Strangers on a Train part 3: Restaurant Shennanigans and a Bit of Backstory

Part 3

I woke up to the warm pressure of Sofia’s supple skin pressed against my naked body. Did last night really happen? How could this woman be real? It seemed to good to be true.

But, it was true, every glorious moment of it. I lay in bed lingering for a moment, taking in Sofia’s scent, nose nuzzled against her graceful neck. The improbable geometry of her body, the physical manifestation of quadratic functions, created a topographic map comprised of rolling hills and valleys beneath the satin bed sheets. I gently propped myself up, trying not to disturb her sleep, letting the vision of her slumbering form sink in.

Sofia had been pressed against me sleeping on her side, but when I sat up, I created a small space between us allowing her to roll onto her back. The movement caused the sheets to slip away, exposing her breasts, which crested and fell with every deep breath. Again, I stopped and watched the hypnotic undulations, a smile creeping across my face. Ever so gently, so not to wake her, I pulled the sheets further and further down her body, the smooth fabric gliding along her skin, each bit of exposed flesh more enticing than the last.

There she lay, naked and perfect, one knee bent, the other extending straight out offering a glimpse of her beautiful pussy, which mere hours ago was so tightly wrapped against my hard cock. Even asleep, her body begged for attention. Gingerly, I nudged apart her legs, allowing me a clearer view of her most intimate parts. Her inner lips protruded slightly from between her smooth outer labia and as I eased her legs wider they began to separate providing a flash of pink, which stood out nicely against her otherwise caramel skin.

I positioned myself in the space I had cleared between her two tan limbs, my head inches from her sex. Her delicate scent invaded my nostrils, the faint smell of sweat mixed with a sweet tangy feminine musk. I carefully placed my mouth over her vulva, tasting her, my tongue lightly pressed between her innermost folds.

Sofia, stirred and groaned, a smile gracing her lips, but remained asleep. Gradually, I pushed into her opening allowing her honey to coat my tongue. I lapped lightly, dipping my tongue in and out of her syrupy hole, as her perfectly manicured pubic hair tickled my nose.

I began to lose myself in the task at hand, working my skilled tongue, coaxing out her sweet molasses. So lost in my mission, I failed to notice her draw her knees up around me on either side of my head.

“Mmmmmm…. Good morning, lover,” she murmured sleepily as her fingers rummaged through my messy morning hair causing me to pause, look up, and grin.

“Don’t stop, silly,” she teased. “Get back to work…. That’s it…. Mmmmm…. Yes, sí, just like that,” my tongue once again greedily drinking her in. My hands wrapped around her thighs enjoying the feel of her smooth skin against my hands. I reached one hand around further and with my middle and index fingers, pulled back on the skin at the base of her pubic hair, retracting her hood, and fully exposing her pearl. I painted her pussy with kisses all over, coming painfully close, but avoiding her little button with each passage, keeping up my mischievous motions until she couldn’t take it any longer.

“Don’t tease me,” she begged as I released a devilish stream of air from my pursed lips directly onto her uncovered clit. She fidgeted in the bed trying to push her sex against my practiced mouth again.

Finally, I gave in to her needs. My lips closed around her and my tongue pressed on her magic button. Her hands pulled my head in as she arched her back, bucking against my face. All the teasing had left her burning with anticipation, and so when I finally did make contact, she started to cum instantly holding my head tightly against her. My lips stayed glued to her as her body jerked and flailed, tongue swirling, as wave after wave crashed over her body in one long continuous orgasm.

Several minutes passed before Sofia’s hands became unclenched, relinquishing my head from her strong grasp allowing me to pull away from the quivering, wet mess between her legs. Her body continued to spasm and tremble in small aftershocks as I raised my head up, face shiny with the evidence of her climax. Smiles across both of our faces, content with the morning’s fun, I laid my head on her lower abdomen, cheek pressed against her skin, pubic hair right below my chin. She stroked my hair as we just lay there fulfilled for the time being.

—–

The late Saturday morning summer sun came careening through the large industrial bedroom window, casting a grid of shadows over the white sheets and our naked bodies.

“So, beautiful,” I began, resigning to the fact that a new day was upon us, signifying that the magical night, which we had already let slip into morning, was finally truly over. Pealing my face off of her bare abdomen and sitting up: “What are we going to do today?”

A smile spread across Sofia’s lips. “You mean you want to spend the day with me? It’s not too much?”

“Too much of what?” I probed intoning that my lack of comprehension was a result of the absurdity of her question. “Last night was… well, amazing… in so many ways. I really had an incredible time with you. Of course I’d love to spend the day with you.”

“Oh good,” she replied in her sultry Catalan rasp. “I was afraid last night was going to be a, what do you call it? One night stand? Well, I need to go home and change my clothes. Besides that…. Hmmm, let me—“

“I have a better idea” I interjected. “The sun is shining and its Saturday. Let’s go grab some brunch first, maybe take a walk along the water, and then call you an Uber back to your place a bit later. I’m sure your clothes from yesterday are dry by now. And besides,” I added with a wink and a smile. “We already washed up last night before we went to sleep, remember?”

Once dressed and freshened up, we left the apartment and headed out to greet the world. The warm sun had erased all the traces of yesterday’s deluge save for the faint olfactory hue of damp grass that lingered in the thick mid-July air. Arm in arm, we circled the corner and shuffled past the throng of tourists outside Grimaldi’s waiting for their taste of brick-oven bliss, reminding me of a time before everyone was a foodie and you didn’t have to wait three hours for a pie. But, that was a long time ago, long before tourists flocked to the revitalized Brooklyn waterfront and long before I moved into my loft. “I guess this is what progress looks like and I’m both a victim and a contributor”, I thought to myself.

We continued down Front St. to the River Café. I wanted to impress Sofia and although severely underdressed, I decided that the tasting menu brunch and the skyline views were too good to pass up. And, in all honesty, I really wanted to impress Sofia. Besides, I was a bit of a regular there, entertaining out of town accounts frequently and as a result, I had become friendly with the Miatre De.

