tagFirst TimeFirst Time Lover

First Time Lover


Everyone remembers their first sexual encounter. I am no exception. I was 18 years old, and the first man I ever had sex with was 58 years old. Now you might think this is disgusting, and you may want to stop reading this right here. Truthfully, he could not have been a better lover, and in the many times we had sex, I learned a great deal about mutual respect, as well as the basics in pleasuring a man, and a woman.

This man was my boss. He ran a simple store which sold various items such as magazines, candy, coffee, and other items one might grab before boarding a train. The job was easy, and I worked after school, and every Saturday. I usually ran the place in his absence, but we many times when our hours over lapped.

I discovered the joys of self pleasure around the age of 15, after discussing the advantages with several girlfriends from school. I enjoyed masturbating several times a week, and many of my fantasies I derived came from the Forum section of my brothers Penthouse Magazine. A good reading tip from a friend. At times I would think about my boss, and wondered what it would be like to have sex with him. He even would surface in my fantasies from time to time. He was a great guy to work for, and I at times wondered if he thought about me in the same way. He was always quick to share a dirty joke, and could at times show me his favorite photo of the week in one of the many porn magazines we got. He was up front and honest, but was always concerned that I keep what he shared with me to myself. I always assured him I would.

One Saturday while working together on the inventory in the stockroom, after the place had closed, he showed me a picture of this incredibly gorgeous blonde with very full breasts. He told me he thought that’s what my breasts looked like. I chuckled and told him mine were not that full, but he insisted they were. I knew this was my opportunity to do some serious investigating into a new world, so I offered to show them to him. He jumped at the offer, but again insisted it remained between us. I assured him it would. Taking my top off, and slowly removing my bra, I could feel the heat rise in my face.

I suddenly found myself in a position of not being able to go back, yet at the same time, wanting to move forward. Typical for someone my age. As nervous as I was, I felt completely safe with him, and I also thought about how I wanted this happen for some time. His eyes became full and he immediately told me he was wrong, and that my breasts were not as full, but never the less they were in his words, ‘gorgeous and full’ breasts. I could feel my nipples tighten, and he saw the reaction and remarked about my nipples being so inviting to the touch. Moving towards him, and taking a breast in each hand, I offered them to him. I wanted him to touch me, and instructed him to do so. He took both breasts in each of his hands, and soon moved his mouth over one of my nipples.

I could feel excitement stir in me, and just like when I read my brothers magazine, I suddenly felt the urge to pleasure myself. Small gasps left me, and he was soon more aggressive with licking and sucking each nipple. He began telling me over and over how much he loved my breasts, and wondered if I liked him sucking my nipples. I told him it felt good, and wanted him to do more to me. I told him, without thinking twice, that I wanted him to make love to me. He pulled me close and I felt his tongue soon probing my mouth. One of the things I remember about him was the size of his tongue. It was so broad, and long. I would often associate it with that of a large animal. My tongue responded to his, and I found myself pushing mine deeper and deeper into his mouth.

I had a boyfriend who loved the way I kissed, so I knew what I was doing at this point. He and I had not dated long, so we had not done much past heavy petting. The furthest he got with me was stroking my clit to orgasm.

He pulled me closer, and I could feel his hard cock pushing into my side. A hard cock was nothing new to me, and I knew how to stroke my boyfriend to orgasm. He had, on several occasions, try to get me to suck him off, but I never had the desire. I suddenly felt the desire now. I reached down, and through his pants, I starting rubbing his cock. He began to moan, and I continued to kiss him. He was rubbing my breasts with one, hand while the other massaged my lower back. At this point, he was not letting go, nor was I. He encouraged me to remove his cock from his pants, and wanted to know if I had ever had a cock in my hand. I told him I had, but that was as far as I got. He whispered in my ear he would teach me the right way to pleasure him.

Letting go of my breast, he instructed me to kneel in front of him. He lowered his pants removing his cock from his boxers, and then sat on a box in front of me. Instructing me again, he told me to take it in my hand, and to slowly lick the head. The head was so soft, and I took it in my mouth easily, slowly sucking on it. My tongue, under his guidance, probed his pee slit, and I soon could see a small amount of cum ooze out. He encouraged me to taste it, and at first, it seemed bitter, and salty. Listening to every word, I licked the shaft, and took his balls in my hands, and massaged them. I wanted to do each step as he instructed, but I soon found I wanted to be more aggressive. I loved the feel of it as it slid in and out of my mouth. I found it a game to see how much I could take in.

His moans moved me. I didn’t feel as clumsy as I thought I would. I loved the feel of his balls as I massaged them. I could feel them tighten in my hand. I felt as if I had some sort of power over him. It wasn’t long before he told me he was going to cum. I wasn’t too sure if I was ready to let him explode in my mouth so I backed off, and he shot his white sticky load in my hands, and up my arms. I told him I was sorry, and he immediately told me he didn’t mind. He did encourage me to taste it, and I licked my hands, slowly. He told me watching me do that was even a turn on. He pulled me close to him, and starting kissing me again. His tongue filled my mouth. Reaching between my legs, I could feel him stroke my panties. His touch was so light. I felt as if I would explode just from his touch.

One of the things I liked about self pleasuring myself was the ability to control how and when I came. I wasn’t sure I could now. I could feel him trace the edges of my panties, and asked if he wanted them off, and he told me ‘not yet.’ He seemed to enjoy teasing me, and I was not used to someone going this slow to get to me. My boyfriend could get to my clit in record time. I began to think this process might be better. I could feel my breathing increase, and I could feel small moans leave me. He lifted the edge of my panties, and pushed his finger into my wetness. Moving his fingers and hand slowly over me, I wanted to feel him push into me. He removed his finger and brought it to his nose and smelled it. He smiled and told me he loved the smell of wet and warm pussy.

Then he placed his finger in his mouth, and sucked it. This was some what of a turn on. I had often tasted myself, but this proved more of a turn on for me. He returned his finger, but this time went deeper. I felt myself lean back and spread my legs more for him. The invitation was accepted, and he then removed my panties. He then got off the box and knelt in front of me, and slowly pushed me back. He began to lick my clit in small circles, and continued to push his finger in me. I wanted him to fuck me hard, but I could not make the words form in my throat. His tongue lapped at me, and he moved it up and down my slit in long strokes. The width of his tongue covered so much of me.

He pushed his tongue in me, and I could feel it trace the walls of my pussy as he removed it. I felt like I couldn’t get any wetter. I made every attempt to keep from cumming, but I could no longer hold on. He knew I was about there, and he increased the pace of his licking, and probing. My legs seemed to clamp around his head as I exploded. His licking never stopped, and I could feel myself cum in waves. I began to move my hips in a bucking motion into him. Finally a loud scream made him stop. He removed his tongue, but I could still feel an intense throbbing in my pussy and clit. The sensation was better than I had even felt before. I really felt the need to feel him in me, and when I asked him to fuck me, he quickly told me he would next time.

He went on to say that this was enough for me today. I felt totally relaxed, and didn’t know if I had the strength to even pull my panties back on. I eventually did, and headed home. I masturbated that night and relived the afternoon again, and knew I had to have more with this man. I had the need to fuck him. And I hoped he would eventually.

We would have sex again, and again. There was more for me to learn, and he wanted to be the one to teach me. His age never bothered me. I actually felt some sense of being protected. I continued my relationship with my boyfriend, but never once let on I knew more about sex than I did. For some strange reason, I did not want to share any more than I had to with him. My boss proved to be the best lover I would ever have, and I learned everything I know today from him.

To Be Continued...

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