I waited all day for 5:00 to finally arrive. It was Friday, which meant that I’d be taking the train to spend the weekend with Pete. I had a little bag all packed and waiting, under my desk. I made a mental note to stop out over the weekend and buy some toiletries to leave at his apartment; he’d already asked me why I hadn’t yet, seeing as how I’d spent every weekend for the last six weeks with him, not to mention another two nights per week.
I had spent so much of my life feeling alone and unloved. I was in my late 20's and had never had a serious boyfriend before. I’d gone on dates but had never found anyone who wanted me just the way I was. I’d weighed a lot more in the past; since college I’d lost nearly 100 pounds, in fact. Now I was curvy in all the right places, with 36C breasts, a small waist and thick hips and ass; still, in the past it had seemed as though I was only finding guys who were interested in supermodel-skinny girls.
When I met Pete, everything I’d ever thought about men was turned on its head. From the moment we laid eyes on each other, I knew he wanted me. We’d met online, by accident. We started writing emails to each other as friends, and I had to admit that he was interesting and funny and intelligent…everything I wanted. Over the course of a couple of months, we grew closer and closer, and I could tell that he had checked out my social media profiles and liked what he saw. He’d called me “beautiful” and “cute”; it was unlike anything I’d ever experienced, for sure.
Finally, the night we first met in person, I knew that he was mine if I wanted him. I was wearing a low-cut tee shirt and denim jacket, with leggings and cowboy boots. He complimented my boots, but I could tell from the way he kept averting his eyes whenever I’d look at him that he was interested in my cleavage and the way my leggings showed off my butt. As for me, I was impressed with his strong arms and make it a point to “investigate” the tattoos on both biceps. I just wanted to feel his muscles. He had worked in a warehouse for years before becoming an IT manager, and he was still strong. I found his shaved head incredibly sexy; in fact, he had a masculinity that radiated from him and attracted me to him.
Most of all, he was a gentleman. By the end of the night, I was certain that he wouldn’t kiss me unless I made the first move. It’s not that there wasn’t a mutual attraction. Like I said, he’d been flirting with me for months and had been ogling me when he thought I wasn’t looking all night. Still, he was waiting for my signal. So I gave him a signal, all right: I invited him to walk me to my apartment door and, once we reached the vestibule, wrapped my arms around his neck and kissed him. He kissed me back eagerly, his tongue dancing with mine, but he didn’t put his hands anywhere I didn’t first guide them - including when it came to kneading my firm breasts, encased in a black lace bra.
He knew that I was a virgin.
I had revealed my secret a few weeks earlier in an email; I had just watched The 40 Year Old Virgin for the first time with my roommate, and I was telling Pete via email how much I’d enjoyed it. Then, I decided to drop the bomb: I was a 26-year-old virgin.
He told me he respected the fact that I had waited for somebody I cared about, and that he sometimes regretted his experiences and wished he could start over. He’d lived with a few different women before he met me, and all of those relationships had ended poorly. Still, I could tell from the way he used his hands as we made out that he had learned a thing or two.
This is why he was so hesitant with me; he didn’t want to cross a line with which I wasn’t comfortable. In reality, I had wanted even more. I could feel his stiff cock through his jeans, rubbing the thin material of my leggings. I wanted more…but waited.
One thing was settled that night, though: He asked me, in between make-out sessions on my sofa, if I wanted a boyfriend. Of course, I did.
Two weeks later we slept together for the first time. The whole night was magical. I’d taken the hour-long train ride to his apartment, and he had me wait outside for a minute while he lit candles around the place. A bouquet of red roses was waiting on the coffee table. I had been so nervous when I first got there, but I realized he’d never be anything but good to me.
Later that night, we made out again in bed. I was wearing a tank top and boy shorts. My heart was pounding both from nerves and from what he was doing to me. My nipples stood up, hard and sensitive, against the thin cotton top. He gently flicked them with his thumb, sending bolts of electricity straight to my crotch, which was getting wetter steadily with every touch.