We turned down the old cobblestone driveway leading to the impressive and somewhat hidden entrance. We ambled past the ambient array of lanterns and unusual miniature forest plants, which aided in the illusion of the fairy-tale setting. As we approached the door, the tuxedoed doormen began to gesture, most likely to deny us entry due to my lack of sport coat, when they were interrupted:

“Mr. Davidson!” greeted Alec, the Maitre De in the overly effusive tone stereotypical of men of his position. “So good to see you! Please, come right in!”

We walked through the large, wooden doors and entered the dining room The iconic restaurant had been destroyed during Sandy a few years back and the owner, Mr. O’Keefe had taken extra care to pay for a painstakingly detailed, museum-quality restoration complete with the dark wooden bar, wicker stools, white table cloths, and of course, a house pianist gently tickling the ivories of a grand Steinway.

“Where did you take me?” Sofia whispered as she took in the scene. “This is much too fancy. I’m not dressed for this.”

“Don’t worry about it,” I leaned in and whispered back. “You look beautiful. We’ll be fine. I come here all the time.”

“Right this way,” injected Alec. “Mr. Davidson, I hope you don’t mind having a seat at the bar, I should have a table ready for you in 20 minutes.”

We perched ourselves on the tall wicker stools along the bar and ordered cocktails from the white jacket clad bar tender—a Bloody Mary for me and a Mimosa for Sofia. We sipped our drinks, the alcohol lubricating our conversation and Sofia gradually became more comfortable sitting in the impressive room. The first round went down fairly quickly and we still had several minutes before we were to be seated. And, although I didn’t really want to leave Sofia’s presence I decided it was better to excuse myself to the bathroom now then to wait until we sat down.

I walked down the hall to the large old men’s room, pushed passed the heavy frosted glass door, and entered one of the two private stalls. Just as I unzipped I heard the bathroom door open followed by what sounded to be the click of the lock. Then, the unmistakable sound of high-heeled shoes tapping against the tile floor, each step bouncing off the walls. By the time Sofia rapped her fingernails against the stall door, I had already started to swell with anticipation for what I knew was coming.

I opened the door, literally standing there, dick in hand. Sofia slipped inside, shut the door, and immediately dropped to her knees. Without hesitation, she engulfed my semi hard member, swallowing it to the hilt, rolling it around on her tongue, causing it to inflate until she pulled away to catch her breath. My cock, glossy with her saliva now stood firm, bobbing in front of me through the fly of my pants.

“Hi baby,” my cock inches from here face, her two hands both sliding up and down the length, twisting over the sensitive head. “I got bored. I hope you don’t mind,” she added with a devilish grin.

“Of course I…uhhhhh…fuck… that feels good….” But, before I could even finish the thought, her warm mouth was closing around my head again. Her enthusiastic hands continued to work my slobbery shaft as if she was trying to wring out my precum, her head bobbing and tongue swirling over the helmet, eagerly lapping up whatever she managed to squeeze free. I braced myself, hands planted against the stall walls on either side and watched as this godsend greedily devoured my manhood.

“Quick,” panted Sofia as she pulled her head off of my shimmering cock, a sticky mixture of precum and saliva dangling in one long tendril towards the white tiled floor. “Sit down. I want to ride you,” she commanded as she pulled down my pants and boxer briefs in one swift motion.

The cold porcelain of the closed toilet seat sent a quick shock of surprise up my spine as it made contact with my bare bottom. I stroked my cock, still saturated in Sofia’s saliva as I watched her quickly turn away from me, bend over, and slide her leggings down over her rubenesque backside, a hint of moisture visible on her puffy pussy lips. In one, swift motion, Sofia’s hand wrapped around my stone pillar, guiding it between her slick, hungry lips, lowering herself down and letting her warmth envelop me. Her inner walls contracted, the smooth flesh greedily grasping every solid inch.

She placed her hands on my knees, which were spread apart as she closed her legs tight enhancing her Kegel vice-grip. Using her hands for leverage she began to bounce her bountiful backside up and down, stopping every few strokes to grind her clit against me maintaining a steady, but aggressive rhythm. I sank my fingers into the soft flesh of her hips, moving my arms with her in perfect sync, assisting in her frantic, vacillating motions.

Within moments I could feel Sofia start to tense up. She pushed down hard against me, grinding her pussy, her escaped juices lubricating her movements on my lap. I reached up covering her mouth with my hand to stifle her screams as her orgasm overtook her, my cock still buried to the hilt inside her hot, wet, constricting pussy.

Sofia’s intense grip brought me right to the edge and I could feel the sticky white fluid boiling up inside. I clenched hard, holding back the inevitable eruption, letting Sofia come down from the dizzying heights of her powerful climax. Before she could even catch her breath she was on her knees between my legs, causing me to exchange one wet orifice for another. She swallowed my cock whole, my head passing from her mouth into her throat and, as she pulled up slightly, my cock twitched, spraying my cum to the back of her throat. Sofia’s lips sealed tight around me and she swallowed repeatedly, making sure to not let a single drop escape.

She let my softening cock slip from her lips and looked up at me with a wicked grin. Then, licking her lips she giggled, “So, let’s get some lunch.”

—–

We straightened up and discretely slinked out of the bathroom returning to the bar just in time for Alec to walk up and tell us that our table was ready. We followed him through the restaurant, weaving between white-cloth tables doing or best to contain our guilty smirks. Alec stopped in front of an empty table in the far corner against the wall of windows and pulled out a chair for Sofia.

“Madame,” he offered.

We took or seats and I noticed Sofia staring out the window at the impressive view of the Brooklyn Bridge spanning the East River, a brown stone rainbow arching over the water, separating the outer borough from the majestic Manhattan skyline. Skyscrapers reached impossibly high in the Summer sky, their points forming the EKG line that measures the city’s heartbeat.

