I didn’t have my first date until I was sixteen, and THAT went horribly. I wouldn’t have a second date until I was coerced into asking a girl to Senior Prom, and THAT made my first date look like a roaring success. So, by eighteen years old, I still hadn’t kissed a girl, beyond a quick peck hello in greetings. At nineteen and twenty, I managed a few dating experiences and was told I was a good kisser. That led to a few semi-sexual encounters and eventually a one-night stand on a drunken evening in college. So, by the time I moved out to the Hamptons for my summer work as a fishing guide, I was no longer a virgin. But I was about as inexperienced and awkward as a non-virgin twenty-one-year-old could be.
Around women, I was a total mess. On the rare occasion I gathered the courage to ask a girl for a date, I had no idea what to do. I was a nervous wreck and acted like the quintessential nerdy kid in the Rom-Coms that make me cringe. That left me extremely sexually and emotionally frustrated. I loved being around women. I loved talking to women. I also loved touching women. Now you can see where frustration would set in.
The good news was that my job had me working on boats. I was always a different person around boats. Even as a child, when Dad took me fishing, I would confidently decide where and how to fish, as well as most other aspects of our fishing day. A shy, timid kid on the street - a confident, outgoing man on the docks. That personality worked extremely well for me in my job and created an image of someone that my childhood friends never knew.
Starting early in June and lasting throughout the summer, and well into fall, I would be working on boats nearly every day. I worked long days, usually starting before dawn and ending late in the afternoon or evening. After my fishing trip of the day, I would either hang at the marina bar or, if it was early enough, in the store where my favorite four girls worked. I would chat with them, sometimes flirt, and frequently help them with their customers, thus leading to more work. I came to look forward to any time I could possibly get to stay around them. When they clocked out, we would often go out to the on-site bar and have several drinks. It was as close as I got to dating.
One quiet Sunday, when it was too rough to go out that day, I was hanging around as usual. Michelle, the tall blonde girl of the group, was complaining about her sleeping arrangements at home that weekend and how her neck hurt. “I don’t know if I can stand up for another two hours, my neck is killing me!”
I perked up and responded, “I’m pretty good with my hands. You want me to try to work out the kinks?”
Without hesitation, she took me up on it. “Please. I definitely need 'something'.”
I pushed the swinging door and moved behind the counter. As she was four inches taller than I was, I motioned for her to sit at the one stool behind the counter, and I slid into the small space behind it. I brushed her curly golden locks to one side and placed my hands firmly on either side of her neck, allowing them to acclimatize to her body temperature. As it turned out, my hands were warmer than her own skin anyway. Within seconds, I could feel her lean back and release into my touch. I worked from the hairline of her neck down only to the top of her shoulders, dipping slightly below her collar along her spine. That firm pressure along her spine gained the most response. I had her lean forward and worked between her shoulder blades and up to her neck, releasing the tension as I went. She asked me to go lower, but I complained that her bra strap got in the way of the smooth, even motion I felt worked best. She reached behind her back and snapped her bra free in one instant, smooth motion as her compadres laughed.
The first few minutes were definitely focused on the tension, but as her muscles relaxed, she started to direct my efforts by shifting her body to guide me to what felt best. After about fifteen minutes, it became obvious that this was no longer about her neck. The moans and quiet groans told anyone within earshot that she was in “pleasure mode”.
We were interrupted by one of the marina owners walking in the front door. He looked over at me behind the counter, the three girls chuckling, and the fourth girl moaning with her bra lying on the floor under her stool. “Um. I don’t know what’s going on here, but, no.” He wasn’t angry; in fact, he was laughing, but the massage was over. I excused myself and pushed through the swinging door to the other side of the counter.
Michelle gathered herself, picked up her bra, and pushed through the swinging door, paused to half-hug by reaching across my back and squeezing my shoulder toward her, then kissed me on the head. “Thank you so much. Ya know… you have awesome hands. Maybe I can buy you a drink later, and you could finish what you started?”
I’m sure I blushed. I wasn’t exactly sure what she meant, and the comments from her friends only confused me more.