He rolled me over onto my back. He started tonguing my nipples through my shirt, leaving me gasping and whimpering. The heat between my legs was growing more intense - it almost hurt, he had me so turned on. My hands roamed the back of his head, his shoulders, his back. I dug my nails into his ass cheeks, pulling him closer to me. I could feel that bulge again, pressing against the fabric of my underwear. I touched it with my fingertips, making him throw his head back and moan loudly.
“Fuck,” he whispered. I did it again. And again. Soon I was rubbing him through his shorts, and he was thrusting his cock against my hand. Eventually, he couldn’t take it anymore, and I slowly pulled his shorts down. His 7” cock sprang from its confines and made me gasp.
Still he hovered over me. I knew he was waiting for my move. So I sat up just enough to slide my tank over my head, then laid back down.
This was further than I’d ever gone, and I felt exposed and a little scared.
But I didn’t need to be scared. He sat back on his calves and looked down at me, taking in the whole picture. “What do I do with all this beauty?” he whispered.
He knew what to do, believe me. His hands slowly roamed from the bottoms of my feet to my ankles…up my calves, behind my knees…over my thighs…
I arched my back in anticipation.
His hands continued over my stomach, then inched their way over the swells of my breasts. I cried out, twisting the sheets in my fists. “More, please,” I panted. “Suck them. Suck my tits, please.”
I could tell he was shocked, and his cock twitched at my words. I was too far gone to care. I needed his mouth on me. So he dove onto my breasts, licking and sucking first one, then the other. He went back and forth, slowly dragging his tongue in circles, then flicking it back and forth rapidly. I almost screamed.
Meanwhile, one of his hands had found its way between my legs and began to rub my mound. “Somebody’s excited,” he whispered, and I knew he felt the wetness that had soaked through the fabric. My hips bucked and flexed, riding his hand as he drove me further and further toward my climax.
“Can I touch you?” he whispered.
“Please,” I begged. “Touch my pussy. Please.”
He crawled between my legs then slowly, gently raised my legs until my ankles were resting on his shoulders. I lifted my hips, and he pulled off my underwear. We were both naked, our bodies glowing in the light from the candles he’d lit in his room.
He started kissing his way up my leg, starting at the insides of my ankles, pausing to swirl his tongue behind my knee. Then he started up my inner thigh, and every kiss drove me crazier as he got closer to the center of the heat.
He reached the apex of my thighs and grinned at me before he swiped his tongue along one of my lips, then the other. I moaned his name, over and over, as he teased me with his tongue. Every time I thought he was going to dip his tongue into my wetness, he pulled back. He loved driving me crazy.
“Can I eat you?” he asked.
“Yes. Please, eat my pussy,” I whispered, panting, begging for more.
He slowly slipped his tongue between my lips, dipping into the hot wetness. Then he touched it, so gently, against my clit. I gasped, again twisting the sheets, gripping his head, clawing his shoulders. He began to lick that spot, over and over, alternating between flicks and laps with his tongue.
“Mmmm baby, that feels so good,” I moaned. My head twisted from side to side as he assaulted my clit with his skilled tongue. I began grinding my hips into his face, so close to cumming. I heard him moan in approval, and the vibration from his mouth finally sent me over the edge. I screamed and shook.
He crawled up beside me and held me as I trembled, my first orgasm with another person leaving me feeling so vulnerable. He kissed me, gently, on my neck and shoulders. His hands gently stroked my back and butt. I felt happily safe…and, soon, turned on all over again as his hands worked their magic.
I whimpered against his shoulder, and his fingers found a magical spot at the very bottom of my back, where he led to the cleft between my ass cheeks. Every time his fingers brushed that spot I felt like I’d break into a million pieces. I gripped his shoulders and gasped and cried out. I felt the flood gush between my legs once again. As he touched me, he sucked and licked my neck. I was so close to cumming all over again. Only this time, I wanted him inside me.
