Stories from my youth – taking my lesbian best friend’s virginity [MF]

Well, I guess the people have spoken and I’m listening. You all wanted more stories from my younger days so here is one of my personal favourites. This particular story comes from my late teens, when I was a sheepish nineteen-year-old freshman taking my first steps into adulthood at Rice in Texas (still got my blue and grays, go Owls). Houston was my home city and I was proud to be the first man in my family to go college – my father was a coal miner and my mother stayed at home to look after me and my three brothers. For those that asked about me last time I posted – I’m light-skinned African American (compared to my dad who is blacker than night) 6’4 and built big like my father.

This story, as all good stories go, begins with a girl. Her name was Emma, but we called her Em for short. She was a part of my social circle growing up in Fresno, and she stood out for being one of the only white chicks that hung out with us in high school. I first met Em through my mutual friend Grace, when she dragged her along to a party in our senior year. Grace was short and fierce even back then, and she pretty clearly knew what she wanted from life. Never one to beat around the bush, she came out to me as being gay early in our freshman year which came as no real surprise to me at all. Grace had always kept her hair short and was the tomboy of our group, so her telling me she was a lesbian barely even registered for me. I was raised in an open and accepting family that taught me to respect people’s choices so long as they didn’t force those choices onto me, so having a lesbian as my best friend was actually pretty advantageous. For starters, Grace was a social magnet – everyone in our school knew who she was and she had this uncanny ability to create “hangers-on” – people that were drawn to her charisma. Her mother was also a salacious divorcee that famously didn’t mind kids getting drunk at her house so long as she could “keep an eye on us”. This naturally resulted in Grace’s house being the central party house for most of my high school years, with people flocking there at least once a month to get drunk and have their first sexual experiences.

The night I first met Em was one of these parties, with thirty or so eighteen-year-olds drinking the cheapest liquor they could find and nervously fingering each other in the bushes. Emma stood out, not only for her skin colour but also her natural confidence and laid back demeanour. At a time in my life where everyone around me was trying their hardest to conform to whatever the latest social norm was, Em was operating on a whole other wavelength. She knocked at the door and Grace answered, throwing her arms around Em and loudly screeching. Em smiled slyly and hugged her back, before stepping into the house and turning to face me. Emma was a short girl, maybe 5’4 and looked like she had an athletic build. She had firm looking breasts that were well hidden beneath her loose-fitting top, and wide hips with a round ass. Her eyes were bright blue and her light brown hair was tied up in a tight ponytail. Grace introduced me to her and she flashed me her pearly white smile for the first time. Emma had one of the purest smiles I have ever seen – perfect white teeth with plump full lips. From that moment I knew there was something truly unique about Em, but before I had a chance to even speak a word Grace had whisked her away into the mass of sweaty bodies and I was left with the lingering smell of her perfume. I can still remember the smell today – a mixture of floral with a sweetly spiced afternote.

Grace and Em were a “thing” in a matter of weeks. Speaking honestly, I didn’t expect Emma to bat for the other team given her style and mannerisms, but I suppose the joke was on me for thinking that all lesbians were required to have short hair and listen to punk rock. Grace and I were relatively inseparable from our early teens, so Emma very quickly became a part of my daily life. She and Grace were always holding hands and cuddling up to each other on the sofa in her mom’s basement, which bothered me at first but I quickly grew used to being the third wheel in their relationship. We would often go on day trips out to Wolf Creek Park once Grace finally got her drivers license, spending the day out near Lake Livingston.

Because Grace and I had been best friends for so long, she considered me as a brother to her, and I felt the same way. She and I talked about just about anything, including openly discussing our sex lives. Being a gangly eighteen-year-old starting to fill out my football jersey I was finding my footing sexually at a relatively normal pace. I’d lost my virginity by 16 and had begun to explore some of my sexual preferences from there, finding out things that I liked and the things I didn’t. Similarly, Grace had also established herself sexually and knew what she liked and didn’t like. She confided in me that she had tried sucking a cock but quickly discovered she not only hated the taste of precum but also had a terrible gag reflex. By our senior year, Grace was a sexually confident lesbian that knew her way around a pussy (her words, not mine). Em, however, was about as innocent as the early morning light. In the early days of their relationship, Grace confided in me that Emma had no real idea of how her own vagina worked and required Grace to take her step by step in discovering her sexuality. For Grace this was exciting and stimulating, being the first and only person to please Emma sexually. Grace told me that Em quickly learnt her own likes and dislikes, and fast became something of a sexual deviant, eagerly experimenting with new things. Grace loved bragging to me of their sexual escapades, which was admittedly confusing for me as I felt a twang of guilt for being sexually aroused by her stories.

