This is my fourth story. All my stories have some preamble, I just like re-living the situations that led to the sexy events as well as the event. If you don’t care much for my descriptions and preamble, there’s a “>>>Sexy Story begins here” line. Names have been changed.
For those of you who have read my other stories, this is the second part of when I lost my virginity to a much older lady named Nadia, who was 29 when she took me out for my 18th birthday and gave me a lot of instruction. For those who missed it, Nadia is a six foot three, heavily pierced and tatted goth with black hair, hazel eyes and crazy curves. She wore a corset, mini skirt, thigh high platform boots, and a spiked collar for this evening, and was wearing heavy dark makeup and bright red lipstick.
After we were done with our tryst in the bathroom, Nadia asked me to go lookout for a good moment for her to exit the men’s washroom. A few customers walked past the doors, and then I motioned for her to follow me out. We made our way back to our table, and Nadia resumed drinking her drink as though nothing had happened. She had re-applied her red lipstick, and I kept finding myself staring at her lips, getting turned on again thinking about how that exact shade of red lipstick was still staining my cock.
Nadia made some idle chatter, saying that she liked this bar for the early evening, but that she much preferred another bar a few blocks further away. Nadia also mentioned that this next bar was a few blocks towards the hotel room she had booked, the key to which she had given to me already in my present, along with a pack of cigs, condoms, and a suggestive letter. We decided to settle up and move on to the next bar. (realistically, I would have gone anywhere Nadia suggested, I wasn’t going to argue with any suggestion she made.) along the way, Nadia told me to pull out the cigarettes, and she put two of them in her mouth. watching her lips wrap around the filters of the cigs was erotic, and she noticed me staring. “You okay there, hun?” she asked with a wry grin, as she lit up and offered the smoking cigarette to me. “more than okay” I reply, taking the offered smoke and taking a drag. I wasn’t a smoker at this time, and the smoke filled my lungs and I coughed and hacked. Nadia laughed, patted me on the back, and said “I’m glad I’m able to be your sexy guide into adulthood. Try to take smaller drags, and exhale quicker.” I followed her advice, and soon was puffing away happily. The mixture of nicotine, alcohol, and the adrenaline from my first public blowjob in a bar bathroom had my mind whirling, and I was on cloud nine. I think I was actually bouncing my steps, because Nadia kept looking at me and laughing, but I was at the sweet spot of intoxicated and was able to laugh along with her.
Eventually, we got to our next destination, and entered the bar. This time, I was ID’d by a heavy, tatted biker type, bald and bearded, sitting on a stool by the door. Nadia clung my arm to her, my elbow sinking into the side of her huge tits, and told the doorman “it’s his eighteenth birthday, I’m making him a man tonight.” This had me blushing and speechless, but the doorman looked Nadia up and down, looked at my ID, and muttered something, wishing me a good evening. “I don’t think he really wanted to hear that” I whispered to Nadia as we walked in, but she smiled and pecked me on the cheek. “no baby, that’s what jealousy looks like. If you’re gonna be out and about with a babe on your arm, you need to recognize it.” I tried to look back at the doorman, but Nadia was moving me along quickly. She found herself a seat near some pool tables, and pulled me in close. “do you have any cash on you, hun?” she asked, and I nodded. “great! Go get me something tasty. I will absolutely judge you on what you bring me, so make sure it’s good, okay?” she smiled, pecked me on the cheek again, and pointed out the bar to me. I looked over, and looked back to her. “how will I know if you’ll like something?” I asked, and Nadia laughed. “Hunny, girls want to be taken care of when they’re out with a guy. Its never a bad idea to ask a girl what she wants, but if you can bring her something