“Please, make love to me,” I asked him. He asked if I was sure, and I nodded my head. I needed to be with him, right then and there.
He rolled me onto my back again, and I laid there as he rolled a condom over his thick cock. I was practically salivating. I knew it wouldn’t hurt; I’d been using vibrators and dildos for years to fuck myself silly.
He leaned down, his hands on the other side of my head. “You sure?” he asked again, and I kissed him. I then helped guide him into my hot, wet hole.
I gasped when I felt the head pass through, and moaned from deep in my throat as he slowly pushed forward. I felt so filled up; this was nothing like my solo play. There was nothing compared to a real, hot, throbbing cock inside me. And a dildo couldn’t moan; his moan of pleasure, so like my own, sent shivers through me.
This is it, I thought. I’m not a virgin anymore.
He pulled back, then pushed forward. Back, then forward. Again and again. We found our rhythm together, moving against each other. I urged him on - more, please, more, more. Harder. Faster. Yes. Please.
He sat up, taking my hips in his hands. I placed my feet on the bed for leverage as he pounding his cock into my pussy over and over. My tits bounced up and down as he thrust in and out of me, and before long I could feel another orgasm coming on.
“Oh fuck!” I screamed, “Oh fuck oh fuck I’m coming ohmygod….OOOOOOOHHHHHH!” I could feel my pussy spasming around his thrusting cock, still slamming into me over and over. Soon his moans got louder, the thrusts even harder. “Ohhhhhh FUCK I’m CUMMING!” he shouted, then threw his head back and shuddered. I could see the veins standing out on his neck as he thrust one, two more times.
I remembered that first time, and all the times we’d had since then, on the train ride to his apartment that Friday night. For somebody who was so respectful and worried about offending or making me uncomfortable before we’d started having sex, he turned out to be a very imaginative lover.
One night I asked him if there was anything in particular he liked. We had just gotten done having sex for the second time that night; I remember when sucking and fucking until 2 am was the norm, in those early days. He blushed, and I could tell he was hesitant to share with me.
The following day, when I got home from work, I found an email from him. In it was a kinky story he’d written, based on a fantasy he had about getting home from work to find me waiting for him in knee-high boots, thigh-high stockings with garters, bra, and panties. In the story, he blindfolded me with his necktie and played with me. It was the hottest thing I’d ever read, and so sexy the way he described getting me off with his fingers, his tongue and finally, his thick cock. He described riding me while I still wore my boots.
I knew he thought my boots were sexy; one night only a week earlier we’d gotten home from grocery shopping after work, me in my high-heeled boots, and a dress, with a trench coat on top. He managed to wait until we put away the perishables before he bent me over the kitchen counter and pushed my dress up around my waist, then licked his way up the backs of both bare thighs and over my full, round ass cheeks. Then he pulled down my thong panties in one swift motion and fingered me, right then and there, until I screamed and squirted all over his fingers. He pushed me down on all fours so he could fuck me from behind. I hadn’t even taken off my coat but happily complied, grunting and moaning as he pounded his cock into my pussy from behind and rubbed my clit again until I screamed his name.
With his story in mind and the memory of that encounter in the kitchen, I knew what I wanted to do that weekend. I was so horny by the time I got off the train that I greeted him by jumping into his car, then promptly sticking my tongue down his throat and rubbing his bulge until he had to beg me to stop before he came in his pants. I knew I’d set the tone for the weekend.
We went to dinner, as we normally would on a Friday night, then got in the car for the 10-minute drive to his apartment.
I was wearing a wrap dress I knew he loved. It came down low in the front, revealing my full cleavage. I had deliberately opened it a little after work; no way I’d work with half my tits hanging out. All throughout dinner I’d sat with my arms crossed, leaning over the table. My tits, in their push-up bra, were on full display. I knew he liked what he saw, as he stared down my dress.
