My Virginity Revisited

I was walking down the street one day in the middle of the city, when I heard someone call my name. I turned around and saw an old friend, Josephine or just Jo, who I had not talked or seen in 35 years. We both said “Hi.” We had the usual conversation that we must catch up on things after all this time. Jo said, “How about dinner tonight after work.” I said, “OK”. We meet a little after 5PM at a quiet romantic restaurant. Jo was a petite and slim older woman. Jo was the person, who I had lost my virginity to and had first time sex with. She was about 10 years older than me, but still was very beautiful and lovely. I was 55, so I guess she could be 65, but she looked very hot after all these years. Our evening went just fine. We had great conversation and caught up on our lives with each other. After dinner, still early Jo suggested to stop at her place for a nightcap. I said “Ok,” and we went off to her place. I met her in the parking lot and we went into the building. I asked her, Do you remember how I asked you if I could kiss in the car and the lust in the elevator.” Jo said, “Yes, It was great. Are you going to ask me if you can kiss now. We’ll the answer is yes and more if you want.” In the elevator, we kissed all the way up to her floor. We got out of the elevator and she looked at me like we were teenagers. As she unlocked the door, I kissed her very passionately and picked her up and carried her into the apartment. She said. “Thank you.” I put her down and Jo locked the door. I said, “I am sorry. I do not know what came over me.” Jo said, “Don’t be sorry. I enjoyed the contact. It was fun.” We went into the kitchen and Jo poured a glass of wine for both of us in one big wine glass to share. When done, I twirled her into my arms and kissed her again. We walked into the living and she asked if I might enjoy some TV. I said, “I would prefer you naked and to have hot, steamy, kinky sex with you.” I apologized to Jo, but she said, “Do not apologize. My body is much older than the first time we had sex together. But, I am up for any type of sex you want.” We finshed our wine together and had another glass and took the wine into the bedroom hand in hand. Jo said “What type of sex or activities you do have in mind tonight.” I said “I wanted to do everything with you, but I have one question that I have been wondering for years. Was that the first time you had sex with anyone when we did it.” Jo looked at me and said, “Yes. I guess I was much older that most girls when they have sex for the first time. Do you want to know how old I was when we both did it. I was 32. So now do you still want to have sex with an old woman, who is 67.” I said, “Jo, I want to have straight sex, oral, anal and kinky sex with you tonight and more. I am going to get you totally naked and complete your 67 year old body like you never have never been before.” Jo looked at me and said “Strip my clothes off me and make me you slave of love to satisfy you totally. Let’s do it anyway you want. I want you inside me ASAP.