It turned out she meant exactly what she said. No more, no less. Because of the windy weather and passing showers, the store was slow, and the owner came out of his office early and told the girls, “You might as well close out early and go home. No use you all standing here doing nothing.” So, almost an hour earlier than scheduled, the store was closed, and we moved our gathering to the covered bar area outside, which was also very quiet. The five of us lined up at the bar and filled the remaining barstools, more than doubling the number of patrons in one swoop.
Michelle spoke first: “He gets whatever he wants, on me Karen.”
The bartender turned to me. “Capt Morgan and Pineapple?”
I didn’t even have time to answer, and she was pouring my drink. A strong pour at that. The girls then all placed their own orders.
As soon as the drinks were put in front of them, Michelle reached behind her back, unsnapped her bra, and cleared her throat emphatically, “Ahemmm!” That was my cue.
I promptly resumed where I left off earlier, and for the next thirty minutes, I wasn’t allowed to lift my hands off her back except to sip my drink. She would hang her head low, her hair falling over her head to the surface of the bar, moan and groan quietly, absorbing my touch, then lift up and sip her drink, then lower her head again. All the while, the other three girls and I continued chatting as if nothing else were happening.
After about half an hour, she lifted her head up with a sleepy smile and grabbed and held my hand gently. “I needed that so much! Thank you.” Then she guided my hand off her shoulder and turned ninety degrees on her stool, signaling that I was no longer expected to continue. I slid into the chair next to her, and as I motioned for the bartender, I heard Camille’s voice. “Ummm. What do you think you’re doing? You may be done with Michelle, but I’m next.” With that, she put her money on the bar, waved her hand to the bartender to signal that my next drink was on her, then spun her stool enough to show me her back. She reached her right hand behind her, grabbed a handful of hair, then with her left, artfully pulled a hairband out and wrapped it around an instant ponytail, pulling the hair over her shoulder.
“Well… don’t just stand there, get started,” she ordered.
She was the most beautiful of the group, but she was the only one of the group who had a boyfriend, so I never envisioned being able to touch her, never mind run my hands all over her body. As soon as I had my drink and took a quick slug, I put my hands on her neck, as I did with Michelle. Camille spoke up.
“Oops, almost forgot. Don’t want this getting in the way.” She reached behind her, then unexpectedly raised her shirt almost above her shoulder blades. “Would you mind?”
I couldn’t believe this gorgeous, untouchable specimen of a woman was now asking me to undo her bra. RIGHT THERE IN FRONT OF EVERYONE IN THE BAR!
I complied obediently and separated the catch from itself, allowing the elastic to pull itself to her front. Seeing the red marks on her back, I quickly moved my hand in place of her bra and worked the pads of my fingers over the dented and pinched flesh.
“Oh yea, that’s nice. Thank you so much!” And she reluctantly let her shirt slide back down.
Then I was back to work. Camille was fun to massage. She was very responsive to touch and melted into the kneading and working of her muscles. If it wasn’t for the loud music, she would have made a spectacle of herself. Her friends ignored her moans as if it were normal, but I couldn’t help but feel a warmth between my own legs. Unlike Michelle, she wasn’t happy if I stopped for a drink and implored her friends to assist by feeding my drink to me, so my hands wouldn’t stop. She claimed it was because the condensation on the glass made my hands cold and that was “ruining her vibe”.
It soon became obvious that I had a new role. Rosalie slid close to Camille and made a point for all to see her remove her own bra. Insinuating that it was now her turn. Camille complained and insisted my service was not complete yet, and Rosalie pouted. Five minutes later, I was permitted to slide over and start on the new girl.
Rosalie’s muscles were firm and actually a pleasure to massage. I could feel the flesh react to my touch, as if it were alive itself. She begged for firmer touch, and I did my best. She too moaned and groaned, but hers sounded a little less sexual and more physically enjoyable. It didn’t stop my erection, though. Less “creamy” than Camille’s skin, Rosalie had a natural moistness to her skin, almost oily. It helped my hands slide more smoothly and invited me to maintain direct contact. So, unlike the other two, I mainly kept my hands under her shirt, albeit non-sexually. I think I enjoyed it as much as she did.
To end the night, I slid over to Cindy, who actually seemed less comfortable with being touched. At least in the beginning. Her stiffness seemed more self-induced by being touched in public than from being physically tense. She was the shortest of the group. Slightly heavy for her height, with short, smooth hair, and a round face. One would say she was the least attractive but still very cute. She was receptive to work around her neck but tensed if my hands slid lower. She also left her bra in place.