“It’s so big. I don’t know if I can ever get used to living here.”

“But Barcelona is a big city too, isn’t it?”

“Yes, but not like this. Barcelona is old with narrow streets that have been there for hundreds of years. The city can feel endless, but it has a charm. New York is just so imposing. The giant glass buildings…. All the people… Everybody always going somewhere. It’s non-stop motion. It’s not the same.”

“Barcelona isn’t like that?”

“No. In my city we take a sietsta. Being well rested, having fun, enjoying life… that is what Barcelona is. New York is chaos.”

“Well, I guess I’m used to it. It’s what I know. I mean I grew up here.”

Over the three-course brunch, I began to tell my story to Sofia. I told her what life was growing up, my interests, about school, and even a bit about my sexual experiences. Sofia listened intently while slurping down oysters and enjoying pancakes with gold-dusted milk chocolate.

—-

To say my upbringing was different than Sofia’s would be a massive understatement. Whereas she was expected to live a religious and studious life, forced to ignore her creative tendencies, I, on the other hand was encouraged to pursue my passions, explore ideas, and experience as much as I could. The product of a liberal, academic, Jewish New York family, everything was always up to debate and interpretation. Learning to negotiate wasn’t just a nurtured skill, but a way to tackle life. Anything I wanted to do, I could.

As a result, I spent most of my youth chasing one creative pursuit or another. From painting, to music, to theater, my family encouraged it all. If had a performance, I could count on them to be there. If a painted something, they would have it framed. Perhaps at times I was a bit of an underachiever, an idea that was reinforced by the results to my direct actions. Whenever I became interested in something, I became fully engrossed and would excel on an extremely high level. Conversely, If I was uninterested in as subject, I would merely skate by. Although never becoming a master of one specific field, through practice and positive reinforcement, I became quite adept in almost everything I deemed worth an effort.

There was however, a downside to my scattered interests. Throughout school, I never quite fit in with any one social circle. I prided myself on being more talented than the music and theater geeks and more importantly, too cool and “normal” to actually hang out with them on a regular basis. It was the same thing with the athletes. Although I was interested in and fairly good at several sports, able to hit three-point shots and rattle off useless statistics memorized from the Post’s back pages or parroting Sportscenter anchors, I never really clicked with jock culture or the team mentality.

Ultimately, I wound up spending most of my time at school mingling with the popular kids, curbing my more eccentric proclivities and interests in order to fit in with their vapid click. They were nice to me, never putting me down or outright discluding me, but on the other hand never fully including me either. Lunch hours were spent listening to useless gossip and inane banter typical of teenagers everywhere. I feigned interest and contributed enough, but remained somewhat disconnected and removed.

The reservedness in which I dipped my foot into the varied social pools had its effect on my ability to make any headway with the opposite sex. For years I would pine for girls, all of whom resided in the upper strata of the social hierarchy, lusting after them, unable to understand why they would prefer to be with the bland, characterless teenage boys instead of me. I could offer them a balance of charm, intelligence, and good looks that these ubiquitous dullards could never match. On the other hand, I knew several girls, some of whom were fairly attractive, but who mostly existed in the more outlying social spheres who were quite interested in me. Their friends would tell me they liked me, encouraging me to ask so-and-so out, but I would never act. And, as a result, for most of my teenage years, any girl I finally worked up the nerve to ask out, rejected me, denying me my first kiss until I was much older than most of my contemporaries.

And, like most teenage boys, or so I thought, I was obsessed with sex. When I was 12, I discovered a stack of VHS tapes hidden in the back of my father’s liquor closet and I quickly became fanatical. As with anything I would take an interest in, the need to watch them, to observe them, began to drive my actions. I would hurry home from school on days when my siblings had sports practice just so I could have the house to myself, to study these tapes, and of course, to jerk off my teenage cock, which I had started to form a new relationship with. This continued throughout high school, watching the films, broadening my perspective on what was sexually acceptable, studying the techniques, and fantasizing about what it would be like to finally have the opportunity to reenact what I had seen with any number of the girls that I wished would notice me.

But, I never really got that opportunity—at least not the way I thought I would. I did however get the opportunity to spend a month in Berlin during my senior year, which looking back may have been the most important event of my young life. My school had been selected to participate in a program that sent top students overseas for part of a semester and although I didn’t qualify on grades alone, my vast and varied activities and interests pushed me into contention for one of the coveted slots. And, of course, my parents fully supported this.

“How could you not go?” they insisted. “These are the opportunities that separate you from the crowd.”

And truthfully, I didn’t disagree with them. I believed I was special and I deserved this opportunity and so, as with anything else I set my mind to, I made it happen. I aced interview after interview and wrote compelling essays highlighting my ability to think creatively on an unusually high level crafting a picture that went far beyond what my grades alone communicated. I demonstrated my interests in art, culture, literature, and the humanities—subjects that most teenage boys ignored or at best, of which they had rudimentary understandings. Never once did I question if I would be accepted, almost taking for granted that there was competition. I knew I was a perfect fit for the program, yet when the day came and I was finally accepted, I was still filled with joy and pride.

—-

I left for Berlin that spring, excited for what the world could offer. Upon arriving I discovered a vibrant city with flourishing art scene. Although I was only 17 at the time, people assumed I was an adult mostly due to the fact I was living in Europe without parents or any real responsibilities other than few classes I had to make sure to pass. I was able to attend concerts, art openings, and all means of cultural events that although existed in NY, I had never had access to. In Berlin I could be myself—free to be eclectic and inquisitive and explore the most erudite and artistic avenues my mind could wander down. Momentarily, I was free from the confines of my own pretensions or more accurately, rewarded for them.

