sex and I still hadn’t forgave myself for ruining such a good thing because I wasn’t patient.
“Was your girlfriend?” Kristin said while raising an eyebrow. “That sounds like an inconclusive tale.”
“Well she broke up with me,” I said trying to play the pity card. Kristen made a playful frown and I smiled to let her know it didn’t bother me too much. She giggled and took a step closer to me. My dick was so hard that it was pushing willfully against the elastic band and caused my shirt to tent just below my belly button–the outline of my cock brutally apparent.
“Would you streak to see my tits?” Kristen cooed. The words sent a shiver up my back.
“Well, I think we both know that I’ve seen your tits,” I said smoothly.
Kristen glanced down toward my crotch. Her eyes were glued on my hard-on that was sticking up through my shirt. “Well, since you’ve already seen mine…” she paused and bit her lip slightly. “I think it’s only fair that I get to see yours.” Her stare returned to my crotch and I realized that her suggestion was really more of a command.
“Ok,” I said. “Take off the towel and I will lose the shorts,” I knew that it wouldn’t be much of a negotiation. Kristen simply smiled and took a step back. She undid her towel and let it fall to the ground. She put her arms up in the air as to exhibit her majestic body and I took a moment to take it all in.
“I think I’ve completed my part of the bargain,” Kristin said playfully. “Now lose the shorts!” I pulled off my shirt first, my dick was pinned vertically against my stomach and Kristin’s eyes were focused intently upon it. I dropped my shorts and my dick shot out horizontally towards Kristin. She laughed, “That’s a pretty hard cock.”
“Well, I can’t help it. You may be the sexiest girl I’ve ever met.” For some reason, I thought that a compliment was necessary (although my cock was certainly showing its affection). Kristin stepped forward and smiled. Her quarter-sized nipples were rock hard. I couldn’t stop staring at them.
“What are we going to do about this?” Kristin bit her bottom lip again and pointed her index finger toward my rigid cock. Slowly she brought her finger closer until the tip of her finger and the tip of my engorged member met. I twitched slightly in ecstasy and she giggled at my sensitivity. “Did Amy ever suck on your dick?”
I shook my head no, which wasn’t true either (she had blown me a total of three times) but I was still trying to play the sorry dumped boyfriend. Before I could even formulate a sentence, Kristin had dropped to her knees and was examining my dick.
“Looks pretty good Adam,” she said very scientifically. “You have a nice dick. Does Amy tell you that?” I shook my head softly. “Oh she should have. It’s so big and thick and so smooth and well groomed, and I guess we know you don’t have any problems getting it hard! What is this thing, like seven or eight inches? Amy doesn’t know how good she had it,” she said as she reached out and wrapped her small hand around my throbbing member. I was glad I had trimmed the few pubes I had the night before and that Kristin was pleased with my work (even I had to admit I did a thorough job)”I’m going to give you the best blow job of your life!”
I closed my eyes in anticipation. Soon I felt Kristin’s soft lips touch the very tip of my cock. She let my cock gently part her warm, wet lips. Her moist lips felt almost lubricated and allowed my rod to slide effortlessly into her waiting mouth. As her lips moved from the head of my penis to the shaft, Kristin stopped and wrapped her lips tightly around my girth. She begin to suck intently, in long accented bursts in which her cheeks would cave in slightly as she sent a powerful sucking sensation through the tip of my cock. This was certainly a girl who learned to suck dick by practicing on popsicles. She was sucking on the head of my cock like it was candy.