she likes without her telling you, that’s huge brownie points.” She winks, and continues “like, getting blown in a bar bathroom kinda brownie points. Now go!” I turn around, and feel a slap across my ass. I look back again, and Nadia is looking at her phone with a smile on her face. She motions me away with a flap of her hand, and I walk over to the bar. There is a cute blonde working the bar, but I am more occupied trying to figure out what Nadia might like. I approach the bartender, and she is blessedly un-busy. She asks me what I want, and I explain that I’m trying to impress the girl I’m with, and that she told me I needed to get her something she would like, but didn’t give me any clues. The Bartender gave me a bit of an exasperated look, and I decided to try and pull a Hollywood move. I pulled a twenty-dollar bill out of my wallet and said “if she likes the drink, I’ll tip really well on the next one.” The Bartender shrugged and said “fair enough. Has she drank anything so far?” I raced through what Nadia had ordered before, mostly colorful drinks. “she ordered a pornstar. A green vodka drink. And a couple of shots of rum.” The bartender thought for a moment, and then made me up a blue drink. I thanked her, and started to walk away. I stopped mid step, turned around, and asked her “what’s this thing called?” she shrugged again and said “it’s a blue island. It’s got some of the same stuff as a pornstar, and it’s got rum.” She went back to cleaning glasses, and I walked back to Nadia. I put the drink down in front of her, and she smiled at me. “it’s very blue,” she said, and stirred the drink with her straw. “Blue’s usually good” she continued, and took a sip. She nodded, and smiled sweetly at me. “I like it! you did good! How’d you figure it out?”
Nadia had been very accepting of my inexperience so far, and every time I had tried to act cool for her I ended up looking and feeling silly, so I went for straight honesty. “I told the bartender what you had drank so far, and told her I’d tip her well if she gave me something you liked.” Nadia laughed and nodded. “Yup, that’s a pretty good strategy. Aww, I’m proud of you! Good initiative!” she laughed again, and then looked at the table. “hun, did you forget to get yourself a drink?” I looked down at my empty hands, and sighed heavily. Nadia broke down into further peals of laughter. “oh my god, you poor boy! You really are trying very hard, aren’t you?” I just shrugged. “I’m glad your having so much fun with this. Would you believe I’m usually not this dumb?” Nadia nodded again. “Yea, yea, I bet. Pretty gals can really mess a guy up. Go get yourself a drink hun.” I turn around and walk back to the bar. The Bartender looked at me walking up. “well? She like it?”
“Yea, she liked it” I replied, slapping the twenty down on the counter. “I’ll just have a beer I think.” The bartender asked me what kind, and I pulled a newbie move and asked her what they had. She sighed, heavily, and started listing off the domestics on tap. After the third or fourth, I stopped her and said “Sure, give me that one.” She filled a glass, and began to make change for my twenty. “nah, she liked the drink, the rest is a tip” I said, and she grunted a thanks at me. I walked back over to the table and sat down.
“so, are you having fun, hun?” Nadia asked me. I nodded. “so far? Best birthday ever.” Nadia seemed pleased with that, and we continued to drink for a bit. After the drink I brought her, she switched back to her go-to pornstar drink, but assured me the one I brought her was delicious. “I’m a bit older than most of the women you’ll probably be going for. I know what I like. Younger girls don’t know what they want, so you need to learn how to compensate for that.” I said something about how she might be giving me a preference for women her age, and she patted me on the back. “that’s the curse I’ve inflicted on you. You’re going to have a lot of fun, but it’ll be a while before you find someone who’ll fuck you as good as I’m going to tonight.” I replied “promise?” and Nadia laughed again. “you’re a quick learner, huh?” I smiled back at her, hoping I looked as confident as I was trying to seem.