To be cool in Berlin was to be avant-garde. People around me inspired me, shunning all forms of homogeny, and looking for uniqueness and ideas in everything they encountered. And, I certainly stood out as well. I was a novelty. Something new to them—an academically and artistically inclined New Yorker overseas for the first time. I relished the attention this position gave me and for the first time in my life felt understood and even lauded by my peers.

The only place in which I initially didn’t excel was with women. Years of rejection back home left me shy and unable to approach girls, especially those to whom I felt truly physically attracted. My typically fluid conversation skills would falter around beautiful girls, unable to sound natural when all I could think about was what it would feel like to kiss them, touch them, to be inside them. It was debilitating and exceptionally awkward for me considering, how confidant and at ease I seemed to all of my new friends.

Most nights I would return to my host family—a boy my age, Stefan, who was tasked with showing me around the school and his single mother, Helen—and relieve the pressure of the day’s interactions with the opposite sex by stroking myself before going to sleep. One night, about halfway into my stay, I quietly snuck back into the small flat my host family rented hidden on a side street in the Mitte section of the city. It was a convenient location regardless of where the night would take me. Even though I would frequently find myself out on the east side, attending shows in Kreuzberg, the flat was central and easy to return to at all hours of the night.

I carefully unlocked the front door, making sure to muffle the noise of the deadbolt click as I had done many times before. Then, after removing my shoes, I slinked through the dark apartment, stepping as lightly as I could and trying to avoid accidentally knocking into furniture as I headed towards my bedroom. I opened my door, which omitted a slight, but audible creak before stepping through the entrance, turning on the dim bedroom light, and offering a sigh of relief that once again I had made it back to bed without disturbing anyone.

I slipped out of my clothes, smelling of cigarettes and alcohol, a dank aromatic reminder of night’s fun, until I was left in nothing but my boxer shorts. I thought about the drinks, the conversations, and the loud punk band I had seen at SO36. But mostly, I thought about the beautiful blond girl, dressed in tight black, that had been dancing all night to the distorted music.

“Fuck,” I thought to myself as my hand slid into my boxer shorts. “Why didn’t I dance with her, buy her a drink, fucking talk to her—something?!?! Fuck she was hot.”

As on most nights, I slid my hand under my waistband and my young cock quickly started to grow as I massaged the increasingly firm flesh under my boxer shorts. I shuffled over to the small European twin bed in the corner of the room, sliding my last piece of clothing down my legs and stepping out of my boxers, leaving them on the floor. Now, lying back in bed, I began to slide one hand up and down my throbbing teenage cock, using the abundant precum to facilitate the motions.

“Mmmm…” I groaned, eyes closed, enjoying my touch, picturing the mystery girl from earlier that evening.

I started moving my hand faster and faster, up and down the rigid shaft—familiar gestures that I had practiced so often, my cock standing perpendicular to my supine body. Faster and faster—violently propelling my hand along the whole length with type of impatient enthusiasm typical of a teenager. I bit my lip, stifling a moan as I shot my load into the sky, the first several spurts landing on my chest and stomach before the last bit dribbled out the tip and down my length, eventually pooling by my balls.

I slowly opened my eyes, the room coming back into focus as the haze of my orgasm wore off and there she was. Helen, my host mother, was standing in the doorway; robe open, hand in her panties watching me.

“Oooohhh… that was so impressive,” her husky tone combined with her German accent as the sexy sounds escaped her lips. “I want you to do it again.”

I froze, hand grasping my still hard cock, unsure how to respond.

“Don’t be shy,” Helen encourraged, her 40-year-old, 5’8” womanly frame approaching the bed. “Here, maybe this would help.”

With that, Helen stepped fully out of her robe, and was left wearing nothing but her, damp white cotton panties. I soaked in the site of her body, in awe of her mature feminine curves. Her breasts were full and round with just enough sag to remind you that she was indeed a mother, capped with large pink nipples, which jutted out begging to be sucked. She was toned enough—not the body of a young athlete, rather the fit frame of a middle-aged mother who simply ate fairly well and walked regularly to get from place to place. She was soft in all the right places featuring a small slight paunch that comes with childbirth and wide matronly hips. This wasn’t one of the girls from my tapes or from class that I fantasized about. No, this was a real woman and for the first time in my life, a real woman was naked in front of me.

“That’s a good boy, stroke that dick for me….mmm that’s it… nice and slow…good…use your cum to help your hand slide…”

I followed her instructions, my teenage stamina allowing me to be rock hard again. Helen sat on the foot of the bed and I could sense her body’s presence. Her feminine sexuality placed and electric charge in the air and just having her near me sent a shiver up my spine. I slid my hand along my cum-slicked young cock in a slow steady rhythm eyes transfixed on Helen as she licked her lips, fingers moving inside her panties, whispering more instructions.

“yess… good… don’t speed up… control yourself… mmm… like that. Look how big and hard you are… is that for me?”

“Yes,” I managed to croak back, my voice fragile and nervous, my head meagerly nodding in case I wasn’t actually able to speak.

“Mmmmm… stroke it… I bet that feels so good, stroking your big dick, watching me, doesn’t it? I bet you want to put it inside me. You do, don’t you. I bet you want to see my pussy…”

“Ughhhh…mmm hmmm… yes please.”

“Be a man, my dear, tell me what you want. Don’t be afraid to ask.”

“I uhhh…” taciturn with a teenage awkwardness. “I uhhh… I want to see your pussy. Please, Helen, show me your pussy.”

Removing her hand from what I imagined was the very damp confines of her panties, Helen latched her thumbs around either side of the waistband, shimmied her hips and peeled the wet panties down her legs before dangling them towards me with an outstretched arm.

“Take them,” she commanded. “Smell them. Do you like that? Tell me what they smell like.”

I took her panties from her, the fabric warm and sticky with her juices, and brought them to my face. I inhaled her scent, a deep womanly bouquet of rose petals and copper, somehow familiar, but completely new.

