Imagine a good-looking guy, tall, straight, intelligent, 20 years old and still a virgin. Sounds strange doesn’t it? Still it exactly describes my situation at the time. Sure, I’d had girlfriends. You know how these things go. They all wanted to kiss, and in some cases they even let me touch there breasts, but sex… nope. On the other hand my friends all seemed very experienced. They told me stories about how they made love to loads of women and I could only nod. Nobody knew that I was still a virgin and I was afraid of telling them the truth.
As I grew older it really started to frustrate me that I had no experience. It scared me that I might not be good enough to pleasure a girl the first time. I was frightened of having to say “I’m sorry, but I’m still a virgin.” I got depressed. Often I would sit at my desk staring outside imagining what it would be like to have sex. It didn’t matter. I believed nothing could change my solitude.
I was wrong. The big change came rather unexpectedly when I was home alone for a week. One day when I came home after school I ran into my neighbor Diana, a 40 year old blonde. Her eyes seemed to pierce me as she said “Roger! How are you? You look depressed lately.” I didn’t know what to say. To be honest Diana had been a part of my sexual fantasies for years and looking at her lovely face and big bust would only make my frustration worse. So I just shrugged and said “I’m fine Diana, how are you?”
“You’re lying Roger, I’ve seen you staring out of your window every day, something is wrong and you’re going to tell me what it is.”
“You know what, I know you’re home alone, why don’t you join me for a cup of tea.” I didn’t have a choice. She just grabbed my hand and made me walk with her. Soon we were seated in her living room.
I was staring at my tea. Diana had been questioning me for about 10 minutes now and it started to look like an interrogation. “Roger, why don’t you just tell me what’s on your mind? Are you having problems with alcohol Roger? Is that it? Are you on drugs Roger?” My god, what could I do… The longer we were talking the stranger her guesses got. When she asked if I had killed a person I finally I gave in. I decided to tell her all, but first I told her that she would have to promise to tell nobody about what I was going to tell her. She did. After a long silence I started talking. At first I told her how lonely I was and how much I missed having a girlfriend. Then as I got more emotional, I told her about my friends and how happy they were screwing around and all. Tears started flowing. I didn’t care. Talking about what had been bothering me for such a long time seemed like a relief. Then, with tears in my eyes I told her I was still a virgin…
Diana smiled. “But Roger… there’s nothing wrong with being a virgin, I think it’s a great thing you’ve waited that long!” Her soothing words made me relax a little and I had to smile as well. I told her how I could indeed have had sex with some easy girls but that I wanted it to be something special. Diana was pondering. As she opened her mouth to say something the door to the living room swung open and Frank -her husband- entered. My god, I had not expected that. Frank assessed the situation quickly. He saw me wiping away my tears then looked at Diana and asked her what was going on. To my surprise Diana told him everything. Frank looked at her then at me and he started to grin. “Well Diana, why don’t you help Roger solve his problem?” I couldn’t believe what I was hearing. Was Frank really serious about Diana helping me? My puzzled look must have been clear to both of them, because Frank quickly explained what he meant.
“Roger, Diana is a very experienced woman. If you want to she could help you loosing your virginity. But there’s one condition. I won’t interfere, but I will be watching all the time.” Quickly I thought about this chance. Frank was actually giving me permission to fuck his beautiful wife. I had dreamt of this sort of thing for years. In the mean time Diana had come to sit next to me and laid her hand on my leg. Softly she rubbed my inner-thigh. With a lump in my throat I answered. “I would love to. I can’t think of anything better than this….” Both Frank and Diana smiled. Diana said “Roger… this is going to be a very special day for both of us, I’ll teach you all you want to know. And first we are going to explore my body. I think it is very important for a man to know all parts of the female.”
Slowly Diana stood up and standing in front of me she untied her hair. The long blond hair fell over her shoulders. “Are you going to sit there and watch me undress Roger? Or will you help me out of my clothes?” I didn’t have to think long about that one. Immediately I stood up and I hugged her. I could feel the warmth of her body through her clothes. As I pressed her body against mine she must have felt my hard manhood against her belly. First I opened her white blouse. She was wearing a sexy red bra, the kind that leaves the upper part of the breast uncovered. With both hands I fondled her big tits. Often I had done this in my dreams, but now that it was for real I realized they were even bigger and softer than I thought. Diana just let me play for awhile. Then she took off the bra and asked me to suck her nipples. She sat down on the sofa and while I was holding her tits with both hands I sucked and licked one of her hard nipples. “Try going around them with your tongue Roger, and you can also bite them softly. But watch out. If you bite them to hard it will hurt me.”
