Introduction: This is the actual story of how I lost my virginity. Despite the alcohol, my recollection is exceptionally clear, as it always has been after I drink. By and large, the dialog is actually what was said. The story is a bit long, so I’ve broke it into four parts. Part 1 is an overview and our meeting, 2 further discusses our drunken courtship, 3 finally leads us to bed, and 4 is my redemption. Enjoy and please feel free to comment and I’ll feel free to consider or ignore it.
Overview of Parts 1, 2, & 3: I’m an 18 yr old male, sexually inexperienced, and just made it to New Orleans. While enjoying the liberal alcohol policy of the city with my friend, I met Lisa from Indianapolis at a local bar. She is 46 and a recent divorcee who is trying to forget her marriage with a trip to New Orleans to hang out with her friend. We have been petting and teasing each other throughout the night. After some serious exploring of her body, her friends gave me a ride to enjoy the remainder of the night with Lisa. Our initial sex was fast, furious, and neither started or ended like I had always envisioned.
Opening my eyes, I scanned my surroundings. Where am I? This doesn’t look like the hotel. The clock glowed 5:40 am. I rolled over rubbing my eyes. Holy shit I murmured as I saw a woman laying beside me with her back to me. Everything came back to me. Everything. I must have passed out after my last declaration of defeat. The exhaustion of traveling, dancing, and simply staying up so long had caught up with me during sex. Sure, I was somewhat drunk, but not all that much which was confirmed by the fact that I was awake after only a couple of hours of sleep and although tired, I wasn’t feeling the affects of alcohol anymore. Well, I’ll be damned if I’m going down in flames like that.
As I slid my body towards Lisa, I lifted the covers allowing my first unobstructed view of her ass. Those curves are just what I remembered and her ass cheeks were nice and firm. I’ll be damned I thought to myself. She’s really good look’n, it wasn’t just the alcohol. I wormed my way over to spoon her. Her breathing was soft. Her warmth felt good in the air conditioned room. I want more.
My hand slowly reached around her and found her right breast. As I cupped it in my hand, I felt her nipple harden between my fingers. I kneaded her nipple between my fingers enjoying the feeling of a breast in my hand; her breathing began to pick up. I could feel my cock stiffen and began pressing between her ass cheeks. I stretched my neck so I could start nibbling on her earlobe. Her breathing was getting heavier and she started to squirm a little.
“Mmm. I like that.” she whispered.
I didn’t say a word. I just kept nibbling and kneading, but my hips started to involuntarily gyrate causing my cock to inch its way down her crack and slip between her legs. I could feel the heat from her pussy against my head and shaft.
She began to stretch, squeezing my cock between her legs. Her head turned, eyes fluttering as she worked the sleepiness out of her eyes, and she smiled. “Ready for more, huh?”
Again, without saying a word, I turned her over and began sucking on her nipples. At first, Lisa was quiet as she continued to wake up. Her nipples felt so hard but rubbery. I worked my mouth back and forth between each nipple while lowering my cock against her pubic mound. The feeling of her soft pubes against my cock felt so good as I stroked the underside of my cock against her mound.
By this point, Lisa was fully awake. Her hips were matching my stroking and her nails started digging into my back. I released her nipple from my lip-grasp and slowly kissed my way down towards her womanhood. As I neared her bellybutton, she giggled a little and began pushing my head further south.
I kissed the top of her public hair strip and sucked in a little skin with it. With my chin now rubbing against her clit, she let out a sigh. Placing my hands on the back of her legs just below the curve of her ass, I started exploring the area between her pussy and asshole. Her hips started slowly grinding into me and I could once again smell her musty juices. My tongue stretched out to lap up the first bit of juices that had started pooling at the bottom of her pussy. As I continued lapping at her pussy, I allowed my hand to rest against her mound and my thumb start slow circular motions around her clit. My other hand rubbed her asshole while a finger slipped into her pussy allowing my tongue to work in tandem with my other hand on her clit.
“Oh, yes.” she hissed.
My assault on her clit, pussy, and asshole began to quicken. Her hips made circular motions, pushing against my face and hands. She continued to make sounds of exhilaration, but was unable to compose an actual word. As before, her ass shot up off the bed, everything stiffing, her hands slamming onto the bed grabbing handfuls of sheets, and a last gasp of air rushing into her lungs.
