My first time was with my girl friend who hinted all the time but when it came down to getting it she was not so willing. How it went down. We had been heavy petting and I had been in her top a few times. She once wore a tube top with no bra knowing I would not resist her unsupported large heavy hooters. Well we could never find privacy at her house or mine thanks to our parents so on one drive I decided to take a short cut through the country which we had taken many times before. The gravel road was seldom traveled and I knew of a place to back up and make the big Oldsmobile disappear mostly from that road. So when I did she said ” what are you doing ?”with that scolding but curious tone. That afternoon that I think took no more than an hour and a half but is firmly etched in my mind. What is it you want ? She said chuckling as she put an arm around me chuckled and un buttoned the top button of her already low cut dress. It was the late 70’s and she was wearing a white button down short sleeve thin blouse and a chocolate corduroy dress to her thighs. Sort of like a bib cover all top that was connected to a dress that buttoned down the front. Knowing her lacy bra fastened in the front , I reached over and unbuttoned another button of her blouse and reached in her top and began to make out. Soon more buttons were open and her bra was open and my hands roamed where they had been many times as we french kissed. In ten minutes I began unbuttoning more buttons and she resisted some in word and very little in action. Cheryl had often worn a girdle . She never needed a girdle having a very nice figure. She wore a girdle and full panties mostly to keep me at bay. Well she had made her clothing in home economics class . The class had just finished and shown off what they had made and modeled them in a show at school . Well you have to wear pretty lacy undies to flash your goods as you walk your best walk in a show don’t you. It was only girls at the show so no modesty was needed. There was no way I could of gotten by a girdle and full panties with out some kind wrestling match. To my luck they were left some where in school because she was wearing them when she went to school that morning. It was then as I had but two buttons left to totally open her dress that she realized she was wearing a lacy white small briefs. She put both hands quickly to her last two buttons and blushed . She had always been ultra shy and getting her to expose her breast took 6 months . A panic attack came over her and I saw it . I was afraid I would loose her for a week as she would hide for a while in her home claiming to be sick. I held her and said it’s ok , it’s ok . Just then the sun came out all bright and warm and she then wrapped her arms around my neck and came back to her spunky self. This only happened to me a couple times in the 30 years I knew her , but for real she shut down many times for other people when I was gone. It’s Ok she said to me . See I’m perfectly just fine she said and she unbuttoned the two remaining buttons on her dress but held both sides together on her lap with both hands. I made this dress she told me knowing I already knew. It is very pretty I said and put my hands on hers and placed them off her lap and proceeded to open her dress which was now open from top to bottom . Her knees were tight together and I saw her lace bikini brief for the first time ever. These are so nice I said. They aren’t very protective she said. Against boyfriends Cheryl added. Let’s keep this dress in good shape I said. What if some one drives down this road ? No one drives down this road and no one will pull back here to look for us. They are going to miss us . We won’t be here forever now chill out. Let me look at these lace panties. Now I was 15 and Cheryl was 17 and I never told her how young I was or she would of flipped out . I had been lucky enough to get my hand in a few girls pants . I had even gotten my finger in two other girls vaginas . But they had jeans on and the one finger was their limit. I had never seen any girl or woman’s business end and I was getting hopeful . Soon I had her dress blouse and bra laying on the back seat . I was fully dressed and kissing my girl. She was scared she told me latter . I was just curious. I lay her on the front seat and dry humped her and she at last uncrossed her legs and I was grinding on her pussy still fully clothed. I my lips on hers and two handfuls of breast and pelvic action. I sat up and she said don’t look as I was between her legs and she couldn’t cross them. Now I had rubbed her crotch before but she was wearing shorts or jeans or that girdle. Now the only thing separating my hands from her pussy was a thin lacy panty with a cotton crotch of course. I reached and she snatched my hand . You can’t we gotta go. She tried to look as serious as she could. I mean it , you gotta stop. I leaned over kissing her and fighting her hands and rubbing her crotch as she kept trying to grab my hands and she pulled her waist band down and placed my hand in her crotch and her hand on mine . She moved my hand in a circular motion