One summer’s day in January as the three of us were out at Lake Livingston nervously awaiting our college applications, I had an experience I will never forget. We had found a secluded cove up on the western shore of the lake, and the girls were keen to go for a swim. It was over 100 degrees out, and there wasn’t a soul for miles. Grace lay on the grassy embankment in her denim shorts and a bright blue tank top, with Em laying next to her in a short pink and light blue floral dress. Grace was upset because she had forgotten her swimsuit in her rush to leave the house after an argument with her mother, and Em was lightheartedly poking fun at her. Not one to be the butt of a joke, Grace stood up abruptly and in one fluid motion had removed her tank top, followed by her shorts. She stood in front of the two of us in her tight black panties and bra, and before either Em or myself were even able to comment, her underwear came off too.

“Skinny dipping time losers”, Grace teased as she turned around and began walking purposefully towards the shoreline. Grace was shorter than Em, and had the typical curves of a dark-skinned girl, with huge hips and a fat ass. She paused as she reached the water’s edge, turning back around to face Emma and me. Her breasts were plump and round, and her large dark nipples had hardened to little points. She was clean-shaven, with ever-so faint little goosebumps on her mons pubis from razor rash.

“Are you fuckers joining me or what”, she said with her typical sass. Emma stood up before I did, almost as if I wasn’t even there. She lifted her short little summer dress over her head, revealing tight-fitting light green panties and no bra. I was to her left and slightly behind her, so I couldn’t see her breasts fully, but from the side, I could see how perfectly they sat, with just the slightest sag. Her skin was far more olive than I’d ever realised, with her breasts a lighter colour than the rest of her body. I could see one nipple at the tip of her left breast, darker red in colour and perfectly proportioned to the rest of her large breasts. She slid her fingers inside the edges of her panties and slipped them off with a little wriggle, bending over ever so slightly to finish taking them off. Her ass was perfect. There was really no other way to describe it. Round, tight and similar to her breasts, a lighter tone than the rest of her skin where she had sunbathed in bikini bottoms. Emma walked towards Grace, still standing at the shoreline stark naked.

“What’s the matter, you scared we’ll see your saggy ballsack or something” Grace teased. I knew I would need to be strategic about this, as my cock was standing firmly to attention watching Emma’s tight, naked athletic body walk away from me. I stood up slowly, leaning slightly forward to conceal my rigid cock. I quickly pulled off my t-shirt, followed by my gym shorts and briefs in one go. My hands instinctively reached down to cover my cock and balls, and I began to awkwardly shuffle towards the two naked girls. I should clarify that despite my skin colour, I have a very average-sized cock. I’ve been told it’s slightly thicker than most, but it’s around 7 inches erect and has always gotten the job done. This being said, I had tucked it up against my stomach and cupped it with both hands as I reached the water’s edge and stood next to the girls. Grace looked down at my covered penis and balls and laughed, reaching forward and slapping my hands away.

“Fuck outta here with this covering up shit” she laughed, as my cock briefly sprang out from between my hands and pointed straight at Emma. I mumbled something incoherent and placed my hands back over my cock, but not before Emma had turned to face me, eyes locked on my throbbing rod. She giggled and looked back up at my face, before turning back towards Grace and shoving her into the water playfully. Grace fell backwards into the cool water, shrieking. She stood up, dripping wet, and lunged at Em, dragging her into the water with her. I decided my best bet at covering up my raging erection was to join them in the water, so I jumped in next them. We swam out from the shallows, the girls playfully splashing water at each other and joking around. I was somewhat preoccupied with the stiff pole between my legs that was mere inches away from the girls naked bodies underwater. The last thing I wanted was to prod one of them by accident, but as we fooled around in the lake I began to forget about my own body and focused more on what little I could see of the girls’ breasts under the slightly murky water. Emma’s tits were more buoyant than Grace’s, with her dark red nipples often breaching the surface and reinvigorating my erection. After we’d swam around for a while the girls started to swim back to shore, and I followed. Grace got out first, her round black ass wobbling as she walked up the grassy embankment. I watched the water drip down the contour of Emma’s round ass cheeks and down her thick olive thighs. As she reached our belongings Grace threw her a towel and she wrapped herself up in it, still facing away from me. I remember feeling cheated for not getting a glimpse of her pussy. We wrapped the day up and drove the couple of hours back home, me with a mind full of jerk off material that would last me months.

