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Teaching Theresa

Posted by: SoloTouchArchive Author: strait8 Posted on: 19 Aug 2004 2 comments
4 likes views Category: Sex Stories Anal Tags: Public masturbation

Teaching an old girl friend about anal sex. The true story of teaching Theresa.Theresa has been a friend since grade school. We went out in Grade 10 for about a year. We did a lot of stuff that went as far as third base, but did not really have sex till three years later when she came home from McGill University in Montreal. Throughout all this off and on relationship we remained solid friends. She taught me a lot about women and how to pleasure them and I may have taught her a thing or two.Terri, had gone on to become a teacher at a local high school. She had matured into this beautiful woman. She was the picture of Italian womanhood with long dark hair and shapely, muscular curves. I am sure the boys at her school were drooling over her all the time.We used to get together from time to time to shoot the breeze, and catch up on each others lives.One day I invited her over for dinner at my place. I hadn't seen for a few months.She came wearing a pair of beautifully fitting jeans and a tight yellow top that showed her curves. Terri looked sensational.I made us an Italian dinner because i wanted to show her how well I had mastered this cuisine. I was lucky, it came out great and she loved it.During dinner she told me she had a new boy friend. I was happy and a bit jealous all at the same time. I asked how it was going, and she said good, but it seemed to lack conviction. I pressed her a bit, and she got a bit flustered. I said to her you don't have to tell me, but I am your friend anything you tell me will be ok with me.She looked at me and said: " Have you ever had anal sex with girl?" I said: "Yes I have a few times." "Robby wants me to have anal sex with him and I have never done that. I am afraid it will hurt to much. Also I'm not sure I should, being catholic and all. I am embarrassed to talk about this with any girls I know. You were the only person I thought I could ask. Robby told me that if I really love him I would let him do that. He is really well built and i think he is much too big to go in there. What should I do."I said: "First of all your boy is wrong trying to force you you with the "If you love me you will do it" bullshit, That is wrong. You do not have to hurt yourself for his love unless you want to. Anal sex will hurt especially if he is not gentle and if you are afraid and tighten up.""Let me ask you a couple questions, you don't have to answer them if you don't want to. Have you ever had any curiosity or fantasies about anal sex? Were they exciting as fantasies" She said: Yes, I have and they were a turn on." "Have you ever watched an anal act in a porno movie." She said that she and Robbie watched a couple of them, a while ago, when he was trying to convince her to try it. She said: Yes they did turn her on. I asked her if she thought the girl was in pain, and she said "No after the beginning the girl was definitely into it and possibly even orgasmed."I told her: "Not everybody is the same, but you can train yourself to take a cock in your ass. It is a matter of stretching the muscle and relaxing, but you gotta want to do it." "I would like to do it, but I am afraid""You should go to a sex shop, and buy some toys and lube and start practicing." I said to her."I could never do that, I could never go in and buy toys for anal sex, I'd die of embarrassment.""OK, I understand." I'll tell you what, if you really want to do this for your boy friend, I will buy them for you." She said ok. A couple of days later I went to my favorite sex store and bought her two different butt plugs, and a lifesize cock in a softer more flexible material than plastic. I also asked for a primo lube and they recommended a new English water based lube that did not sting like KY.I called Terri and told her to come over and get her toys. She came over that evening, I ordered in some pizza, and we cracked a couple of beers. After we ate she surveyed the collection of toys I bought for her. The first thing she said was: "I can't take these to my apartment, What if Karen (her roomate) finds them? She is always in my drawers." She'll think I'm a complete slut."At that pronouncement the little head perked up immediately and said "Tell her she can try them here, She can practice here all she wants." So the big head said just that. I didn't think she would go for it, so I added with a smile: " I will even volunteer to help train you if you want. "She looked at me and slowly said: "Yes ok, but one condition, you can't fuck me." Little head got an instant headache, but the big head said: "OK, I can live with that, as long as you get me off like we used to do in high school. She giggled and said: "Ok"So I said: "Strip down and I will run a bath for you. I want you to relax completely. I went in the bathroom, lit 4 vanilla candles and ran a warm bath for her. I took out a robe for her and met her as she was down to her bra and panties. She looked so fine, golden olive skin, big brown eyes and curves that were beautiful. I said: "You are more beautiful than ever. Boys at school must have to take bathroom breaks a lot in your class to relieve the tension." She said: "I think I have a couple that do, and I have one girl who I am sure is at least bisexual, who is always staring at my breasts."I sent her off to the tub and told her to soak for a while. After about 15 minutes I went in to see how she was doing. I asked if she wanted me to wash her back and give he a neck massage. She said sure, so I stared soaping her back and slowly massaging her neck. I did that for a while then expanded the field of massage to her soft breasts. Her golden brown nipples were hard as I lightly brushed over them. I massaged her breasts as she softly began to moan. I let my hands slide lower to her pussy. and I brushed the sides of her lips never directly touching her clit. Her hips started to lift off the the bottom of the tub. I knew she was getting horny. "Let's get you out and started on your Greek training session." She laughed at that reference and got out of the tub into the the big bath towel I held for her. My cock was just raging. It was so hard it could have been marble."Put a towel on the bed and lay down on your stomach, I am going to give you a massage." I got some massage oil and started to massage her back and legs leaving her bum till last. I warmed some oil in my hands and started to massage her golden globes. Her skin was even more beautiful oiled. She spread her legs a couple of inches. I poured some oil at the top of the crack of her ass and watched slid slowly down over her asshole. She gasped as it touched her there. I let my thumbs slide up and down her ass, not quite touching her pucker. I then slid a thumb across her asshole, her hips jumped and she moaned a deeper moan.. Working on her asshole with my thumb, while I massaged her cheeks. Her breaths were shorter as I started to apply a slight pressure. I noticed her asshole flaring slightly begging for my finger to come in. I stopped massaging her and she looked at me said: "That feels great." I replied: "I am just going to add some lube, and then I am going to put one finger inside you." She turned her head and buried it in the pillow. I poured some lube on her asshole and my finger. Slowly, I started to push into her tight hole. Terri moaned as she felt the intrusion. I told her to bear down with her anal muscles and it would go in easier. She did and my finger slipped in to the middle knuckle and then all the way to the joint. She was moaning and lifting her hips. With my other hand I started to lightly brush her pussy lips. Her legs flared open to give me access to her rose. I began to touch her pussy. She was into it now, Her ass began to fuck my finger as I slid it in and out. I didn't want to come yet so I stopped touching her pussy and pulled my finger from her ass. She moaned in frustration. I said to her: "I want to try a butt plug, the smaller plug." I lubed the plug which about 1" across at the widest point and 4" long. Pushing it slowly into her ass was so erotic. I started to describe it to her. "I can see your ass flaring around the plug, It is so sexy." I pulled out and watched her try to grip at as it came out. I then slowly pushed it in deeper to about 1", and pulled it out again. She moaned as it moved in her ass. I pushed in to its widest point, and then pulled back. I then added a bit more lube and pushed it all the way till her ass closed around the narrow neck. "OH, that feels good." she said. I spread her legs and grabbed the base of the plug with one hand and started to touch her pussy with her other. It took only a few thrusts in and out and me massaging her clit to make her scream out as an orgasm hit her. She was bucking and moving like a bronco asher cum gushed from her pussy. It was gorgeous. The smell of her sex was driving me crazy. Slowly she relaxed and said: "That was great."She turned over and I looked at her from head to toe, she was like a dark Botticelli's Venus, with her hair curly and fanned out. Her pussy was open, wet and red. After a minute I asked if she was ready for more and she said: Yes.I told her to lay on her back and pull her legs back. The plug was still in her ass. I pulled it and she moaned as the wide part came out. Her ass was gaping open. I went to the bathroom and got my shaving mirror and showed her her asshole. It was still flared open and red. I told her I wanted her to watch the larger plug going in. I put a second pillow behind her head to prop her up. I told her to watch