Jo was in her beige business suit and dark nylons with brown high heel shoes. She still looked very stunning. I thought to myself my virginity is reincarnated. How lucky I am. I walked over to Jo, knelt down, took off her heels, and put my hand under her skirt, ran my hands up her legs and ripped her nylons and panties off her ass and legs and lowered them to her ankles and off her feet. I then kissed her pussy so passionately that she groaned with pleasure. I took off her skirt, suit coat and blouse. Standing there with just her bra on, I unhooked it and threw it to the floor. I took off necklace, rings, watch, toe rings and other jewelry until she was totally naked. While standing there naked, I quickly undressed and was totally naked with her. I picked her up and carried her over to the bed. I told Jo that I am going to fuck her like you has never been fucked before. Jo looked at me and said, “Fuck me hard and fuck me fast and fuck me deep and fuck me long. I do not usually swear, but I want sex with you so much tonight that it hurts.” With that comment, I was on top of Jo and my penis sent in deep, fast, and hard as we were still kissing. It was moving in and out with such force that Jo just kept screaming for more, while her body was more in mid air than it was on the bed. When done, we laid on the bed facing each other kissing as my penis was hardening. I told Jo to touch my penis, but she seemed timid. I got off the bed and went into her closet and found a nice pair of high heel with a purple suede finish. Jo said that she was sorry that she could not touch my penis. I said to her not to apologize, but just do what I say. She said she will do better, but not to be mad or upset. I told her that I am not upset, but I want to have to fulfill her life and have more sex with her. Jo said that she would be more accomodating. I put these suede pumps on her feet and kissed her feet and thighs. She looked so hot. I turned her around on the bed and told her to hold on to the bedpost. She seemed very unsure of herself and more slowly to go to this positon. I told Jo this might hurt, but I want to experience everything with her tonight. With my cum still dripping from my penis, I moved my penis up and down the crack in Jo’s ass very slowly and Jo just sighed and enjoyed the feeling; finally, my stick found her asshole and my penis thrushed into her ass in and out. She said it hurt initially but then began to really enjoy it and started to say “yes. Give me more. I want more.” Now, she was relaxing more and more and getting into it. When done, we sent into the bathroom. She did not want to touch my penis, but she sure did enjoy the anal sex we just had. I told her to clean off my penis. Reluctantly, she got a wash cloth and started to clean off my penis. Finally done, I kissed and Jo seemed happy. Standing naked in her purple suede heels, I said “are you ready for something different?” Confidently, she said yes. While we both were standing there, I kissed her and quickly ran my penis into her pussy time and time again. I told Jo to get shaving cream and a blade. I creamed her pussy up and shaved her clean and she did not say a word. Then, she shaved me. When done, we went back to the bedroom and I told her it is now time. She said she had never given a guy a blow job and was ashamed and afraid that she could even do it right. I told Jo that it does not matter if it is right, but just do it and I will lead her through it. She said okay. I told Jo to kneel down, hold my stick, and kiss it. This she did. Then, I told her to put my dick into mouth and slide her mouth all the up and all the back on my stick and when I cum to swallow it all. She said she would try her best. As her mouth moved up and down on my penis, she began to like it. Before we knew it, I was holding her head firmly and pumping load after load into her mouth and Jo was taking it all. When done, she kissed me and thanked me. I said it was my pleasure and I hope it was her pleasure as well. Jo nodded yes. I told Jo to curl her tongue and try to get it inside the hole of my penis. Jo had no problem curling her tongue and I cummed right away into her. Jo said that she will try to get better at this for me. I told her she could practice all tonight and tomorrow night until she gets it right. Jo agreed. I asked Jo if she had a short pair of black nylons that went up to her thighs and she got them for me. I put Jo on the edge of the bed, took her sweude heels, put on the nylons, then put heels on and extended her legs up in the air. By messaging her smooth and silky legs with my hands and then placed her legs over my shoulders, so that both of her holes were exposed for direct penetration. As I touched, kissed, carressed her perfect legs, I realize that I wanted to fuck her even more. I ran my fingers up the back of her legs, thighs, and ass, and her eyes closed enjoying the pleasure. I told Jo that I just wanted to screw her even more now. She said “great and do it hard.” I put my penis in her pussy and then put it in her ass and moved back and forth and in and out. It was so intense that her body quivered in sheer ecstasy and her high heels fell off her feet. I just kept banging my penis in both of her holes so easily and effortlessly as Jo just screamed for joy. When done, I put a pair of red flats on her feet, placed her back on the edge of the bed, raised her legs over my shoulders again, and to her surprise kept inserting my penis into both of her holes until again the intense joy allowed her flats to fall off her feet. Jo looked and said “you are very good.” I told Jo that you are saying that because you have never been fucked or had intense sex with anyone in your life. Jo said that I was right, but I was still very good. Now that you have been fucked in every hole and in every way, she can say that she finally has enjoyed the way sex should be enjoyed and can now die, but I am not done with you yet.

Next, I took off her nylons, found another pair of old black high heels and went to the bathroom. I drew a bath for us and I went in the tub first; then, I helped in the tub with her heels on. I laid now first, she laid on top of me. I washed her back and ass as we kissed. Our kissing intensive and my penis hardened and went into her pussy. Again,her heels came off. Then, Jo got on the bottom. I kissed her neck, which really turned her on, and rammed my penis into her pussy again. We got out of the tub and I dried Jo off with the towel. I put her heels pack on and we went into the shower together. I went in first and help Jo into the shower with her heels. I told Jo to knell down and kiss my penis, and She did readily. She looked at me and said, “I know what to do.” Jo put her hands around my waist and sucked on my stick like never before and made me hard quickly, so I could cum into her. She swallowed my white cum time and time again–always wanting all of it. After this, we got out of the shower and dried each other off and went into the bedroom. I put the purple suede high heels on her feet and we went to bed. The next morning, we woke up together at 7AM. Before we actually got up, I kissed Jo and gave her some good morning sex in her pussy to get her day going. Before we left for work, I asked Jo to meet me at the door the next evening totally naked with only her suede purple heels. She said that she would be glad to do that. I also told her that I have something else planned for us tonight and that she must agree now that we do it. Jo said that after last night, she would do anything I want of her. I told her that I would hold her to that. Jo said, “OK.”

End of Part 1

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  1. Anonymous says:

    Well, it’s a change from your other stories in a sense. Your punctuation is a bit better along with your grammar. Still a bit boring though. I personally am not turned on by two old people going at it. Definatly better then your other stories, but again, unexciting.

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