“Mmm…” I nodded approvingly unable to put the words together to express what I was feeling. Then sheepishly: “They smell… ummmm… sweet…” my words trailing off both embarrassed and excited.

Helen had climbed up onto the bed fully and was sitting opposite me, knees drawn up offering a full view of her most hidden treasures. She was cupping her large breast with one hand while the index and middle finger of her other were buried in her wet opening down to the second knuckle. The tendons and muscles along the top of her hand visibly contracted and released as her fingers massaged her insides.

I had seen so many pussies in all the videos I had watched, some bald and tiny, others trimmed with puffy lips, but this was somehow different. Helens lips were meaty and full and protruded from the pelt of curly dirty blond hair that covered her swollen mound. The large lips clung to her fingers as they worked. My eyes mesmerized by her every movement still unable to fully comprehend the situation I was in.

“You do like it, don’t you? You dirty boy,” She teased and enquired, my cock twitching affirmatively as I continued to run my hand over the length at her prescribed rhythm. “Now two hands… yesss… just like that… slowly still…twist your wrists…mmmm… there you go…. Picture yourself sliding in and out of me.”

I followed her every word, stroking exactly as she commanded, using two hands, my shiny head poking out from my fist as my hands reached the bottom of every down stroke. Then, back up and over the tip, coating my palms with a fresh slick of precum each time.

“That’s it… faster now, still in control, not too fast. I don’t want you to cum until I tell you to.” Helen, now alternating between burying her fingers in her oozing honeypot and removing them to vigorously massage her large, extended clit groaned in approval at my ability to follow her instructions. “God your dick is so big and beautiful. It would feel so amazing inside me…mmmm…. fuck…. Yessss… I bet you make the girls your age go crazy.”

“I…. I… I’ve never been with a girl….” A look of embarrassment crept across my face as my hands slowed down.

“Come on… keep stroking… mmmm… that’s right…” I resumed the pace of my self-gratifying ministrations. “But surely when they see your big beautiful dick, they can’t resist. Look how marvelous it is.”

I stopped stroking all together. “No girl has seen it. No girl has touched it. I’ve never even kissed a girl,” my eyes now gazing downwards betraying what I hoped was an emotionally reticent response.

Now Helen’s fingers came to a stop as well. “Never? You poor thing. You’re clearly so…ummm… gifted,” she offered looking for the right words. “You should be sharing your gift, not keeping it locked away.”

A bit more at ease now, her affirmations helping distill the awkwardness in the air, but still self-conscious, “It’s not that I don’t want to… I really want to… I just… I just haven’t been… ummm… I’ve never had the chance.”

“Would you like the chance right now? I want to know what that glorious, hard teenage cock of yours feels like. I want to teach you how to use your gift.”

Without another word, Helen moved onto her hands and knees and crawled across the bed. Her large soft breasts drooped, erect nipples grazing against my chest as she hovered over my naked body, leaning in and placing her lips on mine. They were softer than I had imagined and felt tender against my own as she kissed me playfully sucking on my bottom lip. She pulled back,

“So what did you think of your first kiss?” she teased before returning her mouth to mine this time letting her tongue slip inside. I responded in kind, allowing my tongue to mingle with hers tasting her sweet saliva. I laid there awkwardly, hands still frozen at my sides, Helen taking the lead as I enjoying the new sensations.

Again, she broke the kiss, “you’re a good kisser did you know that? Now, again, this time use your hands. Run them through my hair and over my sides and back. Caress me, ok?”

“Ok,” I smiled back ready to touch her soft skin.

Once again our mouths met and tongues became entangled. As per her instructions I raised my hands, stroking her slightly greying dirty blond hair. It was silky to the touch as my fingers combed through it and without breaking the kiss, Helen purred approvingly. I didn’t linger though. Feeling proud of the response my touch had elicited, I moved my hands to her slender shoulders. My big hands first stroked down and back up her arms, which she was supporting her weight on. The, I moved them along her sides, the heels of my hands coming into contact with the soft flesh of her hanging breasts, my fingers curved onto her back as my hands glided down to the small of her back, over her hips, and then back up again.

Helen slipped one hand between us and I felt it move over my flat stomach. Not breaking our kiss, my hands still stroking her smooth skin, she wrapped her small hand around the base of my shaft and began pumping softly. I responded by moaning into her mouth.

Finally, our lips unlocked. Helen’s hand continued to pump me as her mouth moved to my ear. She whispered, “You feel so big in my hand, I want to taste you.” Then, slow and purposefully, she kissed and licked my ear lobes, then down to my neck, and across my chest. She stopped to give attention to each nipple, swirling her tongue and kissing the hard little sensitive points sending electric shocks through my inexperienced body.

I sighed in delight. I had no idea my nipples were so sensitive or could be touched like that. Never once in all the videos I had watched, had any of the girls taken this much time or care. Usually, they would just drop to their knees and swallow the already hard, veiny dicks, bobbing their heads and choking. But, not Helen. She took her time savoring each reaction she elicited, allowing me to savor each one of her touches taking her sweet time before working her way down my stomach, lapping at the dried semen from my earlier solo performance, and arriving at the base of strained, erect cock.

She planted several kisses around the base as her hand released my shaft, letting my engorged purple head rest against my stomach, painting my navel with my dribbling precum. She gently kissed my swollen balls, ticking the taught skin of my scrotum, before once again cradling my shaft in her petite hand. Gingerly holding me, Helen moved her kisses along the sensitive underside, gradually scaling the length. Upon reaching the top, she opened her lips and closed her mouth around the plump head.

“Oh god, Helen… that feels incredible.”

Helen responded by increasing pressure, sucking with more immediacy, her tongue gently stroking my frenulum, her hand pumping around the base. Each tiny gesture brought me closer and closer to the edge and my inexperienced cock felt like it was going to explode. Helen could sense how close I was and removed her lips, pumping my cock a few more times for good measure as she sat up on her knees and smiled.