My strong fingers were growing a bit weary, so I was moving more slowly and gently, and that turned out to be her weakness. As I glided across her upper back and paused to slide my fingers on each side of her spine up and down her neck down to her bra strap, Cindy began to moan, “Oooooh…yeahhhh.”
I spoke quietly, “If you want me to go lower, I will need the strap out of the way.”
Immediately, she reached back and popped the strap, leaving the bra in place, but loose. She really liked the feel of my fingers sliding along her spine and guided me to keep my focus there. After a little while, she even shifted her butt in her seat such that she could push her shorts down her waist and directed me to turn my hands upside down, allowing my fingers even lower access. Standing behind her in the dim light, I could now see the crack of her ass, which meant my fingers were well down onto her butt. Each push below her waistband was met with a giggle, but the way she arched her back told me it was pleasurable. As my hands slid up her back, I would hear a negative-sounding groan, the pitch changing as they returned to the lower half. I would later learn that, although she was a bit embarrassed to be touched in public, she was the most sexual of the group.
The evening ended uneventfully, but I had spent two hours with my hands all over four beautiful women. I may not have “scored,” but I earned a new position in the group. After that night, any time I was around the girls, at least one of them wanted a back rub, or neck rub. The scene at the bar was recreated on several occasions as well, even including the barmaid on one or two of those occasions. The girls would openly talk about how they “loved having [my] hands on their bodies”.
I guess they were probably hinting to me, and trying to encourage me to “make a move”. But I was a natural-born chicken, and as much as I enjoyed my role, I was afraid to risk my relationships by trying a move on one or the other. As sexually frustrated as it made me, I was waiting for some kind of sign to help me figure out with which girl I had an actual chance. I settled into the role of “everybody’s friend and confidant”.
One afternoon in Late July, Camille had taken a weekend off to spend with her boyfriend, who was visiting. She had been driving Rosalie to work all week while her car was being repaired. Michelle and Cindy were headed to a party after work, and that left Rosalie scrambling for a ride home. It didn’t take much to twist my arm, and I volunteered my services. She offered to buy me a few drinks, and when the store closed, we slid over to the bar. We had one drink, but I had skipped lunch, so I talked her into keeping it light tonight so I could get some food. I offered to take her with me to get some pizza at the one pizza place in town.
We laughed and joked over dinner and had a rare couple of hours alone together. I had an early workday the next morning, so in the last light of the summer evening, I drove her back to her home. Her parents owned a fairly large summer house on the beach on the north side of the island, but I had never been there before. As I parked my little imported manual-transmission station wagon in the semicircle driveway by the front door, we continued talking and laughing. An hour passed, and we were still laughing and enjoying our time. It started getting dark, and I finally indicated I needed to wrap things up and get home.
Rosalie pouted, but acquiesced. “Oh kayyy,” she said reluctantly. With that, she leaned across the stick shift, and I met her in the middle, and she gave me a hug in thanks for the ride. I returned the hug enthusiastically, firmly meshing our upper bodies together. What happened next caught me (and seemingly her) completely off guard.
Our hug sustained probably a little longer than expected, and as we separated, she said, “You give such good hugs… I really wish I could sleep with you.”
My eyes grew wide, and my mouth went dry. I had only had sex one (unfortunate) time in my life, and a beautiful girl I really liked had just told me she wanted to sleep with me!
Rosalie froze when she saw my reaction. She laughed uncomfortably. “Um. That came out wrong… I think. I meant you’re like a stuffed animal I just want to lay with and hug and fall asleep with.”
That wasn’t any better. I too, laughed uncomfortably, but while she might have known exactly what and how she meant to say it, I still could only hear the part where she said she wanted to sleep with me. If the extended hug hadn’t done enough, her comment led to an immediate erection. Given the position I was sitting in the small car, there was no way to hide it.
As her eyes darted around looking for a way to get out of the situation, I think she noticed my little friend. I saw a smirk on her face, which I credited to the awkward comment, but would later learn was about my erection. She shifted away from the middle of the car and grabbed the door handle. “You know what I mean, right?”
