Deflowering Jeanette

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Deflowering Jeanette
As stated at the end of this story: “Stud” of the shelter, I promised a woman named Lynette that I would meet her granddaughter, Jeanette, and possibly have sex with her. I met Lynette at a battered women’s shelter that my, mom, sister and I had to stay at because of a domestic situation at home. I also had the pleasure of fucking Lynette several times while staying at the shelter. I was still a minor teenager as were the girl I deflowered and other girl I fucked.

The summer was coming to an end and school began. The first two weeks to a month were kind of crazy and very busy. I barely had time to look for and try and meet Jeanette, let alone have a conversation with her. We did have a couple of classes together so it was going to be easy to contact her in person.

To describe Jeanette is to say she was a spitting image of her grandmother Lynette but was a lot younger and had a larger ass. She was a teenage BBW.

It was during the second month of school that I decided to make my move. I had not had sex for a while and would have fucked anything with a pussy and tits. After one of our classes I started talking to her in the hallway. We talked about the class and an assignment where we had to partner with someone. I asked if she wanted to work with me. She said sure since no one else had asked her. This was Friday so we set a time for me to come to her apartment over the weekend. She gave me her number and I told her I would call. I called her on Saturday and another person answered the phone. I asked for Jeanette and the voice said who is calling. I told her my name and all of a sudden the voice said, “oh hi baby!” I asked who it was as I did not recognize the voice. She said it is Lynette. Apparently Jeanette lived with her grandmother but did not tell her about the school project. We talked for a little bit and I told her about the assignment and she told me to come over. On the way over I was really hoping Jeanette was not going to be there because I really wanted to fuck Lynette. I got there and Jeanette was there and we worked on and finished the project.

Before I left Lynette came and talked to me while Jeanette was in the bathroom. I started to make a sexual move on her and she responded in kind. But before we could go any further we heard Jeanette coming out of the bathroom. I had to go home and Jeanette walked me downstairs. On the way down she said she saw her grandmother and I making out and asked about it. I told her a made up story that her grandmother told me she was lonely and I wanted to make her feel better. Jeanette then said she would like me to do the same thing with her too. The hallway had a blind spot so we went into it and I started kissing her and put my hands up her shirt. I lifted her shirt up and started kissing the tops of her tits. I undid her bra and her huge tits flopped out and I started sucking the nipples. I then tried to get my hand down her pants. She stopped me and told me she is a virgin. At this point I did not know that. She said she did not want me to fuck her there in the hallway. At this point I had my cock out and she had her hand on it stroking it. She got down on her knees and started to tit fuck me but did not suck my cock into her mouth. It did not take me long to cum between her tits. I left and went home.

On the way home I was wondering how she knew about stroking and tit fucking a cock and how she was such a good kisser. I decided to ask Lynette. When I got home I told my mom I have to call and let Lynette know I made it OK. I called and Lynette answered the phone. I told her what Jeanette saw us doing when she came out of the bathroom. She said she will talk to Jeanette about it. I told her to tell Jeanette about our relationship at the shelter. Lynette said she would think about it. I also told her what Jeanette and I did and asked her how she knew about stroking and tit fucking. Lynette said probably because she has snuck around and seen her have sex with men. I told her we would have had sex but Jeanette did not want to do it in the hallway. I also told her Jeanette seemed hesitant about doing it in the apartment while she is there. Lynette said not to worry there will be a day very shortly where I can fuck Jeanette when she is gone. I told her Jeanette is a virgin. Lynette said she was not sure but suspected she still was.

The weekend ended and the next week of school started. In the same class as the assignment we had to have a partner for we had another of the same kind. It was actually the next stage of the assignment. Jeanette and I talked about it and planned to meet at her apartment over the weekend. She also told me she wanted to talk about we would also have more fun.

The weekend came and I called and went over to Jeanette’s apartment as planned, Lynette was not there.. I thought we would work on the project before talking. She wanted to talk first. She told me she really enjoyed what we did last time in the hallway and wanted to do more. She also told me her grandmother told her about what we did in the battered women’s shelter. Then she made me promise not to have sex with her grandmother while we were together. I told her if we do not do something soon I will be tempted and will likely fuck her grandmother. I also asked her if she made her grandmother promise the same thing. She said she did. I asked about other girls. She said she did not care about other girls we went to highschool with, just not her grandma.

