After high school I worked odd jobs for two years saving for college. I lived at home until I was 22, and then for the last few years of school I had enough money to move into a small house near campus with two friends. Living away from home was supposed to help my social life, but in reality I still had trouble meeting women and getting dates. Let alone getting laid. My roommates had much more success in that department. Most weekends at least one of them had a woman over for the night, and sometimes during week day evenings as well. They rarely stayed with one woman long mostly preferring to play the field and one night stands.

My sex life consisted of looking at porn online and masterbating. I have always had a fetish for women’s legs, nylons, pantyhose, garter belts and high heels. Any one of those would get my attention up. So images or video of women in nylons were my normal inspiration. While one or both of my roommates might be fucking in their rooms I would put on headphones and listen to music or play video games. One night while in the kitchen making myself something to eat my roommate John came home with a very pretty woman. She was about 5 ft. 8 in. tall in her high heels. She wore a tight fitting black skirt, white blouse and black high heel pumps. She spoke with a charming and kind of sexy British accent. He introduced her to me as Helen. He offered her something to drink. We stood around in the kitchen talking while I cooked and they drank for a few minutes. I told them I would be done in a minute and leave them alone so they could sit in the living room in private.

Helen looked me in the eyes and said, “That’s ok, we’ll be going into his bedroom as soon as I finish my drink”. I assumed that is where they would end up, but I was surprised at her bluntness towards me. I liked her direct approach of saying what was on her mind. She finished her drink and they walked into his room. I stared at her legs as she walked away from me. I grew hard just looking at her. If she had been wearing nylons with seams up the back I probably would’ve cum right there in the kitchen.

Since they were in his room I stayed in the living room to watch TV and eat. After about two minutes Helen walked out of the bedroom and over to the kitchen. She had left her purse on the counter. I couldn’t help but glance over for another look at those legs. She caught me looking so I tried to say something to seem less obvious so I blurted out “Is everything ok? can I get you anything?” trying to sound like I’d get her more wine, but it sounded more out of place and weird. She just smiled at me and said, “No thanks love, but if I do need anything I’ll come find you”. I didn’t know how to respond to that. I just stared at her realizing the top few buttons of her blouse were now undone and there was a good amount of cleavage from what were probably “C” cup breasts. Probably undone while John was fondling her.

I didn’t know if she was just trying to shock me (probably), was flirting with me (highly unlikely), or might have a wild and kinky side (you never know). I watched her walk into his room again and turn to look at me as she closed the door with a grin on her face. I went to my room to play some video games and try not to think about how I was still a virgin, and how John was having sex with a beautiful woman with fantastic legs that he probably didn’t appreciate. Before I could get the headphones on I heard her clearly say “First you need to lick my pussy before I’ll consider sucking your dick”. That was it for me. No time for video games. I was going to sync the headset up to the computer to look at porn videos and stroke myself. While the computer booted up I clearly heard her moaning very loudly.

I started stroking myself while listening. I felt like a pervert listening to John and Helen, but I was so hard and turned on I just kept running my hand up and down my 6 inch cock. I quickly went to my dresser and pulled out a black thigh high stocking I had bought. I imagined it was Helen’s and I wrapped it around my dick and kept stroking with it. It felt soft and smooth against my rigid cock and I savored the feeling of it. I got closer to the wall to listen to them. Helen said “Lay on the bed so I can sit on your face while I suck you.” That triggered my orgasm right then and there. I hoped they didn’t hear me grunt or moan as I came. Shooting rope after rope of cum uncontrollably all over the wall and floor. I jerked myself off again as I listened to her moaning while they fucked. They didn’t say much, but didn’t need too for my arousal. Helens loud moaning was more than enough for me especially with the image of her legs in that skirt and those heels.