Again, I only heard what I heard. Her question seemed like she was pushing that point. So I turned off the car and grabbed my door handle. Her head tilted like a confused puppy, then she smiled and got out of the car. She paused as she held the door open and waited to see what I did. I got out, too. She turned toward the front door and readied her key. I was beside her in a few seconds.
We entered the house into a large open living room. While this house was large, it wasn’t luxurious, but it was tastefully decorated and spoke of her family as more wealthy than I had realized. I got a quick tour of the main floor and upstairs, then we paused in the open section between the dining room and living room. I was following her like a puppy, very unsure of what I was supposed to do next, and she looked at me. Then, without warning, she asked, “Do you kiss as good as you hug?” And she squared up in front of me. I closed my eyes and leaned in. Her lips were full and moist, and her tongue was more active than any girl I had kissed. I responded as best I could and pulled her close, my right hand on her lower back, pulling her to me as I pushed my groin into her thigh. I may not have had sex but once, but I felt good about my kissing and petting. I’ve been told I’m good at it and, by the way she melted in my arms, I took it to mean I passed her test.
“Okay then. Now that that’s out of the way do you want to finish the tour?” I wasn’t exactly sure what she meant, but followed her again. We continued through the house to the one room we had not visited, her parents’ bedroom. It was a fairly large bedroom with a king-size, four-post bed, with an area rug over a hardwood floor. By the pillows sat two large stuffed animals, a white bear with a plaid tie and a fluffy golden dog. She walked over to the bed and turned them to face the wall.
My blood was pumping, and that last act set off my erection again (it was already growing from the kiss). She sat on the foot of the bed and patted the mattress beside her. I obeyed. As I sat, she immediately turned and started kissing me. In seconds, her hand was plopped on top of my erection, pushing down firmly. Her kisses were aggressive and passionate, her tongue digging between my lips and wrestling with my own. I kept my hands on her shoulders and lower back, not sure exactly how to proceed, just waiting for cues.
We kissed for several minutes, the heat rising between us. Then, all of a sudden, she broke off and stood up. I was confused, but still following any instruction she gave.
“We have one last room to show you.” And she backed away and turned around. I rose and followed her into the bathroom. “This is my favorite bathroom ever."
The doorway opened into a very large bathroom, almost bigger than the bedroom of my apartment. There was an entire wall to the left that encompassed two full sinks separated by a large make-up mirror on a swinging arm. There was a leather-cushioned, ladder-back chair tucked into the gap in the cabinets under that section of countertop. The back wall had a small lounge chair, and the toilet sat oddly out in the open near the corner. To the right was a very large recessed shower area. There were dual rainshower heads, perched six feet up the wall, and a small window to either side of the shower heads, but slightly higher. Along the wall, next to the doorway, was an exposed linen closet with a sliding linen curtain hanging over the front. The recessed area of the shower floor could have doubled as a dance floor; it was so large. There was no door or curtains for the shower. It was wide open.
Rosalie turned and kissed me again. “I don’t know about you, but I need a shower. Care to join?” Without waiting for my answer, she crossed her arms in front of her and flipped her shirt over her head in one motion, flinging it to the floor near the hamper at the far end of the counter. She kicked her socks off almost as adeptly and dropped her shorts before I finally accepted the fact of what was about to happen.
I had seen boobs before. I had seen a few asses, but the one time I had intercourse, that girl insisted on lights off. Seconds later, in the full light of the bathroom, Rosalie was standing naked, staring at me and wondering what was taking me so long. I had realized nobody had ever seen me completely naked, either. I became self-conscious that I may not measure up either in physical size or ability to perform. I stood momentarily with my tighty-whitey underwear struggling to conceal my erection.
Sensing my apprehension, Rosalie stepped into the recessed floor area to the side of the showerheads and turned them on. I used the opportunity to turn my body and kick off my underwear. In my feeble logic, my penis would look larger from a side view, and by waiting for her to turn away, I could have a little control over what and when she saw me.
She didn’t seem to mind. When she turned to me, she walked right at me and never looked down. Her dark brown eyes cut into me, and I turned to meet her at the edge of the shower step. She grabbed my penis without ever looking at it and locked lips with me. I looked down at her “D+” cupped breasts standing proudly and glaringly white against the deep bronzed tan of her belly and shoulders. She tugged slightly on me as we kissed. Her tongue was frantic now, her face mashed into mine, and I was clearly overmatched by her experience and confidence. I was afraid I would lose it too quickly, so I gently pushed her towards the running water, and we continued our kiss under the flowing streams of warm water.