>>>Sexy Story begins here
After more flirting and a couple of drinks, Nadia suggested we try to play some pool. I agreed, as I wasn’t bad at pool. We racked the balls, and Nadia offered to let me break. I sunk a couple of balls on the break, and Nadia clapped and cheered. Nadia was also not bad at pool, and we were neck and neck for a bit. As the game got closer to the end, Nadia leaned in and whispered “if you win, I’ll suck your cock again.” She brushed past me, letting her ass drag across my crotch. I was still a bit sensitive from our previous trip, and that bit of friction got me half hard again. “what if you win?” I asked, and Nadia winked and said “I guess you’ll have to return the favor.” The thought of eating her pussy got me even harder, and I lined up my shot. I was distracted with thoughts of Nadia, and I missed my shot. I stood up and sighed, and Nadia covered her mouth and stifled a giggle. She pointed down at the table, and I looked down, to see my fully hard cock hanging over the edge of the pool table, right under the light. I quickly adjusted, leaning over a bit to try and conceal it, and looked around. Luckily, the bar was pretty empty and the few people who were there seemed interested in their own chatting. I looked over at Nadia, and she winked again, and lined up her shot. her massive cleavage hung over the table, and she looked up at me, before pulling her corset down a bit more, exposing as much of her tits as possible. I could just see the dark brown of her areolas rising over the crest of her corset. She sunk the next few balls, and thanks to my throbbing dick and her excellent distraction, I lost spectacularly. She danced over to me, cheering her victory, and pulled me in close. “Guess you’re gonna be eating some puss hun. That okay with you?” I nodded, perhaps over excitedly, and Nadia seemed somewhat surprised. “Oh? Does someone like getting his face fucked?” and I said “yea, it’s may favorite actually.” Nadia said “I’m excited to see how good you are, then” and she pulled me towards the exit. “wait, aren’t – “and Nadia tsked me. “the bar’s been fun, but you’ve had quite a few. I want you alert for the rest of the night, and our hotel awaits.” We walked past the doorman, who looked Nadia up and down again. Nadia waved her hand and said “bye hun, have a good night!” and we stepped outside.
Luckily, the Hotel was only a few blocks away. Nadia and I made it to the door, and I fumbled the key out of my pocket. I opened the door, and Nadia stepped inside, and twirled around. “I’m gonna freshen up hun. Give me a few minutes.” Nadia looked me up and down, and bit her lip. “you still hard, baby?” the walk had taken a bit out of me, and I stammered “Kinda.” Nadia tsked and said “well kinda just wont do.” Nadia reached behind her, and unlaced her corset a bit. She pulled her breasts out, and I saw that not only were her dark brown nipples pierced, but she had tattoos covering the bottom half of her tits. She played with her nipples, and groped at her tits, and gasped and moaned exaggeratedly. Then she locked her eyes with mine and said “I want you to lay on that bed and stroke yourself. When I come back out, if you’re hard, I’ll suck your cock while I let you lick my pussy. If you’re not, then you’ll have to lick me until I say I’m done before I touch you. Understood?” I nodded, and began to undress. Nadia walked into the bathroom, and I heard the water running. I pulled out my cock, and began to stroke it, thinking about Nadia’s massive bust, imagining what her nipples with their little metal piercings would feel like in my mouth, imagining the taste of her when I got to lick her. it worked, and it took no time at all before I was raging hard. Nadia stepped out of the bathroom, wearing only her platform boots and some leather straps that crisscrossed her tattooed body. I looked over at her, looking at her thick, shapely legs, her hourglass waist, her big bouncing tits, and then finally her pussy. She had a thick landing strip shaved in, and I watched, mesmerized, as she walked toward me. she stopped at the foot of the bed, and put her hand underneath her chin, looking me up and down. She tilted her head to and fro, before hopping on the bed. She stretched her legs out, and lowered her head to my chest. She kissed my chest, licking my nipple, and then blew on it, making it hard. She brought her hand up and cupped my balls, playing with them gently. My hand was still around my cock, but I’d stopped stroking it as I watched her walk over. She leaned in, and nibbled softly at my neck, kissing and nipping me. “I want to see you stroke your cock while you watch me play with