I had cum twice in 10 minutes just from listening to them fuck. I sat on the bed to relax and wait for my erection to diminish so I could get a drink of water to cool off. I could still hear her moaning which wasn’t helping matters. I was still not fully flaccid yet, but I didn’t think much about it. So I put on my shorts and a t-shirt and went into the kitchen. Her moaning finally quieted down or stopped altogether. I drank a large glass of water and was getting another to take into my room when Helen walked out of John’s room again closing the door behind her. She was wearing his full length dark blue robe and I assumed she was naked underneath. As she walkedI could see her smooth tone thighs where the robe met in the front. She had taken off her heels, which was probably for the best because seeing her in those would’ve probably had me growing hard again with no place to hide my arousal.

She walked into the kitchen and sat on the bar stool at the counter and crossed her legs. She said “Oh good your still here. There is something you can do for me. Get me another glass of wine.” It was more of an order, but I found it erotic to be obeying her simple command. I filled her glass from earlier and handed it to her. She asked what I was up to tonight with a slight smirk on her face. I wondered if she knew I was listening to them. While I wasn’t erect, there was a slight bulge in my shorts and she might have noticed it. I told her I was just hanging out listening to music and relaxing. Trying to sound casual and not like the pervert who just jerked off with a stocking to a mental image of her as he listened to her moan in orgasmic bliss.

She finished her glass and demanded another. I filled it as ordered and she got up to walk back to his room with the wine glass in her hand saying “Well time for round two. Maybe he will do better this time. You should get out and get laid. It’s a lot more fun than listening to music or whatever you are doing. I’ll let you know if I need anything else.” And with that she walked back into his bedroom. I went to my room, put in some ear buds and fell asleep to some music instead of listening to them screw. I don’t think I could take any more of that. My dick would be way to sore from all the stroking if I kept listening. The next morning I had to leave early so I didn’t see her leave, and never saw her again. John said she was “Kind of a bitch” and didn’t care to see her again, but I got the impression she got what she wanted from him and wasn’t overly impressed and wasn’t looking to come back.

After that night I was even more determined to get laid. My part time job and school kept me busy. So I still had trouble meeting women. One day at work I was told to report to a different department because they needed help there. I went over to the other building and got put to work right away. I was introduced to a very nice woman named Cheryl who has a very attractive face with a angelic soft quality to it, shoulder length light blonde hair, glasses, what I would guess are C cup breasts. She was in a skirt wearing tan nylons. She has shapely calves and the way her skirt hugged her thighs and butt, her sexy figure was quite obvious. Her high heels were only about inch and half tall. More for practicality of work than for style, but I kept staring at her legs. She was 26 years old about 5 ft. 4 in. tall and maybe 120 lbs. Not a model by any means, but still very pretty in an elegant and obvious manner. I knew she was out of my league, but my weakness for skirts and nylons were getting the better of me. She was my part time supervisor while helping out in the new department. We worked together a lot and she caught me looking at her several times. I was 23, almost 24, at the time. I am athletic and have a descent build, but I’m nothing special. 6 ft. tall and about 165 lbs. No big muscles or 6 pack abs or broad shoulders, but I exercised when I could just to stay in shape. I have short brown hair and would’ve said my looks were average.

Cheryl always wore skirts to work. Nothing flashy just simple plain colors that were either just above or just below the knee. Always looking feminine and professional at the same time. I couldn’t help but stare at her shapely calves and she always wore nylons. As I worked I’d be wondering if they were held up by a garter belt or if they were pantyhose or just stay up thigh high nylons. I would try and make small talk with her whenever I could and even tried flirting a little bit, but I’m socially awkward and am not good at talking to people. Especially women. Especially women I’m attracted too. She didn’t seem to mind my awkwardness, and would do more than her share to carry a conversation. Often giggling when I tried to be funny or amusing. I had spent three weeks working with her and knew I was about to go back to my regular job in the main office building. I decided it was now or never to ask her out.

I didn’t have much of a chance with this beautiful woman, but I was thinking with my penis and not my brain. As my supervisor it may have been wrong for her to go on a date with me from a professional point of view, but that was about to end. When we were finally alone in the break room I pointed out how it was my last day tomorrow and wondered if she would like to get a drink or dinner Friday or Saturday night. She said, “You’re cute and I’ve liked working with you so sure why not”. It wasn’t exactly and enthusiastic response, but it was still a yes. A yes from a beautiful woman. For three weeks I’d been staring at her legs then going home and jerking off to the idea of running my hands up and down them, of kissing them, and of licking them. Now I was going to get a chance if I just played my cards right.