“Wow… I was just about to—“

“I know, sweetie,” Helen interrupted. “That’s why I stopped. You need to learn how to control it. Now, breath deep. That’s it. Relax. Good. I’m not done with you yet.”
The immediate urge to spill my seed subsided as I listened and followed her instructions. With each long exhale, I felt my body relax and I regained control over my senses. Yet, somehow I was harder than ever, feeling a pressure from inside that was trying to expand the already strained skin that encased my manhood.

“Now,” Helen instructed as she laid back spreading her legs wide, her glistening sex on full display. “It’s your turn. Remember, honey, take your time just like I did. There’s no need to rush. Enjoy each moment.”

I did my best to repeat Helen’s graceful and purposeful action admittedly feeling self-conscious in my earnest attempts at being sensual. Nevertheless, I slowly kissed her ears and neck before coming to the swell of her large, matronly breasts. Her tense nipples jutted upward, inviting my touch. With the ineptitude of an amateur about to feel his first breast I squeezed my hands around either side and felt her nipples press against my palms.

“No, not like that,” Helen chided. “Remember? Gentle… good. Like that. Don’t touch my nipples yet… make me want you to touch them. Make me excited. Work around them. Kiss the areola, but not the center. Kiss the space on my chest between my breasts. Let me feel the size of your strong hands, but be gentle. Yes, yes… just like that.”

I followed her instructions again, doing my best to restrain myself. I felt her soft breasts, experiencing their weight, caressing and cradling the curvature in my palms. I proceeded to plant kisses over her flesh exploring every inch of her mature globes, carefully avoiding the hard nipples as she had requested.

Helen moved her fingers through my hair, breathing audibly in a deep, steady rhythm. “Now,” she whispered. “Suck on my nipples…. Ahhhhh…. Yesss!”

Helen squealed in delight as my lips closed around the strained pebbly skin of her fully distended nipples.

“Yes… yes…” her breathing becoming more rapid. “Now use your tongue. Fuck… yes, like that. Now the other side…. Right… mmmm…. Use your fingers. Pinch me… not hard… like that… uuhhhhhh!”

Helen’s mature form tensed, her breathing increased, and with my mouth still latched, she let out a long growl emanating from someplace far deeper than any sound she had made thus far. I was taken aback and thought to pull away, but Helen’s hands held my head firmly in place until her body was able to relax. Finally, she let go and I lifted my head.

“You’re such a good boy. Look,” Helen instructed, pushing my head towards her pussy. “Do you see? You made me cum.”

I brought myself up so I could see between her legs, and sure enough, her swollen lips were coated in a visible covering of sticky fluid and there was a wet spot on the sheets.

Amazed at what had just occurred, I stammered, “I never knew… I mean, is that… do all women cum like that when you play with their boobs?”

Helen laughed, “Don’t call them boobs, honey, ok? Boobs are silly things. Call them breasts or tits if you must. Just not boobs. And no, not all women’s breasts are so sensitive. I guess I’m just lucky,” she added with a giggle. “But,” she continued, “If you take your time like that with a girl your age, she may not cum, but I guarantee she will be very, very appreciative. Now, why don’t you clean up that mess you helped me make between my legs?”

Now, I had yet to admit this to anyone, but more than wanting a blow job, possibly more than wanting sex, really, more than anything, I wanted to see what a pussy tasted like. Ever since I had first come across those tapes in the back of that closet and discovered that a vagina wasn’t merely a simple opening, I was fascinated. I would watch lesbian scenes on repeat, the women cooing things like, “oooh… you taste so good” as they lapped away at their partner’s sticky sex. What was that taste? Well, I was about to find out, my cock a column of pure steel with the very thought.

I lowered my head between Helen’s white creamy thighs and for the first time in my young life, I was confronted face-to-face with a real life vagina. The intoxicating aroma I had previously inhaled on her discarded underwear was now far more pungent and enticing. Helen reached both hands between her legs and pulled apart her meaty, wet lips, allowing me a better view of all the parts of her sex. A string of her cum stretched across the expanse of her opening, glistening as the light reflected off of it. The tiny rosebud of her engorged clit, barely visible, escaped the confines of its hood.

“Do you like what you see?”

I nodded unable to muster a verbal reply, salivating at the thought of tasting her.

“Just like with my breasts, take your time. I know you want to dive right in, but kiss the outside first. Build up my anticipation. Ok?”

I lowered my head and began to kiss and lick around the soft fur coating of her vulva and outer lips. I placed gentle kisses above and below her fleshy folds, her wet opening taunting me, daring me not to lick it. The taste of her juices, which had escaped her during her orgasm lingered in her pubic hair. Was this what pussy tasted like? It was mostly sweet and little bit salty, and although not immediately appealing, somehow addictive. God, all I wanted to do was pry her lips apart and burry my tongue inside, but like a dutiful student, I paced myself and waited for my teacher’s instructions.

“Ok… that’s it… nice and easy… tease me. Girls loved to be teased when you do it right. Mmmmmm… do you see how wet I am? OK, now, gently, spread me apart and put your tongue inside me… mmmm… careful, don’t touch my clit yet.”

I followed Helen’s directions and eased apart her lips, my tongue making contact with her innermost parts for the first time. She gasped at my tongue’s touch and proceeded to exhale slowly as I began to explore her folds. I slipped deeper inside her, my tongue repeating the motions I had previously tried when we had first kissed, my nose in her bush, my chin grinding against her slickness with each movement. I did my best to coax out her honey, as once again, her hands found their way to my hair.

“Your tongue feels so good, baby… uhhhh… I love the way you eat my pussy. I’m ready. I want you to use your fingers to pull my hood back so you can suck my clit.”

Again, I was apt to follow her instructions, eager to please my teacher. I pulled her further apart and the fleshy pearl that had until this point merely been peeking out, was now fully exposed. My lips closed around the button and again, Helen gasped with a sharp intake. I sucked on her gem, varying pressure gauging her responses, seeing how to proceed.