Meanwhile, I was wearing stockings and heels but not just any stockings. What he didn’t know was that I’d bought thigh-high stockings and a garter belt, just for him. When I got into the car after dinner, I pulled my dress up a bit so he could see the tops of my stockings.
I heard his sharp intake of breath.
“Do you like what you see?” I asked, slowly pulling my dress up in the dark parking lot so he could get the full view of my smooth, stockinged thighs and the garters that held them up. I glanced down at his crotch and saw that he was already fully hard.
“Maybe you should take me home so we can have fun with these,” I suggested. So he started driving…only his right hand rested on my thigh, rubbing up and down. It was getting me excited, and immediately I could feel myself getting wet. I couldn’t believe this - we were still in the car, driving down a busy road, and he had his hand up my dress.
I closed my eyes and breathed faster as his hand crept further up until he cupped my mound through my panties. I was wearing a thong again, which he easily moved aside to get better access to my hot, wet pussy.
“Pete!” I gasped, shocked that he would do this out in public. Anyone in a passing truck or bus could have pulled up beside us and seen what was happening. But he didn’t stop; he didn’t even look at me or say a word. He simply dipped his fingers into my wet slit and started strumming my swollen, throbbing clit. I lowered the back of my seat ever so slightly so I could spread my legs further and give him better access.
The fact that we were in a moving car made it even more exciting, and by the time we pulled up in front of the apartment I was coming down from my second orgasm. I didn’t think I could move, my legs were shaking so hard.
“I need you,” he whispered in a raspy voice, and I knew he was throbbing. Getting me off always turned him on; he was always hard as a rock after he made me cum.
I pulled myself together enough to get out of the car. We hurried to the door, behind which was a series of stairs that led to his second-floor apartment. We got inside the front door and shut it behind us. He then spun around and pinned me against the wall. Before I knew it, the front of my dress was pulled open, and my bra pulled down to expose my tits to his hungry mouth. One hand was on my right tit while his mouth was on the left. His other hand was back between my legs, once again feeling around greedily, searching for the source of the wetness that soaked my panties. He found it, and started pumping two fingers in and out. I put one foot up on the stairs to spread my legs further, and he added a third finger. He fucked me with his fingers, and I struggled not to scream.
“Oh, Pete, oh baby that feels so fucking good,” I whispered, urging him on. “I fucking love it, don’t stop baby, make me cum again, baby.” He slammed his fingers in, and out so hard my tits bounced up and down. He kept licking and sucking first one, then the other, as I begged for more.
Finally, my third orgasm swept over me, and I had to hang on to him to stay upright. My knees trembled as I came down from it. I bit his neck and earlobe, knowing how much he needed the release.
I fell to my knees right there and yanked his pants down around his ankles. His straining, throbbing cock was dripping pre-cum, which I licked from around the tip. He groaned his hands in my hair. I licked, gently, all around the swollen, purple head while gently playing with his balls. I knew just how he liked it, and the way his head was thrown back and his pulse pounded in his throat told me that I was doing a good job.
I dragged my tongue gently but firmly from the base of his cock all the way to the sensitive spot beneath the head. He had explained to me that this area was like a clit to him, so I paid special attention to it. I flicked my tongue over it, just as he did to my clit when he was eating me out. He gasped. “Yeah, baby, put it in your mouth. Suck on my cock,” he ordered.
“Only if you fuck my mouth,” I told him. I loved feeling him use me like that, just pounding his cock in and out of my mouth. Here I was, kneeling in his vestibule with my dress open and my tits hanging out. I wanted him to use me like a whore.
So he took his cock in his hand and forced it past my closed lips and into my mouth. “Mmmmmmm,” I moaned. He then took the back of my head in both hands and started pulling and pushing on my head, thrusting in and out of my mouth. I loved this and was already starting to get hot again. I was practically dripping on the floor.