myself” Nadia moaned into my ear, and she slide a hand between her legs. She began to rub her clit while her other hand grabbed her tits, squeezing and squishing them against herself. The sound of her wet pussy echoed in the otherwise silent room, and watching her breathing heavy while she toyed with herself spurred me into following her command. I began to rub my cock, and after a few strokes, I let out a loud moan. Nadia began to match her breathing with mine, drawing in deep breaths and letting out short, lusty gasps. She leaned over me again and kissed me, her thick, plump lips pushing mine apart and her tongue snaking into my mouth, intertwining with mine. She moaned and gasped into my mouth for a few moments more, before she pulled away and looked at me. “I’m going to get on top of you. You’ve been my good boy and done what I asked, so now I’m going to suck you off while you eat me out. Okay?” I nodded, and laid myself flat and still. Nadia spun herself and climbed over me. her hot breath washed over my cock, and her wet and dripping pussy hung just inches above my face. Another surprise, her clit was pierced, a shiny metal ball on either side of it, the sight of it fully cementing my fetish for piercings. I slid my hands up her legs, over her hips, and grasped her thick ass with my hands, my fingers digging in and holding her tight. Nadia lowered herself, until the pink lips of her pussy were centimeters from my mouth. I let my tongue slide against her clit, drawing a deep, shuddering gasp from her, and she took my cock into her mouth. I began to lick around, playing with her, enjoying the feeling of her trembling lips on my cock, while I grasped and massaged her ass with my hands and toyed her pussy with my tongue. “That’s good baby” Nadia gasped, and she pushed herself against my face “pay more attention to my clit, I’m already turned on, just keep licking me there and I’ll cum.” I began to lick her clit, flicking my tongue back and forth, while her head began to bob up and down, letting my cock slide into her throat. I bore down on her, taking her clit into my mouth and sucking on it, before letting it out and viciously licking. I wanted her to cum before me, and so I picked up the tempo, hoping that I was doing it right for her. Nadia was moaning and whimpering with my cock in her mouth, so much so that she was having a hard time keeping her tempo. I tentatively reached for her head, and began to push lightly, helping her to keep sucking my cock while I continued to lick her, as fast and as hard as I could. Nadia began to shake and shiver, moaning “Fuck, fuck, fuck!” my face was drenched with her, and as she let out one last “Fuck!” she collapsed on me. in a second, Nadia was turned around, kissing me ferociously, so hard that I tasted blood, as she swung her leg over me. I felt my cock slide into her pussy, and Nadia brought her foot up underneath her. she began to ride me, her pussy slamming against me, her tits swaying, and she grabbed my hand, pulling it up to grab and feel her tits. I groped and grasped at her, pulling and pinching her nipples and playing with the rings pierced through them, my other hand grabbing her hip and pulling her against me with every thrust. I could feel her pussy tighten and hold on to me, so tightly that as she rode me, she was pulling my hips up off the bed. As we fucked, she instructed me “Grab my throat and squeeze,” I did so and she adjusted her neck. Through her gasps and moans, she said “the sides, baby, squeeze the side of the neck, not the front” and I adjusted. As soon as I put pressure on her neck like she’d asked, her tempo increased and she started whimpering and moaning even harder. This was all too much for me, and I came, thick, shuddering gasps in time with the pulses of my cum. Nadia slowed, and then stopped. “Did you cum, baby?” she asked, and I nodded. With a start, I realized we hadn’t put on a condom, and I said as much. Nadia smiled, still on top of my, and lifted her leg up. My half hard cock slid out of her, and I saw the lip of a condom on me. “I’m flattered you couldn’t even tell” she said breathily. “I put it on with my mouth. I figured you were too preoccupied to think about it. I told you I was gonna take care of you, hun.” She rolled off of me and laid in the bed. I rolled over, facing her. “Did you… you know…” I asked, and Nadia patted me on the head. “you did very well, baby. Its really hard to make me cum, I usually don’t. but you were close.” I was somewhat disappointed. Nadia seemed tired, but I decided I didn’t want my first time fully fucking a woman, especially one like Nadia, to end with her unsatisfied. “will you