After about 5 minutes of playing with her enormous tits I suddenly heard Frank again. I had completely forgotten about him, but he was sitting on a sofa at the other side of the room. I could see he had his pants down and apparently he was masturbating at the sight of me playing with his wife’s tits. When he saw me looking at him all he said was: “Go on Roger it’s OK.” Diana was moaning softly now. The continuous licking of her nipples was driving her crazy and she clearly longed for more. “Roger, lets go on exploring my body. Are you ready to see my cunt?” I had never expected Diana to say “cunt” and having this classy woman talk about it that way only made me hornier than I was. She stood up again and pulled down the skirt she was wearing. Now she was dressed only in a pair of panties and a red string. I was still completely dressed.
“Have you ever touched a pussy Roger? Have you ever been able to take a close look at a cunt?” I shook my head. “Then this is going to be the first time Roger.” I was still sitting on the sofa when she grabbed my hand with hers and placed it between her legs. Even though she was still wearing panties and a string I could feel the warmth of her pussy. “Try to rub me softly Roger, it will drive any woman crazy..” I did what I was told. Softly I moved my hand back and forth as if I was wiping her pussy. I could see Diana was really enjoying it because her nipples became very hard again and they pointed straight ahead. “Hmmmmm you’re good Roger, I think it’s time for you to really feel it now.” Slowly Diana bent over to lower her panty. Then she dropped the little red string holding one hand in front of her pussy. I gasped in awe. I could hardly believe that the sexy woman standing in front of me was actually going to let me touch her pussy. Behind her hand I could see she had her dark blond bush trimmed short in the form of a triangle.
Diana now sat down next to me again. She was almost laying on her back and slowly she spread her legs. “Roger , why don’t you kneel in front of the sofa between my legs, and take a good look at my pussy.” I did as I was told. Diana’s pussy was gorgeous. I had expected quite a hairy pussy, but there was only hair on top of it. Of course I had seen pussy on pictures, but it surprised me that her lips were so nice and tight, absolutely not the long stretched-out pussylips I had expected. To give me an even better view Diana spread her lips using both hands. Now I could look into it and to be honest it looked wet and very tight. “Try stroking my thighs and my pussy Roger, use both hands and massage my pussylips with your thumbs.” Slowly I started massaging Diana. When I traced her outer lips with my finger I noticed her shiver. “That’s good boy… are you ready to put a finger in me?” I looked at her cunt. It seemed to be very tight but slowly I let the middle finger of my right hand sink into Diana.
“Wow… this is really hot Diana.” She nodded and smiled. “Can you feel me milking your finger Roger? I’m contracting the muscles in my pussy now.” I concentrated on my finger again and indeed I could feel the pressure she was talking about. “Now try to add two more fingers Roger, but do it slowly, otherwise it hurts me.” I was surprised. Sure, I knew that babies come out of a pussy but putting three fingers in such a tight place seemed to me like tormenting Diana. Yet I did as she asked me. Having three fingers in her pussy I could feel the contraction-thing very good. “Can you also do that with a dick Diana?” She nodded. Then she explained to me that next to fingerfucking all women love to have their pussy eaten out. I hesitated. That would mean that I had to lick her and although I was enjoying myself I still though it to be something dirty.
“Try it Roger.” I had forgotten all about Frank again, but he was now insisting that I licked Diana’s pussy. “And especially take care of her clitoris Roger, she’ll love that.” Diana showed to me what Frank meant. “This is the most sensitive place a woman has. And when you lick her, try working your way towards that little knob.” I decided to go for it. Sticking your face in a woman’s genital area for the first time might seem dirty, but to my surprise I quite liked it. Diana’s pussy smelled like nothing I had ever smelled before, but certainly not like the fish I expected. First I licked her thighs. Then I worked my way towards that little knob. Slowly I licked her pussy up and down and on one occasion I even inserted my tongue. Diana was enjoying it. She moaned loudly now and if I hadn’t known that Frank was there already, I would have been frightened to get caught unexpectedly.
Licking Diana’s pussy was a great experience. I really got the hang of it, and remembering a scene I had once seen in a porn movie I slowly sank two fingers in her cunt while sucking on her clitoris very hard. That was too much for Diana. With a very loud moan she had her first orgasm. I had not expected that to happen so soon, and as Diana came she almost crushed my head between her legs. When she relaxed a bit my whole face was covered with her juices but Diana kissed me nonetheless. It was a very passionate kiss. Wild, hot and more intense than I had ever been kissed before. “Roger, you’re a natural! You can come and lick me every day!” I laughed at that. Then Diana showed her wicked smile again. “But now it’s time for me to explore your body Roger.”