“Use your tongue now, baby… that’s right…mmm….good… use tiny circles… now the other way… fuuuuuck… yesss.”

My tongue swirled around and round polishing her treasure causing Helen to throw her head back in ecstasy. Her hands were now clenching my hair, pulling my face hard against her.

“Yes! Yes! Yes! Yes!” She panted in short bursts. “Fuck me with your fingers!”

My index and middle fingers slid easily into her soaked opening, her tight walls dilating to accommodate them, almost pulling me in. I’m not sure what I expected it to feel like, but nothing could prepare me for the actual tactile experience of feeling the warm wet recesses of her pussy.

“Yeeessssssss!” Helen blurted. “Move your fingers. Yessss! Like that… like you are saying, ‘Come here.’ Fuuck. Oh that feels so good!”

I obliged Helen’s ever command, interpreting her instructions to the best of my ability. Her body was writhing in pleasure.

“Yes baby! Don’t stop! No matter what I do, don’t stop until I tell you!”

Helen’s body tensed and I felt her pussy walls contract around my fingers. Her hands pulled me even tighter and her legs clamped shut around my head. Though muffled by the flesh of her thighs, I could still make out her primal moan as she began to cum violently releasing a surge of pungent juices against my face and fingers.

Helen hadn’t said to stop yet, and so, squeezed between her legs, practically suffocating I did my best to hang on and lap up everything she offered as her up as she bucked and jerked spastically. Wave after wave crashed over Helen’s body and her sex continued to twitch.

Finally, after several minutes, she relaxed her legs. “Mmmmmmmmmm…That was exactly what I needed.” She sounded drunk and dazed. “Ok sexy. You can stop now.”

I relinquished her clit and slowly withdrew my fingers from her sopping hole, her full pink lips latching on to fingers as long as they could. I looked up from between her legs, her hands still in my hair. I couldn’t hold back the ear-to-ear grin, which had spread across my cum covered face, so pleased with myself.

“See baby… look what happens when you listen. You’ve already made me cum twice and I haven’t even felt that big, young cock inside me yet.”

By this point, I was so hard it was almost painful, my cock extending forward from my body like a boy on his tip-toes straining to grab the cookie jar on the top shelf, just out his reach. Helen pulled my head back up, instructing me to kiss and touch her body until my lips found hers again. We kissed passionately and sensually, taking our time with little sense of urgency, simply enjoying each other. I was concerned about the taste of her cum on my tongue, but she just moaned in delight when she got to taste herself on me.

Still kissing, Helen reached down between us to once again take hold of my aching cock, her cool hand causing me to twitch as she wrapped her fingers around the hot, taut flesh. She guided me towards her entrance and placed the tip of my cock at her opening, not allowing me so slide in, rather moving my head along her slick splayed lips, letting my precum mix with her juices. I could feel the heat radiating from her pussy and I wanted to dive in, but she just kept teasing me while concurrently working herself back up.

Breaking our kiss, she whispered in my ear, “I’m going to let you inside me now, ok? But, slowly… don’t just jam the whole thing in… make me want it all, make me beg to be filled. Do you understand?”

She lined me up and encouraged me to push past her petals, letting my cock sink into her warmth. I sighed, completely overwhelmed by just how hot and wet it felt. Helen wrapped her hands around my back, pushing my chest against the cushion of her breasts, her nipples pressing into me.

“There you go, baby… hold it there… now, nice and slow… in and out… not all of it… just a little. Let me get used to it”

With each stroke I slid deeper and deeper in to the depths of her womanhood. As much as I wanted to jackhammer away, like all the muscular meatheads I had seen in the videos, I maintained control, allowing us both to enjoy the sensations of our bodies fully interlocking. Helen coached me, encouraging me like a cornerman coaching a boxer to use his footwork and jabs in order to set up a knockout blow.

“Mmmm… that’s it, tease me. God, your cock is filling me up… do you feel how tight I am around you? I bet the girls your age couldn’t even take you… Go deeper now, go all the way.”

I let myself sink in further, her steaming pussy a quicksand trap for my manhood, gripping me and pulling me down until our pubic bones met and I was fully inside her. Once again, Helen’s walls contracted, constricting around my entire 8” as held me there, kissing me deeply, allowing another small orgasm to ripple across her body.

Once the slight tremor subsided she began to instruct me again. “Grind against me. No need to thrust yet. Just, keep yourself deep inside me. Let your pelvis grind on my clit… yessss… like that…. Fuck, you feel amazing.”

Again, I did my best to absorb every word she uttered and execute exactly what she wanted. Her hands were now grabbing my buttocks and holding me against her. A consistent stream of moans escaped her lips, back arching, head tilting elongating her neck. She clearly loved the feel of me inside her combined with the friction on her swollen clit.

“Now fuck me, sweetie. Use long strokes…. Still not too fast though…mmmmmm… yes, maintain control… use every inch of that glorious cock.”

I placed my hands firm on the mattress on either side of Helen giving me the leverage do pull out and then drive myself back in. The sensations were tremendous, feeling the slick walls of her pussy cling to every inch of me. I kept a steady rhythm, Helen encouraging me to keep tempo.

“Hear the music, baby. That’s it… it’s a dance. In and out. In and out,” she counted—a conductor keeping time for our symphony of sex. “Can you feel it? Keep grinding and rocking your hips with each stroke… Uhhhh…. Like that… yesss…”

Her count increased as the tempo ramped up and my movements matched. Faster and faster, not a ferocious jackhammer, yet plowing into her with long, quick powerful strokes.

“Fuck, Helen,” I let escape my lips, now breathing hard and starting to sweat. I was in heaven; this was better than I could possibly imagine. “I.. I… I think I’m gonnna cum…”

“Not yet, baby,” she exhaled back, “keep control… you can do this… relax and breathe with me… focus.”