Two months later, on what had otherwise been a rather uneventful Monday evening, I heard a knock at my front door. My family was out of town for the week at my uncle’s house, so I had the house to myself for the first time in months. Not expecting any visitors, I was confused, but as I peeped through the eye hole I saw Emma standing on my doorstep. She was wearing denim overalls and had her hair down loose around her shoulders. I opened the door and she immediately hugged me, wrapping her arms around my waist. “What’s wrong Em?” I asked her nervously, thinking that something awful had befallen her.

“She fucking cheated”, Emma stammered. I knew Grace was sexually promiscuous, but I genuinely thought her and Emma were in it for the long haul. “Jesus” I muttered, not really knowing what the fuck I should be saying to her in this situation. “Come inside” I offered, as Emma detached herself from my waist and followed me inside the house. I invited her into the living room, where she sat down on my couch and told me everything. She had read Grace’s texts from another girl and confronted her about it. Grace, in all her typical alpha female bullshit, denied any wrongdoing right up until Emma snatched her phone from her and brought up the lusty conversation with the other girl on the screen. They had a nasty exchange and Emma left in tears. To Emma, Grace was her world. She didn’t have any other friends aside from Grace and myself, and so she felt she only had one place to turn when things turned sour. I let Emma cry softly into my shoulder for an hour or so until she got all the emotions out of her system, before suggesting that she stay the night and we play some video games to get her mind off of Grace. For the first time since she had arrived, Emma looked up at me and smiled. We went to my room and I booted up my PC, setting her down at my desk and showing her the ropes of how to play the new Tomb Raider game. We laughed and played video games for hours, eventually stopping to order some pizza and chat some more. Emma confided in me that she was feeling trapped in her relationship with Grace for several months at that stage and that finding out she was cheating almost came as a relief to her. I did my best to listen to her grievances without taking a side or shitting on Grace too hard, but I knew that Emma could do so much better than Grace.

Eventually, after Emma had finished the first part of Tomb Raider and the hour was getting late, we decided to call it a night. Up until that point I hadn’t actually considered where she would sleep, but it occurred to me that I should offer her my bed and I would sleep on the couch. “I’m happy to sleep on the couch and you can have the bed” I said.

“No way, I’m not kicking you out of your own bed!” She said earnestly. My bed was a king single, which was comfortably big enough for me but would be a tight squeeze for the two of us.

“Well, if you’re sure” I said. “Do you need something to sleep in?”. It was a balmy night in Texas that night, and the house was a pleasant 68 degrees. “If it’s cool with you I can just sleep in my underwear,” She said nonchalantly. I felt my cock twitch ever so slightly but stifled it and went to make the bed.

I took off my shorts and shirt and climbed into bed, the glow of my PC standby lights illuminating most of my bedroom. Emma stood at the edge of the bed and unbuckled her overalls, letting them slip to the floor. Beneath she was wearing a dark long sleeve top and dark panties, which she left on as she climbed into bed next to me. She half nestled herself into my body, resting her head on my shoulder. I could smell her fruity smelling shampoo in her hair, and the subtle smell of her perfume lingered on the thick night air.

“Can I ask you a bit of a weird question?” she said softly.

“Of course, shoot” I replied.

“It’s really weird though” she cooed, “promise you won’t laugh at me”.

“Promise,” I said earnestly.

“Ok, so…” her voice trailed off briefly. “What does it feel like to get a blowjob?”

Immediately I felt the blood rush to my ears as I tried to think of a reply. My cock began to stiffen in my briefs and I felt my balls tense up. “It’s kinda hard to describe actually,” I reflected. “I suppose the first thing you feel is the warmth of her mouth around the tip of your dick”. I felt odd saying the word dick out loud.

“What about it makes it feel good though?” she pressed.

I had to really focus on forming a coherent reply as the blood rushed from my brain. ” I guess the feeling of something wet and warm surrounding my cock is what makes it feel good.” I paused for a moment before continuing. “The feeling of constant pressure is also what makes it feel good. Like, the girl has to suction onto the cock as she’s doing it”. Emma didn’t reply. I began to feel waves of nervousness rushing over my entire body. Had I over-explained? Was I too graphic?

Emma moved her head slightly on my shoulder. “I’ve always wanted to try giving a blowjob”.

This took me by complete surprise. My cock filled my briefs and I could hear my heartbeat in my ears. “Have you ever seen a real-life dick before?” I asked.