Within minutes I was sitting on the sofa again, with Diana kneeling in front of me. She had undressed me very quickly and was slowly sucking on my hard cock. With her tongue she ran up and down my shaft, concentrating time and again on the place where my dickhead is connected to the foreskin. It felt great. Friends of mine had always told me that getting a blowjob was like being in heaven and now I knew what they were talking about. Diana looked at me. “I can see you are enjoying it Roger, I think it’s great you haven’t had an orgasm already. Can you control yourself that good?” I admitted that. After years of peeling my own banana I could almost come at will. Of course I should have known better. After mentioning that, Diana started to jerk me off while giving me head and unexpectedly she licked my anus and slid the top of her finger in it. That was too much for me. My whole body was shaking as I was going to cum right in Diana’s mouth. But instead, as the first cum shot out she let me spray it all over her face.
When I opened my eyes I saw Diana’s lovely face covered with my cum. Big white drops of my sperm were in her hair and some of it was even on her eyelashes. Immediately my soft member got hard again. Diana was surprised. She said that she really badly wanted me to fuck her now, but there were a few things I had to know first. “Roger, always remember that having sex without a condom is not safe.” I nodded. At sexeducation they had told us that hundreds of times. “But considering you have never had sex before, and considering the fact that Frank and I have never had sex with other people I’ll make an exception for you.” I grinned at the prospect of fucking Diana. “If you want to, you can shoot your cum deeply in to me, but I would prefer it if you spray it all over my pussy and my tits.” I nodded again. Who am I to say no to things like that. “Finally remember that you always have to keep in mind that you are trying to pleasure a woman. Look at her and see to it that she’s enjoying your cock.”
Now it was time for the ‘moment supreme’. Diana asked me to install myself on the rug that was in front of the fireplace. I took a cushion from the sofa and laid down on my back. My dick was pointing straight in the air. Diana came to stand right above me and sank through her knees to sit on my chest. I could feel her wet pussy as she slowly slid down my belly towards my dick. When she was almost there she lifted herself up and grabbed my hard member with her right hand to position it in front of her cunt. “Are you ready Roger? Here it comes.” Then she slowly let it slide in. This was a feeling I had never experienced before. The tightness, the warmth and the heavenly softness were overwhelming. Diana had been looking me right in the eyes as she slid it in and I could see her eyes widen as I completely filled her up. Then she started moving. I raised my hands to hold her swinging boobs and I enjoyed the heavenly ride she was giving my dick.
Frank had now moved closer to us. He was still jerking himself while I was fucking his wife. I could hardly believe it. Meanwhile Diana closed her eyes and started fucking me like crazy. “Oh yes Roger… yes… I want to feel you deep in my tight cunt. Fuck me like the whore I am.” Her dirty talk was turning me on even more and I realized for the first time now that I was not a virgin anymore. After about 5 minutes Diana said she wanted me to be on top so we turned. My dick was out of her pussy now, glistening with her saliva. Soon it would be back in again. Diana begged me to penetrate her quickly but I decided to wait a little longer. I knelt down between her legs and rubbed her clitoris with my dickhead. She moaned. “Are you enjoying it Diana?” I asked. Then at once I thrust my whole shaft deep inside her cunt. She now moaned really loud.
We had fucked for over half an hour when I knew that I was going to come soon. “I’m going to cum Diana, I’m going to cum!!!!” I sighed heavily while speaking those words and Diana opened her eyes. “Squirt your cum all over my body Roger, I want to feel your hot load on my pussylips.” I was almost there. I looked at my dick sliding in and out of her snatch and it drove me nuts. One more time I thrust my dick in and then I pulled it out and jerked off above Diana’s heavenly body. I then pointed it at her pussy and shot my wad against her lips and in her bush. I kept cumming. Seeing my own classy neighbor on her back, her husband jerking off on it, and my sperm all over her cunt was just too much. When I came back to my senses I could see Diana grin.
“Roger… you’re not a virgin anymore.” I answered immediately: “I know Diana… All thanks to you!” We decided to take a shower together and talk things over. I wanted to fuck Diana every day and later that evening Frank and Diana talked things over. Frank admitted that it had turned him on very much and that he didn’t mind doing this more often. Diana could only smile. She told me that I still had a lot to learn and that she was willing to help me out. She was the best teacher I could have wished and over the years she has taught me well. The memories of a virgin end here but maybe I’ll tell you more about my apprenticeship later on.