After work Friday I went home showered, changed clothes and met her at the restaurant she had chosen. I was crushed to see she wasn’t wearing a skirt or heels. She still looked stunning in tight jeans and loose fitting top. The restaurant was fairly casual so it was appropriate attire, but I still longed to run my hand up her legs under her skirt and hopefully bury my head between her thighs. I guess I had very high expectations for a first date between us, and for no other reason than I was horny. Dinner went well and I had a good time, and I hoped she did as well.

As the night went on I had forgotten all about touching and kissing her legs and of the chance of getting laid. I just enjoyed being with her. However, I felt something was missing and it wasn’t just her skirt. She must have a good time too because she said we should see a movie Saturday afternoon, and asked me to pick her up. I eagerly said yes and walked her to her car. She gave me a quick kiss goodnight and said she’d see me tomorrow.

When I got home I was still overly optimistic about my chances with her, and even though I had a good time talking with her I was still trying to figure out what seemed to be missing. I realized she wasn’t acting as my supervisor anymore. She wasn’t telling me what to do, she wasn’t in charge and I liked that aspect of our interaction together in some ways. Looking at porn online had led me to a lot of different fetishes and interests. My love of women’s legs sometimes led to images of dominant women having their legs worshipped. That type of thing never occurred to me as something I’d enjoy, but the more I saw the more I looked for it. I was starting to think I had a submissive side, but wasn’t sure if it was truly that or just my fetish for legs and nylons, and my desire to have sex for the first time. Mostly I had enjoyed just spending time with Cheryl. Not being bossed around was just different. It was not a problem for me. She was easy going and put me at ease on our date.

The next day I picked her up at her apartment and I suggested she pick the movie for us to see. She was wearing jeans and a casual shirt again, but still her attractiveness was obvious. No luck on skirt and heels again. On the drive there she said she’d like to cook me dinner after if I was interested. I immediately said yes probably sounding overly eager.

The movie was fine, but I kept thinking about going back to her place. When we got there she led me in and we sat and talked for a few minutes. She got up to make some pasta and salad and I followed her into the kitchen offering to help. I enjoyed our time together and talking with her was easy and natural, which is not normal for me. I was really starting to like her and had actually stopped thinking about what might happen sexually. Dinner was good and we talked for hours after eating. The less I thought about sex the better the date seem to go.

Eventually while sitting on her couch she leaned in and kissed me. I took the hint and leaned over and kissed longer this time. We started making out and gently touching each other. She pushed her tongue into my mouth and played with my tongue. I did the same to her and sucked on her upper lip. I ran my hand up the outside of her jean covered thigh several times. I carefully felt her perfectly pert left breast. Eventually she reached down and rubbed my cock through my pants. Up until now I’ve had experience with making out a few times with girls in college and high school, but this was now new territory. I got very hard very quickly. This continued on for about 30 minutes when she finally pulled back from me. I had one hand between her legs rubbing her through her jeans and I thought maybe I had gotten a little too rough or had gone too far. I thought it was over and she was going to ask me to leave when she said “It’s getting late, why don’t we go into the bedroom.” I stood up and she grabbed my hand and I followed her to her room.

She said she would be right back and stepped into the attached bathroom. I stood there not knowing what to do. In a minute she returned. She stepped towards me wearing only a black bra and matching lacy panties. She pointed out that I was very over dressed. I should’ve already gotten down to at least my underwear but was too inexperienced to know that. She lit about a dozen candles and then shut off the lights. I slipped off my clothes standing before her in only a pair of checkered boxer shorts my erection clearly showing under them.

She reach forward and grabbed me by the cock and said “I’m glad you approve of my attire”. I nodded and said how sexy she looked. We laid down on the bed. My hands roamed over her body. Taking my time not to miss an inch of her. As we kissed and touched I had a sudden realization and got very nervous. Not just because this was a first for me, but because I had really fallen for her and didn’t want to mess this up between us. I figured if she likes me before sex hopefully she still will after. I kissed her lips and neck as I explored her. Her panties were cut high on the hips and showed off her legs. I kept drifting my hand back to her legs while she reached into my shorts and took hold of my eager dick. “Someone is ready to go isn’t he” she said. I paused trying to think of what to say when she realized what was going on.