teach me how to do that for you?” I asked, and Nadia smiled. “do what for me? make me cum?” I nodded, and she ruffled my hair. “awe, you ARE adorable. I don’t want you to worry baby. Tonight is for you.” I shook my head. “I won’t be satisfied if you aren’t.” Nadia smiled, and whispered “if you really want to try…” and I nodded again. “it might just not happen,” Nadia whispered, “I don’t want you to be disappointed.” As she said this, she had gasped one of my hands and guided it downwards. I felt her clit between my fingers, feverishly warm, with the small metal balls of her clit piercing sliding against my fingertips. I rubbed her clit, and Nadia’s whole body shook. “no baby, that’s too sensitive. I need you to pay attention to this spot.” Nadia guided my fingers lower, and then inside her. she was beginning to breath heavy again, and she mumbled into my ear “make a hook with your fingers.” I did so, and she gasped. “feel that?” she asked breathily, and I nodded. “if you keep hitting that with your fingers, I’ll cum.” I began to slide my fingers in and out, making sure to hook my fingers and hit her Gspot. Her hips swayed a bit, and then she seemed to settle, and just laid there while I fingered her. “Put in another one” Nadia asked, and I slide a third finger into her, surprised that what had felt so tight could accommodate a third finger so easily. A few more moments of Nadia gasping, and she grabbed my face. “you’re doing great baby. Another one.” I slid my fourth finger into her, and she groaned loudly. Her body began to arch, as all four of my fingers slid in and out of her, rubbing her gspot faster and faster. Nadia was shaking so hard that the bed was moving, and she was biting her lip and thrashing her head between gasps and moans. Nadia was getting louder, and her next command was almost a shout, “put it all in, I want it all inside me!” I wasn’t certain what she was asking, so I hesitated, and Nadia slide herself forward, my entire hand sliding up into her. I was completely amazed that she could take my entire hand, but her shaking, screaming orgasm was becoming so frantic that I just kept pushing in and pulling away, until Nadia stopped moving entirely, her legs and tits quivering, and I felt an intense pressure around my hand. “Take it out!” Nadia shouted and I pulled my hand out, and she squirted all over me and the bed. Her scream subsided, and she laid out on the bed, chest rising, but silent. A few moments of silence, and she spoke. “holy fuck. You made me cum. I really didn’t expect that.” I didn’t know what to say, so I just stumbled over some words. “you told me; I just did what you said.” Nadia nodded and blew a breath out of pursed lips. “yea, you’re good at following directions. Sorry if that freaked you out.” I was confused. “if what freaked me out?” Nadia looked at me incredulously. “the whole hand thing. It weirds out some people.” I shrugged again. “guess that’s the benefit of teaching someone? They dunno what to be wierded out by?” I replied, cluelessly. Nadia laughed. “I wanted to do a bunch of other stuff for you… show you some other tricks. But I’m exhausted.” I shrugged and said “There’s always later… Maybe?” Nadia nodded and said “Maybe…” she pecked me on the cheek, and then said “sleep now.”
The next morning, Nadia was gone. I figured I had simply overslept, and she must be outside having a smoke or something, but she was totally gone. She was on my facebook still, I tried to play it cool and didn’t plan to message her for a couple days. Before I messaged her, she posted a status, celebrating her and her boyfriends one-year anniversary. I left it at that, and after a few months of zero contact, chalked it up to a fun experience. I’d shed myself of any pesky virginity and figured I was primed and ready to meet some girls my own age in the coming school year!
I guess now with all the background stories out of the way, I can start writing up and sharing some truly slutty tales of my twenties. There are three that I am thinking of writing about, so I’ll let any of the readers here decide. I can either tell the story of my all male threesome, my very first threesome with the female group tease and my male bestie, or my story of being the free use oral boy for some gals at a college party. Whichever gets more comments will come first. As with all my stories, I encourage interaction; I love talking about my slutty ways, so feel free to comment or message, I’ll do my best to respond!
Source: reddit.com/r/gonewildstories/comments/jqsz9k/how_i_lost_my_virginity_and_was_taught_by_an
wait so u didnt fuck her? that’s a disappointment. well u r so lucky I am happy for u lol