I did everything I could to keep from spraying my seed deep inside her at that exact moment. As a kid, you always joke to think about baseball to take your mind off of the immediate need to explode, but Helen encouraged me to focus, to remain relaxed and in control over my body, to be completely in tune with the moment and with my lover.

“I’m going to cum, lover,” Helen gasped. “I want you to cum with me, ok?”

I was in no place to argue. Even though I had always fantasized about pulling out and spraying my cum over her face and body like they do in the tapes I had watched so many times, I listened to what Helen instructed. I thought the tapes had prepared me and taught me what I needed to know, but this was a whole new education and I was determined to be an apt pupil. Everything Helen had told me so far had both felt amazing and seemed to drive her crazy.

Her breath quickened and I felt Helen’s nails dig into the sweaty flesh of my back as her legs wrapped tight around me holding my cock deep inside her. Already an impossibly tight fit, her pussy flexed and clamped down around me, clasping my erection like a boa constrictor trapping its prey as she came with tremendous force.

Her velvety walls began to undulate, coaxing my cum to bubble up and finally, with Helen deep in the throes of her powerful orgasm, I erupted inside her.

“Fuuuuuhhhhhhckkkkkk….”I exhaled as I expelled my spunk into her hungry cavern. Her body, overcome with spasms while her pussy milked my teenage cock, drawing out every last drop of my seemingly endless stream, as I delivered my full load. I collapsed on top of her, short of breath, both our bodies still experiencing the slowly diminishing ripples of pleasure. Her body trembled; my cock twitched; we melted into each other in the afterglow of our shared climax.

As I regained consciousness I could feel the physical mixture of our joint orgasm leaking down and around my softening member. We kissed again and I rolled off of her, my cum covered cock finally able to slip free from her greedy grip. As I lay next to her, the smell of our sex hanging heavily in the air, I watched Helen reach down to run her fingers through the sloppy evidence of our lovemaking. She coated her fingers in our combined fluids before bringing them to her lips.

“Mmmmmm….” She grinned cleaning off her fingers. “We taste so good together.”

We continued to lay there quietly, completely satisfied. My mind raced, replaying the night’s events over and over again. Did this really just happen? After all these years… I mean, I had never even kissed a girl and now, in one night not only did I have my first kiss, but I had my first women. It was a night of a lot of firsts I supposed—I was no longer a virgin. And then a new thought overtook me.

“Oh my god, that was incredible. But, shit! What about Stefan?” I worried aloud, “He must’ve heard everything!”

Helen laughed, “Don’t worry, my love. Stefan isn’t home tonight. You know, I’ve been waiting for us to be alone for a few nights now. You think you are so clever, staying out late and creeping back into the flat at all hours. I hear you tip-toeing around. This isn’t the first night I’ve caught you jerking that big dick.”

Quickly, I reverted back to the awkward, easily embarrassed teenager of only a few hours prior. “It isn’t?

“No, sweetie. This is just the first time I’ve been able to actually do something about it.” Helen kissed me again her soft, naked body curling up against me. “You know,” she added with a chuckle. “With a little more practice, I think I can make you into quite a good lover.”

—-

For the next few weeks, until my stay in Berlin had to unfortunately end, Helen and I found every excuse to be alone whenever we could. I would leave school early to meet her during the day or Helen would do what she could to try to gently encourage Stefan to go out and crash at friends’ houses—whatever it took. We continued to explore and experiment, Helen coaching me, constantly teaching me new tricks. We tried multiple positions and places—I fucked her from behind in the shower; she rode me while sitting on the living room couch; I buried my cock in her nurturing pussy while I stood in front of her in the kitchen, her body laying across the table. She even let me pull out and shoot my cum all over her body just like I had seen. Sure, Helen showed me techniques, but more importantly, she taught me how to be a lover.

—-

Things for me changed once I was back in The States. I was no longer shy or nervous around the girls my age and they immediately picked up on my new found confidence. Within the first few months back, I slept with three girls, fucking them each with a level of expertise and control that they had never experienced. But, the satisfaction was brief. I took immense pleasure in watching these young girls squirm and scream in glee, knowing that I was causing them to have these earth shattering orgasms. But there was no connection. My practiced skills may have been matched with effort, but never once were they reciprocated with equal technique or care. And, most importantly, I didn’t actually care about these girls.

David Foster Wallace once wrote that there are two types of misogynists in the world: one who puts a notch in his bedpost for every woman he beds and one who puts a notch in his bedpost for every orgasm he can give to one woman. I have always related to the latter. Which is why after that initial summer of meaningless sex, I embarked on a series of monogamous relationships where I could continue to hone my skills and explore possibilities with someone that I trusted. For some reason, however, these relationships never seemed to last more than a few months, which I never understood. After all, I was a sensitive, creative guy who never cheated or wanted one night stands.

This pattern continued through college and into my early 20’s. It was rare that I didn’t have a girlfriend, but even rarer for a girlfriend to last more than a few months. At the same time, I needed to start making adult decisions about my life. Aside from my incessant lovemaking, I most of my efforts were focused on working on music and painting. I was broke, but mostly content. Eventually, however, even my incredibly supportive parents said that I would need to figure out a way to earn a decent income.

I applied for a low level creative position at an advertising firm figuring I could use my creativity and actually earn a living wage. I quickly worked my way up through the industry, first assisting and then leading on several successful campaigns making a series of jumps between agencies each with a raise in salary and title. I became very comfortable getting what I wanted, eating at the finest restaurants, and buying only the best. I educated myself on fashion and design, purchasing new designer clothes and covetable furniture. I filled my life with impressive, beautiful things.

And, I was happy, I think. I mean, what else could I really want? Sure, I rarely played music or painted anymore, but I still listened to music all the time and I had a fairly impressive art collection. Everything was wonderful except I still hadn’t found a consistent longterm partner to share it all with.

To be continued…

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