“Christ!” she grimaced through clinched teeth.
With that, her body seemed to levitate off the bed as convulsive shock waves shook her body. Again, a rush of fluid coated my hand and mouth. I tried to capture her juices, but with my hand in the way warm liquid dripped from my wrist and chin. My hands stopped their assault while I cleaned up her cum with my tongue. Her body fell to the bed and I retracted my hands, allowing my breath to cool her clit and make her pubic hair sway in the breeze.
I was determined to savor every moment of my cock entering her pussy. Lisa was still recovering from my handiwork, but her legs spread as I positioned myself. My inexperience struck again. Instead of guiding myself into her, I allowed my cock to dangle freely and tried to take a stable at her. My aim was a little high, so I glanced off her opening, spreading her lips, and slid up across her clit.
“Goddamn!” she shouted as her body suddenly jerked.
“You’ve got be careful honey. I’m too sensitive down there still.”
“I’m sorry … I …”
Hearing my disappointment at myself, she smiled and wrapped her hand around my cock.
“Don’t worry. Let me guide that to were it belongs.”
With that, she pushed my cock down a little and I felt my head start to spread her open. Without the alcohol, I could finally absorb all the sensations my cock was feeling. She was warm, damp, and smooth feeling around my cock.
“You feel tight.” I said factually not really thinking about the ramifications of the statement.
“You sound surprised.”
“No, I’ve just never. Well, I’ve never had sex before. Aside from earlier.”
“You were a virgin?”
“Were.” I said as I developed a slow rhythm feeling her muscles contracting around me each time I entered her. Her smile broadened as she reveled in the delight of taking my virginity and having a very young man eagerly desiring her. Our rhythm and breathing increased as my balls began making a slapping noise against her ass. Within a matter of minutes sweat was dripping from my face and we were both grunting.
“Cum in me. I wanna feel your cum in me.”
Between hearing a woman saying such a thing to me and the new sensations grasping my cock, my cock twitched. The tightening I felt in my balls when I masturbated suddenly came over me and in less than a stroke I could feel my cum sprinting its way up my shaft. Instinctively I stopped my rhythm and slammed my cock as far as I could into her pussy. My toes curled as waive after of waive of spasms rocked my cock and my cum filled her pussy. I remained in my yoga cum pose until the only spasms I felt were her pussy trying to pull more cum from my drained balls. Looking down at Lisa, her eyes were nearly closed her smile was so big. I fell to her side finally drawing air into my lungs.
“It must be late in the morning” I thought to myself as my eyes adjusted to the light. I looked towards the clock, 8:15 am. After that last session, I exhausted myself and I suppose I passed out again. Her arm was wrapped around me, leg across mine, and she was exhaling against my neck. As I starting running my fingers through her hair, I felt my cock starting to grow again. I want more. I let my other hand start to roam about her shoulders and chest. Lisa started stirring and her eyes slowly opened up again with a smile.
“Are you serious? Again?” she chuckled.
“I reckon I can’t get enough.” I said as my hand once again found her breast, my fingers encircling her stiffening nipple.
“I’ve forgotten what it’s like. I haven’t had sex more than once in a night in years.”
Rolling into each other, our lips met and our tongues intertwined in a now familiar dance. Her hand started rubbing my chest, running her fingers through the fair amount of chest hair I had already developed. I was already hard and her thigh was rubbing my cock. Slowly, tongues still dancing, she rolled over on top of me. Lowering her ass, she guided my cock to her entrance. I could feel the heat, but not the dampness I had become accustomed to feeling. She slowly pushed back allowing my head in and then started grinding her clit into my pubic bone. After a few grinds, more kissing, and more groping of her tits, I felt the wetness return and less resistance as she backed herself further down my shaft.
Once my cock was fully engulfed in her womanhood, she raised herself off me. I was struck by the beauty I could only now fully see in the morning’s light. Her breasts were not stiff, but their battle against gravity was going well. Her nipples looked like large erasers on top of dark silver dollars. I could make out the bottom of her ribcage as her body narrowed towards her waist and flared dramatically at her hips that were draped around my hips. The top of her trimmed rectangle was visible while the remainder was tangled amongst my public hairs. The contrast of her hairs and mine was visible and exciting.