I sucked his cock as he continued to thrust until finally I could feel his thrusts getting stronger and more deliberate, and heard his moans getting louder and stronger. I knew he was about to cum, so I got ready to take his load in my mouth.
Then I tasted it, as it shot out of his cock into my throat so hard I thought it would blow the back of my head off. Once, twice, three times he shot into my mouth. I quickly swallowed, then waited until he was finished to swallow again.
We were both so drained after that; we didn’t do much else but go to bed and pass out in each other’s arms. The following morning he went to work; he always worked til noon on Saturdays. Before he left, he woke me with kisses on my neck and shoulders but then let me go back to sleep.
After I had waked up for the second time that morning, I got myself ready for that afternoon’s fun. I showered carefully, shaving perfectly smooth from the waist down. We both preferred it that way. I cleaned myself carefully, too, knowing that his mouth and hands would be all over me soon enough.
Finally, I dressed. I knew from other conversations we’d had that he found vinyl sexy; with that in mind, I had purchased a black vinyl bra and panty set online. The bra held my firm breasts up high and enhanced my deep cleavage. The panties were skimpy, barely covering my smooth mound and leaving my ass exposed. Over that I wore a vinyl garter belt which held up black fishnet stockings. Black vinyl boots came just up to my knees and laced all the way up the front. Matching vinyl gloves went up to my elbows and completed the look.
I gazed at myself in the mirror. I couldn’t help admitting that I felt sort of powerful like this; I had never imagined wearing this sort of outfit, but now that it was on I liked it. And just imagining what he’d do to me when he saw it was enough to make the effort worthwhile.
Before long I heard his car pull up in the driveway. I busied myself in the kitchen, emptying the dishwasher in my outfit as a little joke. I bent down with my ass sticking up toward the door to the apartment.
“Did you have a good morning…?” I heard as he entered the apartment.
Slowly I straightened up and turned around. His jaw was practically on the floor.
“Like what you see?” I asked. He nodded, hard. Speaking of hard, his pants were already bulging.
He walked over to where I stood. “You know, you didn’t have to do this,” he murmured. “That was just a fantasy I had. It wasn’t instructional.”
I smiled. “I love you, and I want to be your fantasy. I want to fulfill every need you ever have,” I told him, and I meant every word.
He ran his fingers lightly over my cleavage, inspecting the bra I wore. Goosebumps rose all over my skin at his touch. His fingers lightly trailed down my sides, to the garter belt I wore. He slowly dropped to his knees and ran his hands over my stockings, down to my boots.
“Turn around,” he commanded. I did so, and his hands went back up my legs to my ass, where they hovered, and then up my back to my neck. He stood, and wrapped his arms around me to cup my tits in his hands.
“Let’s go into the bedroom,” he whispered before licking all along the back of my neck and biting my earlobe. My knees were weak, my clit already throbbing from his touch.
I stood in front of him as he quickly undressed. His cock stood tall, and he stroked himself just watching me stand there. “I could jerk off right now, just looking at you,” he said. I pouted, and he laughed. “Oh, did you hope I’d do things to you?” I nodded, eagerly.
“What did you hope I’d do?” he asked.
“I wanted you to lick my pussy, and then fuck me with my boots over your shoulders,” I told him. He stroked faster.
“Get on the bed on your hands and knees,” he ordered. I did, and he stood behind me, admiring my ass. “God that’s sexy,” he said. His hands roamed all over my round ass, then dipped between my legs. I moaned and threw my head back. I spread my knees further apart. He bent behind me and pulled the skimpy crotch of my panties to the side, then began licking my slit. I whimpered as he swirled his tongue around and lapped up my juices. He flicked his tongue over my clit, and I arched my back, and then his tongue swirled around my hot, wet hole and I almost collapsed from the sensation.
“I don’t want you to cum yet,” he whispered, then nudged me, guiding me to roll over onto my back until I was laying across the bed. He walked around the other side of the bed until he was standing over my head.