She liked the idea and parted from me long enough to grab a bar of soap, vowing to “clean you like you’ve never been cleaned.” And she was right. Short of when my mother bathed me as an infant, nobody had ever soaped me down. I can’t say it was the cleanest I have ever been because most of the soaping was around my penis and ass. She ran her soapy hands up and down my chest a little and along my back, but continuously returned like a magnet to the steel of my erection. She seemed to know how far to push it before backing off (of which I was extremely grateful), and, when she thought I was too close to losing it, she stepped back and handed me the bar of Dove.
She stood beneath the cascade, and I knelt in front of her, starting at the bottom of her feet. I worked my way up. I was determined not to miss a single inch of her body and see it all as close as I could. I parted her cheeks and slid the bar between her firm buns. I lowered the soap and used my other hand to spread the soap more. My free hand moved around the front and pulled soap from between her legs to lather the hair of her fully grown bush. I had never seen a pussy in the light before and had only “dipped a finger” here or there. On my knees now, I was up close and personal with one and could see all the parts I only knew from porn mags. I recognized her clitoris as that bright red swollen nub I had only imagined. My soapy finger slid over that nub, and she quivered and gasped. I slid my finger up and down the slit, attending to her swollen nub, and she started pushing it against my hand.
As I looked up for her reactions, I saw her eyes closed and her teeth lightly clenched on her lower lip. Her breasts were glistening with moisture, and I couldn’t wait any longer to get a feel of them. Staying on my knees, I ran both hands up from her thighs along the curves of her stomach and onto those pearly mounds I had only dreamt about. They felt even better than they looked. Her dark nipples stood out proudly, and her body reacted almost as much as her clit as I washed them. I turned her to allow them to rinse, then rose to place my lips over them and suck those happy nipples. Her head tilted back, and her hands grabbed the back of my head. A few seconds later, her hands guided me back down to her pussy, now also free of soap. I darted my novice tongue between her swollen lips. I grabbed the nub of clit between my tongue and my upper teeth and pressed gently but firmly.
Her hands pushed my head against her forcefully. I could barely breathe as I sucked her clit on and off in rapid succession. Her knees started to bend, and her hips thrust into me while her hands trapped me in place. She started to shudder slightly, then grabbed my hair and tilted my head back and looked in my eyes. I read her expression as if to say “Shower is over”.
I stood up and kissed her again, and she reached for the wall controls. The one drawback of the open shower hit me suddenly as the warm water stopped and the cool, air-conditioned air hit our bodies. She hopped quickly from the shower to the linen shelves and pulled two plush white towels, handing one to me and starting to dry herself with the other. She wrapped her towel around her, covering her boobs and barely covering her crotch, then hugged me close, grabbing two handfuls of buns in the process. My erection poked its head up under her towel as we kissed, and I could feel the coarseness of her pubic hair.
She stepped back from our kiss, turned away from me while grabbing hold of my penis, and led me back into the bedroom. She stopped at the foot of the bed and knelt on the floor. As she kissed the head and shaft of my penis, it jerked with each touch. As she put her mouth over it and slid on and off it a few times, I could feel the urge coming already, and I placed my hand on her chin, tilting it up to look at me. I had no intention of losing control quickly and risking a premature end to our encounter.
I gently lifted against her chin, and she rose. My hands moved to her shoulders and I very gently nudged her backwards until she felt the edge of the bed and sat. It was my turn to hit the floor, and I was on my knees, inches from her pussy, and I watched the smile on her face as she leaned back on her elbows and scooched her butt a little higher on the bed. My hands separated the towel, opening her to my view as I dove in for my first real taste of a woman. I covered her entire gash with my open mouth, breathing warm air onto and into her crotch. Her head tilted back, her wet hair hanging onto the blanket. My tongue searched for and found its mark. Like before, I trapped the nub between my lips and teeth, but now I had more control. From this angle, I could also penetrate her vagina, so I plunged my tongue as deeply as possible. Each thrust resulted in a counter thrust from her hips. Back and forth I went, from the hole to the nub, playing each action until she would react.