“I mean, I’ve seen my dad’s when I was younger but I don’t really think that counts.”

“I guess it doesn’t” I agreed. My brain was now located firmly inside my throbbing cock. I wasn’t thinking straight at all. “This is probably going to sound really weird,” I said, “So feel free to say no if you don’t want to… but do you want me to show you mine?” The words had barely left my mouth before a wave of anxiety rushed over me. What the fuck was I saying. Who the fuck offers to show their lesbian friend their cock? What the fuck was wrong with me.

“I mean…” she paused. Time felt like it was standing still. “If you’re comfortable with it then so am I.”

My body reacted faster than my brain did, reaching out to turn my bedside lamp on. Warm yellow light flooded my room, stinging my eyes briefly. My cock stood upright like a tent pole in my briefs, as I moved my hands down either side of my waist and pulled them down. My cock sprang out from underneath them and stood firmly upright, the tip glistening with a layer of precum. Emma’s eyes were locked on my erect penis.

“It’s kind of magical how hard it actually gets,” I said, like some kind of perverted science fact. “There’s a reason they call it ‘rock hard'” I joked. “Here”, I guided her left hand down next to it. “Try squeezing it right there in the middle.”

She extended her fingers around the base of my cock and gently pinched it between her thumb and pointer. My cock couldn’t have been harder if I tried.

“Fuck, are they always this hard?” she said with a tone of genuine interest.

“Well, not always,” I said. “But when they’re fully erect they get pretty solid.”

She gently squeezed my cock again, this time slightly firmer. My cock twitched, like a bull at the gates. Emma gasped quietly.

“Fuck, sorry,” she said. “Did that hurt?”

“No no,” I reassured her “They just sometimes do that”.

“Why does the tip look like it’s wet?” She asked.

“That’s just precum, I guess it’s similar to the way your vagina gets wet when you’re excited”.

“I think mine is wet right now,” she said, almost matter-of-factly.

I decided to shoot my shot. “You know, I’ve never gone down on a girl before,” I said. It was a bald-faced lie, but it was worth a try.

“Seriously?” Emma sounded surprised. “I thought you’d done everything before”.

“Not really,” I said. “I’m kinda inexperienced actually”. Emma was quiet for a moment, before lifting her head off my shoulder and sitting upright in the bed.

“Want to see mine?” She asked, with pure innocence.

I had to contain my excitement and play it off cool, like I wasn’t about to explode all over her pretty dark green panties. “Sure, I guess”, I said nonchalantly.

She lay back and slid her panties off, pulling them off of her ankles and throwing them on the floor next to the bed. She lay on her back, brought her knees up and spread her legs. My mind was going at a thousand miles an hour – I was acting before I was thinking. I scooched down the bed and across slightly, laying on my stomach with my head between her thighs. I stared up at her pussy. She had short dark brown pubic hair on the top of her vagina, with a few stray short hairs further down beside her pussy lips. The lips themselves were puffy and dark red, with her lighter pink inner lips barely visible between them. She had a perfect pussy. She reached down with her right hand and slid a finger between her outer lips, teasing them a little and briefly exposing her inner lips. The smaller pink inner lips glistened with her grool, as her finger became coated in a light sheen of pussy juice. She slid a second finger between her outer lips, spreading them to reveal her creamy inner pussy. I was so close I could smell the familiar earthy, sweet aroma of her vagina, as she spread herself for me. I could clearly see her pussy entrance and she slid a single finger inside, letting out a small moan.

“How many fingers can you fit inside?” I asked.

Without missing a beat, Emma replied. “Four, five if I’m really horny”.

“Fuck, show me,” I said. Emma slid a second finger inside herself, followed by a third. She began to curve her fingers to fit the fourth finger inside, spreading her pussy wide. As she slid all four fingers in and out slowly they became covered in her thick white cum. She slid them out all at once, bringing her cum soaked fingers up to her mouth.

“I fucking love the way I taste,” she said, as she placed each finger in her mouth one by one and sucked her cum off each.