“Suck my dick,” he ordered. My head was hanging upside down off the side of the bed, his cock and balls above my face. I took his thick cock into my mouth and sucked as he slowly thrust.
“I love seeing you like this, dressed up like a slut, watching you suck my cock,” he whispered, his hands roaming over my tits and chest as he thrust into my eager mouth. His words made me even wetter, and I tingled all over. My gloved hands roamed over his ass, pulling him closer to me, commanding him to thrust harder. He did, and I struggled not to gag on his delicious cock as it rammed into my throat.
He bent down and began fingering me as I sucked, then started licking my pussy. Both of us moaned as we 69’d together, me underneath with his cock pumping into my mouth, him on top with his tongue flittering over my swollen clit.
Pretty soon I couldn’t take it anymore, and I started grinding my hips against him. He knew I was getting close, so he slid two fingers into my waiting hole. I cried out, his cock still in my mouth. My moans only spurred him on, and he stopped thrusting into me to focus on my pleasure. I gripped his back with my hands and rode his face until my climax washed over me.
He pulled out of my mouth, and I shuddered and moaned as the sensations traveled through me. He waited for me to finish recovering, then walked around until he was at my feet.
He grabbed my ankles and pulled, until my ass was at the edge of the bed. He unhooked my garters, then slid my panties down over my boots in one fluid motion. Without saying a word, he slid the head of his cock through my juices a few times, then lined up the head with my hot and ready hole. He pushed into me, hard. I shuddered again, gasping and throwing my head to the side at that first blissful sensation.
He slid in and out, smoothly, his cock already slick with the juices that pooled out of me. “You’re crazy wet,” he muttered. “So hot, and tight, and wet.”
“Fuck my tight pussy, baby,” I moaned, and he thrust so hard his balls slapped against my ass.
He picked up my legs and rested them on his shoulders, my boots sticking up in the air. It was insanely sexy watching him fuck me with his hands roaming over the vinyl and fishnet. He closed his eyes and threw his head back, lost in sensation as he pumped his cock in and out of my pussy. I met him thrust for thrust, grunting every time I felt him slam into me.
He pushed one leg to the side, keeping the other standing straight up. It gave him an even better angle, and he thrust deeper and deeper into me. He reached down and started playing with my sensitive clit as my hands pinched and squeezed my nipples.
“That’s right, baby,” he whispered as he pumped in and out me, the sweat standing out on his skin. “Play with your tits. Let me watch you.” I pulled off my gloves so I could feel myself more. I loved the way my tits felt in my hands.
Then I reached down and replaced his hand on my clit with my own. He watched as I rubbed my clit while he pounded my pussy. I started moaning louder, loving that he was watching me and loving that he loved seeing me get myself off.
“Oh! Oh! Oh!” I cried out as he slammed harder and faster into me. I was going to cum again, and it was going to be huge. I closed my eyes and arched my back, my fingers flying over my clit, his cock pounding me into oblivion. “Yes! Yes! Fuck me! Oh my god, yeeeeeeeeesssss!” I screamed as my climax slammed into me like a tsunami. My pussy tightened around his hot cock, and that threw him over the edge, too.
He pulled out, quickly, and squirted his cum all over my tits. He had never cum on me before and didn’t have to since I was now on the pill. But I didn’t mind; I liked it. I watched as ropes of cum spilled onto my skin, and saw the sheer pleasure on his face as he came.
After that day, there were plenty more dress-up events. We experimented whenever we could - tying each other to the bed, blindfolding each other, using vibrators (he especially loved when I ran it up and down his cock as he was tied up). I bought plenty of new outfits, with corsets and vinyl skirts and crotchless panties.
Ten years later I still have a drawer with all of those items in it. I don’t wear them as much as I once did - marriage and careers will do that - but every so often I look in that drawer and remember all of the fun we used to have back when he was teaching a naïve young virgin how to fuck.