closely. The second plug was much wider than the first. I told her to look at how it was as thick or thicker than most cocks. I oiled the plug and then told her to pull legs back as far as she could. I held the mirror where she could see it, and slowly pushed the plug in. As she watched her breath shortened and her face and neck flushed as her eyes were glued to the intruder. I told her it was the sexiest, nastiest thing I'd ever seen her do. She looked at me and said "Yes it certainly is both of those." I pulled it out and gently pushed deeper each time as she moaned. The plug was buried to its almost its widest point. I pulled it out again and told her I was going to bury it all the way. I added some lube and pushed gently and a gasp later it was buried in her ass. "How does it feel"?"Different, I have never felt so full, yet I am so horny.""Touch yourself", I told her.Her hand moved to her clit and I started to move the cock in and out of her ass. Her eyes never left the mirror as she touched her clit. Her hips were pushing up to accept the dildo on each sroke. Her hand began to move faster and I watched the classic orgasmic flush on her neck and face. Her cream poured from her pussy and down on my hand which had the plug buried deep in her ass.Slowly she came down and looked at me and said: "That was an incredible orgasm.I thought I was going to black out.""Well," I said: "The only thing your missing now is the feel of hot cum shooting in your ass as you cum. Girls tell me thats the hottest thing about anal sex. She laid their sweaty and gorgeous and then looked at me and said: "Its your turn."I slipped out of my pants. The little head had been straining for so long he thanked me when I freed him.I laid down naked on the bed, Terri knelt beside me and began to lightly stroke my cock while she looked me in the eye. She took my cock in her mouth and gently began to suck on it. I noticed her other hand slid between her legs and massaged her clit. Terri was a great tease, she always knew how to bring you to a point, and then ease off. I noticed her breath getting shorter as rubbed her pussy.I started to get close, she stopped suddenly and said: "I want you to take my cherry. I want to feel your cock there."The little head was getting a swelled head. He was stand and cheering. I said to her: "Honestly, I'd be honored, Are you sure thats what you want." she said: "Yes" and smiled.I asked her to turn around and put her head on the pillow and her butt in the air. I knelt behind her and looked at my prize. I lowered my head and began to tongue her ass, as I played with her pussy. She moaned: "Oh thats incredible." I really didn't have it in me to do this for long, so I put some lube on two fingers and gently pushed them into her ass as she moaned. I moved them from side to side to stretch her. I then took them out and lubed my dick. I lined my cock up with the target and slowly pushed my cock into her ass. After most of the helmet was in, I stopped and grabbed the vibrator, turned it on and gave it to her. I figured once I was in I wouldn't last long and I wanted her to come. I slid back in and continued to push till she moaned in pain. I stopped, and enjoyed the silky feel of her tunnel. I asked her to bear down and try and push me out when she was comfortable. after 30 seconds she stated to push and I pushed in deeper into her rectum. She put the vibrator to her clit and i began to move in and out in her ass. Within three stokes, I was buried to the balls in her ass. She was going: Oh God, Oh God. I could feel the vibrator against her clit. An orgasm started to build up, and I could feel myself starting to move more quickly and she met my pace. On the down stroke, I pushed deep and began to shoot my load. Terri screamed as it she felt it scorch her rectum. Her climax hit her hard and she wailed as it ripped through her. I felt her ass clenching around my cock sucking the cum from it.Slowly we came down and lay exhausted on the bed. I pulled her to me and she put her head on my chest. "So how was that," I asked. "It was great especially when you came, but my bum is sore, and I may not walk right for a few days.""Well with practice it will be easier and less painful.""Yea that easy for you to say, your the guy.""I think its nice to know that every time you sit down for the next couple of days you will think of me."Terri stayed the night. I think she was a bit embarrassed in the morning. She didn't have too much to say, but kissed me on the cheek, and said thanks for every thing.A couple of months later we were together with some friends. I asked how things were going, She said Robby was history. Then she leaned over and whispered in my ear: "I know why they call it Greek sex, its because Greeks do it better than anyone else."The little head and the big head both swelled with nationalistic pride link