“Oh my gosh, are you a virgin?” she asked compassionately. I could only nod in embarrassment. “Is that ok?” I asked. She just smiled and seemed to like the idea of taking my virginity. I went back to kissing her and she ran her hand up and down my rock hard shaft. I thought I would have good stamina when I finally got to have sex because of how much I masterbated, but the feel of someone else touching me was quickly bringing me to the point of no return. She was incredible at how she stroked me, and I pulled my hips away from her hand and started kissing down her chest. I hoped she didn’t realize I was trying not to cum already and that I just wanted to explore her sexy body more, which was definitely true. She reached up and slid off her bra for me. I took her right nipple into my mouth and licked and sucked it. Her full breasts felt amazing in my hand and mouth. This was better than I had ever imagined. My right hand slid between her legs and played with her pussy as best I could through her panties. I didn’t know if I was doing it well, but I could feel her wetness through them. I could’ve slipped my hand inside of them easily just as she had done to me, but I didn’t realize it at the moment.

I swirled my tongue around her nipple and sucked on it. Then I’d start kissing the rest of her breast trying not to miss a spot. I’d keep alternating between left and right. I was enjoying every second of it and was not calming down much. I desperately hoped she was enjoying it as well. I decided to be bold and take a chance so I slid down further and began kissing her stomach. As much as I enjoyed the feel of her hard nipples in my mouth and sucking on her firm breasts I wanted to feel her thighs wrapped around my head. It was selfish to be thinking about what I wanted, but at the moment I was just so wrapped up in the experience. She laid back and let me move lower. I planted small kisses down her tummy and sides as I tried not to seem over anxious to plunge my tongue inside of her. She gently put her hands on my shoulders and encouraged me to go lower. That was all I needed and I moved down and softly kissed on the front of her panties. My hands roamed up and down her legs as I kissed her crotch. Occasionally moving to the edges of her panties or even kissing her hips.

I was lost in lust and desire. I started kissing her left thigh while I rubbed her pussy through her panties. Then I moved back up and kissed across the small strip of fabric right over her pussy lips. She moaned softly in approval. I started kissing down her right thigh all the way to her knee. Then I licked up her leg to her now dripping cunt. I carefully grabbed her panties and began sliding them down her legs. I kissed each leg as I went until I slid them off over her feet. I kissed he tops of her feet and then the bottoms then kissed and licked my way back up until I was inches from Cheryl’s bare pussy. It was shaved smooth and looked perfect to my virgin eyes. I placed a soft kiss right on the lips and then as gently as I could I licked up and down each side. I was new at this and nervous and desperately wanted to make her feel good. I had read and seen enough online about going down on a woman to know what I was supposed to do in general, but this was finally the real thing.

Each woman is different and this wasn’t a porn actress getting licked for a video camera. After teasing her as much as I thought I should I pushed my tongue against her sex and made a long hard lick from the bottom all the way up to the top pressing hard and getting my tongue as deep as I could inside her wetness. She moaned and put her hands on the back of my head holding me in place. I licked and kissed her pussy. It took some time but I figured out where her clit is and licked it often before going lower and slipping my tongue into her wet folds. Then I’d move back up and flick her clit with my tongue before sucking it between my lips. She started to squeeze my face between her sexy smooth firm thighs. I was in heaven. I kept licking and sucking and finally she cried out “Don’t stop, don’t ever stop, oh FUCK I’M CUMMING!” I licked her clit for all I was worth. I didn’t care how hard she was squeezing my head between those sexy thighs or how hard she pushed my face against her crotch. I was loving every second of this experience. After a minute she unlocked her thighs from my head and pushed my head back and away from her. I was worried I did something wrong, but she just needed a minute to calm down. She was hyper sensitive at the moment and as much as I wanted to keep going down on her she need some time.