Then she took control.
As I was working on her nub, she grabbed hold of my head and thrust her hips against me, trapping my mouth in place. She ground her hips side to side and back and forth as I increased my pace against her clit. Her moans turned to grunts, and her eyes rolled partway up in her head, her tongue pinched between her own teeth and lips. As my pace increased, so did hers, and it became a race. Then it happened. Her knees tucked up toward her chest, her breathing stopped, and she grunted. It was a long grunt of release as she came so forcefully, I got a little scared. I had never seen a woman orgasm, but this was clearly what was happening. Her face grimaced in what looked like pain, but her actions screamed pleasure. Her hands jammed my face so firmly into her pussy that I could no longer move my tongue (which was apparently the point). For a good ten seconds, I couldn’t even breathe.
Then, with a forceful gust of breath and a subsequent groan, she released my head enough that I could breathe. I automatically started fluttering my tongue on its mark, and seconds later, she convulsed again, mashing my face in place so hard I couldn’t move. I was mesmerized. I kept repeating my actions until she eventually forced her hand between my face and her crotch and panted frantically in exhaustion. Next, she grabbed my chin and guided me up on top of her.
I was now standing, leaning over her on the bed as we kissed. I felt her hand grab hold of my erection and aim it towards the prize. She was so warm and wet, I slid in effortlessly. It felt so good, I didn’t want to move. I held it in place, and she tried to wriggle beneath me, but she couldn’t gain the leverage to thrust. I lay there on top of her, afraid to move for what seemed like an entire minute.
Then I very slowly started to thrust. I had now been erect for more than half an hour and surprisingly, that worked in my favor. For some reason, the urge to come, which had seemed so close a few minutes ago, relaxed, and I took advantage of that fact. I directed her to slide up higher on the bed and matched her movements until only our feet dangled over the end. She pressed into me hard and signaled a desire to thrust against me. I matched her, thrust for thrust, and in moments she was starting to grimace again as her pace quickened. Then she pulled her knees up and gave a grunt as she reached another orgasm, shuddering and biting onto my shoulder so hard I thought there would be blood. She grabbed my ass and pulled me so firmly that I couldn’t move.
I started to feel it building. Suddenly, I panicked. Realizing I had not put on a condom and mashed into her like I was, I risked coming deep inside of her. I yanked myself out of her, and seconds later, a stream of white goo emptied out into her belly button in waves.
“Awe. What’d you do THAT for?” She spoke with disappointment.
“I didn’t have a condom. I didn’t want to take a chance.”
“But that’s my favorite part! Besides, I’m on the pill. You have nothing to worry about.”
While I was relieved to hear that, I was also disappointed that I hadn’t thought to deal with that before getting into this spot. She relieved my fears when she grabbed my ass again and pushed me down onto her belly, smearing all the little tadpoles everywhere. Then she kissed me deeply. This was not the aggressive tongue lashing of earlier kisses, but a deep, warm, firm kiss of appreciation.
She giggled. “You know, I honestly didn’t mean this when I said I wanted to sleep with you. I really meant I just wanted to sleep with you!”
I just shrugged sheepishly.
The come had begun to ooze down her side but was caught by the towel. We decided to get up and go back to the shower and wash off. This time, we each soaped ourselves, but it didn’t matter; my erection returned to all its glory.
As we dried ourselves once again, she grabbed hold of my erection and said, “I was going to ask if you would actually want to sleep here with me tonight (Is that better?), but I have a feeling we wouldn’t get much sleep.”
“Yeah. I have a feeling that might not be the best idea. I have to get up for work in about four hours. I think I had better call it a night.”
I reached for my underwear and shorts on the bathroom floor, and she stood in front of me naked as I dressed. “I think we should keep this our ‘secret’ for now, ya know?” She went on about not wanting to complicate things at the store and how she hadn’t really thought about having a boyfriend with just a month or so left in the summer.
We agreed to “keep it cool,” but that didn’t really work out very well because every time there was even a chance of being alone, we ended up back at her house. It made for a great summer for me… no strings sex whenever I (or more correctly, she) wanted it, and it all came about without the usual discomfort and torture of me trying figure out how to play the game.