I reached out to grabbing her hips while she developed her rhythm. I could feel my balls squishing against her ass cheeks with each downward thrust she gave me. Her walls kept flexing against my cock each time she lowered herself on me and released slowly with each withdrawal.
“You keep that up and I’ll be cumming in no time.” I protested.
She just gave me a devilish grin while she bit her lower lip, closed her eyes, and returned to her task. I moved one of my hands to the front of her pussy and found her button. It was difficult to keep my thumb against her clit, but finally learned to push my palm against her pubes, relax my arm, and allow it to follow her motions.
“Now you’re going to make me cum in no time.” she sighed with a toothy grin.
I wrapped my arms around her back and pulled her towards me. Giving her a kiss, I twisted us over so I was once again on top without dismounting her from my cock. I leaned back giving me a view of my cock going in and out of her. I slowed my pace so I could take the view in longer. My cock would slide in and out, glistening from her juices with a little white cream sticking to our pubes.
“Enjoying the view?” she teased.
With that I leaned forward again, kissed her, and started pumping her with all my might.
“Yeah, fuck me. Harder!”
I was starting to tire as I pounded as hard and fast as I could. Her nails were digging into my back, my balls actually started to hurt a little from slapping against her ass so hard. She wasn’t gripping my cock anymore causing it to glide easily in her well lubricated hole. Her breathing was quick and labored while she grunted from the force of my thrusts.
“Fuck me harder!”
I could feel my cum brewing. Her walls suddenly contracted around my cock and she let out a low, long growl. Just as I felt my first contraction, I sat up pulling my cock out. My first shot of cum arced up and on her belly while the remaining jets became entangled in her pubes. I continued to slowly slide my still twitching cock against her pussy. Her hands slid down and she started rubbing my cum into her pubes and stomach, taking a little on her finger and sliding it between her lips. I had never witnessed anything more erotic.
“Damn, I love this.” I said as I fell to her side in a heaping sweat of a mess.
We talked for a few minutes, but I was once again out of energy and found myself dozing off. When I awoke, I was alone, but I heard the shower turning off. As I lay there, I couldn’t believe that my cock was growing again. By the time Lisa returned, I was ready for another round.
“I’m ready again” I said proudly jerking my head towards the tent I made in the covers.
“I just got cleaned up. You need to as well and I’ve got to catch a flight. Do you want to call your friend to pick you up?”
Realizing the fun was over, I also realized I hadn’t thought things through as well as I gave myself credit for. I didn’t know where I was other than in a suburb of New Orleans. I didn’t have my truck. I didn’t know the name of the hotel I was staying at and even if I did, I had the keys to my truck so my friend couldn’t drive out to pick me up.
“Shit. I don’t even know where my hotel is. How much you figure a cab is from here to the French Quarter?”
“Fifty or sixty bucks.”
“I’m screwed. I don’t have but a couple of dollars on me.”
“Don’t worry, we’ll take you back and I’ll even buy you some lunch.”
With that, she leaned over, gave me a kiss and thanked me. I headed for the shower to feel a little normal again. Her friends weren’t thrilled with having to take Lisa’s boy-toy back, but they were accommodating. We ended up on a fairy and Lisa and I were leaning against the railing enjoying the warm breeze against our skins.
“I hope you enjoyed last night.” I said as I wrapped my arm around her waist and leaned in for a kiss. Lisa’s eyes darted around and she gave me a quick, platonic peck on the lips. It was fun, but I guess it’s over, I thought to myself.
I inhaled a wonderful bowl of jambalaya while everyone conversed. After I finished my last bite, I could feel it was time to leave. I thanked Lisa and her friends for their generosity as I excused myself and headed towards the doors.
I turned to see Lisa quickly walking towards me. Her arms wrapped around my neck and she planted her lips on me, slipping her tongue in my mouth one last time. Inhaling deeply, she said “You’re so cute. I really enjoyed you. Have a safe trip home.” Without waiting for a response, she released me and hurriedly returned to her table.
I worked my way back to somewhat familiar surroundings reflecting on my good fortune the entire way back. As I approached my hotel, I suddenly felt ill. Aside from trying to figure out how to get back to my hotel a few hours ago, I hadn’t thought about my friend since early last night when I blew him off. It’s going to be long drive back home. I’m such a shit … but not a virgin shit anymore I thought to myself as I smiled again.