“Can I taste it?” I asked. Instead of replying, she ran her hand through my hair and gripped my head, pulling it into her wet pussy. My mouth was smothered into her dripping wet pussy lips. I could taste her sweet cum on my tongue, as it explored the inside of her vagina. She let out a very loud moan and used her grip on my hair to push my face in deeper. I was desperate to taste every part of her, to explore every inch of her body. I ran my tongue over her clit, flicking it back and forth like a little ball. My mouth was watering as I swallowed mouthful after mouthful of her cum. I could feel her body tense up as my tongue slid in and out of her. I didn’t want her to cum just yet, so I pulled away from her and brought my body up between her thighs. I ran my face over her shirt, resting on her erect nipples poking through her top. I nibbled them gently, and she desperately whipped her shirt off, revealing her perfectly shaped breasts. I moved up even higher, bringing my face next to hers. I leant in and kissed her, her cum still dripping down my chin. She kissed me deeply, our tongues exploring each other. She pushed me away slightly and ran her tongue down over my lips and chin, licking up every inch of her pussy drippings.

My cock was less than an inch from her awaiting pussy hole. I decided to push my luck by rubbing the tip of my cock up and down along her wet slit. She wrapped her thick thighs around me, pulling me in closer, the first inch of my cock accidentally slipping inside her. I pulled out immediately, worried I’d gone too far. She pushed me off of her, and I lay on my side beside her. She nudged me onto my back, before swinging her right leg over me. As she straddled me in reverse cowgirl, she slid her ass up towards my face, shoving it right on top of me. As she did so, she leaned forward and gripped my cock firmly in her right hand. She lowered her face and pulled my foreskin back, running her tongue across the tip and licking off my precum. I was staring up at her gorgeous round ass, so I put both hands on it and forced her ass into my face. My tongue slid in and out of her pussy as she took almost all of my throbbing cock inside her mouth. As she sucked my cock, I put my right index finger on top her little puckered asshole, teasing it gently. She pulled my cock out of her mouth long enough to say “Shove your fucking finger in my ass”. I happily obliged, sliding my finger deep in her asshole as she resumed sucking my cock. As I fingered her ass I ran my tongue up and down her pussy, swallowing her sweet cum. I could feel myself getting close, so I pulled my finger out of her ass and tapped her gently.

“I’m close,” I said. She climbed off and then back onto me, facing forward this time. I could feel her warm pussy on my stomach, leaking her juices all over me. “Have you ever wanted to try sex with a guy?” I asked. She looked nervous, but she bit her lip and nodded. She lifted herself up back, using her hand to guide my cock along her slit. She looked me straight in the eyes as she lowered herself onto my cock, her eyes widening as she felt her entire pussy stretched out as I filled her up. She was so tight I nearly came straight away, but I took several deep breaths and started matching her grinding with thrusts in and out. I pounded her cunt as deep as I possibly could, matching her stroke for stroke. She had closed her eyes, her mouth slightly open in pure ecstasy. I could feel her pace increasing and I knew she was close. I was barely hanging on myself – my cock was aching to bust a nut inside her. “Fuck, I’m so fucking close” I moaned. She opened her eyes and looked down at me.

“You can’t cum in my pussy,” she said. I was so close to cumming I thought she might not have a choice in the matter, but she lifted herself up and slid my cock out. “Where should I cum?” I asked as my balls began to ache. Before I had even finished my sentence, she spat on her fingers, reached behind herself and used her spit to lube her asshole. With one fluid motion, she moved back an inch and guided my cock into her awaiting ass. I felt her tight little asshole resist my thick cock at first before she exhaled and relaxed her hole. My cock slid straight up inside her ass, and she removed her guiding hand and began grinding me hard and fast. Her right hand now reached around to her pussy, as she began furiously rubbing her clit. My cock had never felt anything as tight as Emma’s asshole before, and within thirty seconds she began to slam her ass down harder and harder on my cock as she started screaming. I couldn’t hold my orgasm any longer, and as I thrust my cock as deep inside her ass as I could, I felt her pussy squirt cum all over my stomach and chest. The feeling of her warm wet cum all over me was the last straw, as my cock erupted deep inside her tight little asshole, filling it with my thick cum. She let out an ear-piercing scream as we came together for what felt like a whole minute. Finally, after my cock had finished it’s last few twitches of cum inside her ass she rolled off of me and onto the bed, gasping for air. I watched as my cum leaked out of her asshole and down her thigh, a sight I’ll never forget.

Emma and I never dated, nor did we ever share another intimate night together after that one, but for me – I got everything I wanted out of her body. She went on the date girls all throughout college, but I saw recently saw that she and her girlfriend of four years just broke up. I guess if I can ever convince my beautiful partner to have a threesome I know who I’ll invite…

Source: reddit.com/r/gonewildstories/comments/juhbbh/stories_from_my_youth_taking_my_lesbian_best