Just then I felt a cold hand fondle my balls. I jumped a little but was pleasantly surprised to see Kristin’s left hand had started to play with my balls. Her right hand was still positioned at the base of my cock and she began to slowly jerk me off as she continued sucking on the head of my dick. Then Kristin took both of her hands and slid them up to my stomach. She continued to suck, going slightly deeper–about three inches down–all the while caressing my body with her hands. Then I felt her hands reach around my body and take a firm hold of my ass. The move caught me somewhat off guard and I opened my eyes to look down at her. Kristin looked me dead in the eye and slowly began to engulf the length of my cock–using her hands on my ass to encourage me to push it further down her throat. When she had almost six inches stuffed in her mouth she pulled back and began to quickly bob up and down. Each time she would drive at least six inches of my meat down her throat and then pull back sucking the shaft of my penis and letting it slide in and out of her lips at the perfect speed–sending ecstasy down my spine and into my balls. I felt my sack tighten and my cock twitch as I reached my pleasure apex. I reached out and grabbed the back of Kristin’s head and pushed my dick as far down her throat as I could. Kristin took my entire cock down her mouth so that her nose was mashed into my pubic. She took her hands off my ass and grabbed my balls with her right hand. This sent me into a ferocious orgasm and I clutched the back of Kristen’s head as my twitching member shot a stream of jizz down her throat. She seem to be taking it like a pro but eventually she gagged and she pulled back using her right hand to pull my dick out of her mouth. After she caught her breath, she put the tip back in her mouth and sucked out the rest of my juices. She swallowed some of my cum and spit some of it back on her tits. She took my dick in her right hand and started to rub the tip against her cum covered nipple. Just then I felt a final twitch and I shot one last creamy shot all over Kristin’s tits.
She giggled and released my cock. “Guess I’m going to need another shower,” she said as she wiped my sticky cum off her tits. “Your still hard huh?”
I looked down at my dick. It was dripping with saliva and cum but at it was still rock hard. I guess I had just had a lot of sexual energy that had been stored over the last few months. I shrugged my shoulders at Kristin and she hopped up off her knees.
“I’ve never been one to waste are hard dick. Come over here” she said and she walked over to my bed. Kristin pulled her bottoms to the floor and turned around to face me. She had a very sparse bush that was shaved into a neat triangle. “Do you have a condom? I’m clean just a policy I like to keep so that I stay that way.”
“I don’t,” she frowned at my response. “But listen, I’m a virgin. You don’t have to worry.”
“A virgin you say? Well this keeps getting better and better,” Kristin said smiling. She took a step backwards and hopped up on the bed. Her legs were wide open and she motioned with her finger for me to come closer. As I reached the edge of the bed, I took my position between her legs. Kristin had slid her pussy to the edge of the bed so that her sopping cunt was easily accessible. I was almost shaking as I got nearer to her. She had her eyes closed and her arms flat on the bed over her head. I stepped up between her thighs and positioned the bright red helmet of my cock against her slit. I couldn’t believe I was about to fuck for the first time. I rubbed the tip up and down her slit. I wasn’t really sure how to put it in. “Oh don’t tease me,” she said. “Fill me up you virgin!”
With Kristin’s encouragement, I plunged my dick deep into her warm tight pussy. Kristin let out a brief expression of pain but that soon turned to pleasure. Her eyes were still closed and she took a deep breath and let out a sigh as I started to move in and out slowly.
“Faster, Adam. Do it faster,” she said. I grabbed her thighs and began working faster with an established rhythm. I bucked my hips and she moaned each time I drove my manhood back into her wet pussy. “Oh, it feels so good inside me. Fuck me baby! Fuck MEeee!”
Hearing her plead with me made me bust my load right there inside of her. I knew that Kristin felt the warm juices inside her cause she opened her eyes and smiled. Even though I didn’t think it was possible that I had any sperm left in my body, I didn’t want my first sexual experience to be so short and pathetic. I decided to push on and I started to stroke my cock in and out once more. Kristen bit her lip to acknowledge my effort and started grinding back and forth in accordance with the rhythm of my thrusts. I reached down and groped her jizz covered tits.
Kristin moaned as I played with her boobs. I gave equal attention to her breasts and areolas, occasionally dipping down to suck on her aroused nipples. I noticed a change in her breathing pattern as she started to pant and her moans became truncated as she neared her orgasm. “Oh, that’s it. Don’t stop, oh, oh sweet Jesus, ohhhHH!” I felt Kristin’s pussy shudder and the warm wet sensation of her juices as I completed a final stroke and collapsed onto her naked body. I left my dick inside of her and whispered into her ear, “thank you.” She giggled and gave me a kiss. My hard on subsided and I pulled my soft, overworked, penis from her drenched pussy. I felt exhausted and I rolled over to lie next to Kristin. She was already asleep. I just stared at the ceiling, occasionally glancing back at Kristin’s sexy nude figure, and wondered what other fantasies I might fulfill this summer.