and she got very wet. I backed up to get her lace brief off and she kept pulling it up as she sat up she reached over the seat for her clothes as I took mine off. As she leaned over the seat and placed her bra on I pulled her briefs to her ankles and then over one foot. No she said in a whine. Get dressed. I got her on her back being all naked and I pushed her down kissing her and I was between her legs and her brief was on one leg. Her bra was on but I could care less about those 38 C cups for the moment. I reached down and was rubbing her wet folds and she said be careful . And I said I’m putting a finger in . Now I had never fingered her . She on the other hand had been fingered by previous boyfriends , her curious friend Becky who attempted to take her virginity and her doctor who recommended cutting her rather heavy hymen. Cheryl hated pain ,didn’t like shots and cutting was out of the question. Be real careful I’m a virgin she said. I know she has been using tampons for years so I figured it would be no problem. She guided a finger of mine in her. I’m using two fingers I said and tightly two just fit. She wasn’t happy as I finger fucked her with two .Now three fingers I said and she stopped me as I could only get my fingertips in. My boner was killing me and inches away was a wet pussy. Hay we can’t do this . I will get pregnant. Then suck it I said . So I got sucked and she got a mouth full and gagged. She spit it out , that was terrible. We gotta go she said . I really want it I said. I know you do , I’m all wide open here on the seat and you have me trapped . I rubbed my thing up and down her slit over and over . I never went soft even though she just sucked my first load. Don’t cum in my pussy she said not trusting me at all now. Don’t you dare cum in my pussy. I started plunging in only to get stopped by the hymen of steel. That’s it your done she said . I ignored her and pushed hard . Like her previous boyfriends and girl friend before me I was unsuccessful popping her cherry after every angle and method. Just quit she said. I mounted all the pressure my hard 15 year old penis could with all my weight . Then my penis folded in half and pain shot through me . I shriveled up in 60 seconds as I held my hurt member a second. We just kissed and I opened her bra and played with her breast. With my mostly soft penis I played in her wet opening using my hand to move it around. Then it hardened just a little and I used my finger to push it in her opening. I was in my Cheryl at last . Oh that feels good we agreed as I slipped my mostly soft semi hard tool in and out. Then it got hard and it was deep and I should of pulled out while I had a chance. In seconds it was rock hard and Cheryl was in pain asking me to hold still. It wasn’t terribly painful for me but it was like tying a shoe lace tight around your shaft. I couldn’t stroke my penis in her so I pulled slowly and made it to my mushroom head that was as far as I could pull out before it got stuck in the small hymen . Put it back in Cheryl said wet faced with tears. I pushed too far and hit the back wall of my Cheryl. I wasn’t very deep she was a virgin for sure . Stop back out and as I pulled she constricted on me as her vaginal wall muscles spazemed . I rotated my hips trying to loosen things up and her vaginal muscles relaxed all at once and I popped my penis completely out. Cheryl exhaled in a giant breath and fell back on the car seat. I saw some blood on my penis and wasn’t about to give up . I gave a lower angle aim with my penis and Cheryl said are you crazy your hurting my really bad , Stop. I pushed hard helping with both hands . Cheryl cried and cried and then at last it tore and she screamed and I pulled out and inspected the damage. We are done I announced and slid my tool in easily . Cheryl said you really hurt me as I began pumping in and out. I was going deeper with every minute and in a view minutes we were bumping pubic bones and I could no longer feel the back of her vagina with my penis. Her legs were now wide as she could get them. She started kicking her feet . She made noise but couldn’t talk . Then I said oh God and pulled out just in time and squirted a splash on her face and the car window over her head . Then the remainder on her belly. I grabbed tissue as she said yuck and wiped her up. I put my penis right back in her and kept pumping as only a 15 year old can , and this time I was all of 20 minutes in her smooth well open vagina. This time I didn’t pull out but shot off in her but I felt it wasn’t much . I just said I’m tired and let my still hard penis soak in her. I kissed her and sucked her breast and she said we gotta go this time for sure. You popped my cherry ! It’s been a hell of a day. Now pull out and get off me you stud. She told her parents I raped her. We got marred a year later. I wanted kids so I poked holes in my condoms so the end would rip and roll back on my shaft. We only had sex 10 times a year. It’s amazing she got pregnant twice
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Cheryl
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