We worked on and finished the project. We then started to make out. We kissed I had her top and bra off, she had me practically naked. She even let me take her jeans off. She laid back on her bed and helped put my hand down her panties. What I felt was incredible. She had a very hairy pussy for a teenager. I slipped my fingers between her pussy lips and felt a very sticky wetness. At first I thought it was vaseline or some other kind of lubricant. I told her you do not have to use so much and usually it is used on the guy,not the girls pussy. She said it is not anything like that, but that it is her own natural fluids when her pussy gets excited and aroused. I kept massaging her pussy and tried to slip a finger in her love tunnel but she stopped me. She said she was not ready yet. She switched positions with me. I thought she was going to tit fuck me again. Instead she gave me a blow job. I was her very first. She was very good despite having no experience. When I got close I told her I am about to cum. She quickly switched to tit fucking me and said I want a “pearl necklace”. As I started cumming she moved her chest to my cock so my cum would splash all over her next and run down between her tits.

I could tell she wanted to get off. To her surprise I got up, quickly had her lye back, took off her panties, she again said not yet. I told her not to worry I am not going to fuck you until you tell me when. I spread her legs and started eating her out. Her thick creamy pussy juice tasted better than I imagined. It was very sweet and thick. She had one explosive orgasm after another. When she was done I got up, we got dressed and I left.

On the way out I passed Lynette in the hallway. I stopped and talked with her. I told her what just happened. She told me she was with my mom and they had sex. We also talked about the promise to not fuck each other and that I could fuck other girls around my own age and asked if she knew of anyone. She said yes, Jeanette’s cousin Jenny. I said I know Jenny and had some classes with her. She said Jenny does not look like it but likes to fuck pretty much anything with a pulse and a cock and would be an easy lay for me until Jeanette lets me fuck her pussy. She gave me Jenny’s number and I left. I planned on calling Jenny the next day, Sunday.

After church on Sunday when I got back home I called Jenny. I told her her grandmother, Lynette gave me her number and that I should call because she thought we could be friends. Jenny said she knew who I was and asked if I wanted to come over to her place. She said her parents were not there but her younger sister was. I went over. When I got there Jenny and her little sister Marcia were having an argument. It was something about that Jenny was not supposed to have boys over and was going to tell mom and dad and Marcia knew what Jenny and boys were doing in her room. At the time Jenny and I were both 16 and Marcia was about 13. Jenny called Marcia a jealous virgin and Marcia called Jenny a slut. Jenny slapped marcia and she started crying. I told them both to calm down and things are OK. Marcia asked when will it be her turn. I asked Jenny what she meant, she said Marcia wants to have sex with a guy but was still too young. Marcia asked if she could watch Jenny and I. Jenny asked me if it was OK. I said sure. We went to Jenny’s room and started making out while Marcia watched. Jenny was nice and slender with big tits. We were kissing and feeling each other while we took each others clothes off. I sat on her bed and she got on her knees and started sucking my cock. I looked over at Marcia who was laying back and rubbing her pussy through her pants. I stopped Jenny because I did not want to cum in her mouth,I wanted to give it all to her pussy. She got on the bed on all fours and presented her pussy to me from behind. I got behind her and shoved my cock deep in her pussy and fucked her hard and fast. While I was fucking her I looked over at Marcia. She had her shirt and bra off and her pants off and only had panties on. She had one hand in her panties and the other massaging her tits. I noticed her tits were bigger than Jenny’s even though she was younger. This sent me over the edge, I pushed Jenny’s head lower into the pillow so her ass and hips would be higher, I grabbed her hips and fucked even harder and then came my entire load in her. I then heard Marcia moan while she gave herself an orgasm. Jenny was so exhausted she fell forward with her legs apart and my cum leaking out of her onto the bed. I said thank you baby, you’re an awesome fuck. Got up, got dressed and left.

The next day at school Jeanette approached me and said she knows what I did with Jenny and that Marcia was there too. I told her if you would let me fuck you I would not have to fuck anyone else. I also told her Marcia wants to have sex and I am tempted to fuck her first before I fuck you. This made her mad and jealous. She did not talk to me for a few days after that.

That Friday she said she wanted me to come over on Saturday and that she was not mad anymore. I asked her why,we didn’t have any assignments to work on and she was not going to let me fuck her an I wanted more than just a blow job and tit fuck. She said she talked to Jenny about it and Jenny convinced her to let me fuck her. She also told me her grandmother was not going to be home.

I went to her apartment on Saturday. When Lynette answered the door I was surprised and said I thought you were not going to be home. She told me not to worry about it and told Jeanette and I to have fun. We went into Jeanette’s room but had to leave the door open. It was Lynette’s rule when Jeanette had friends visiting. I knew it was more like Lynette wanted to watch and hear us have sex.Thankfully Jeanette’s bed was around the corner in her room from the door. We immediately started making out. She wasted no time in taking her clothes off, then mine. I had only seen her completely naked one other time and it was not for very long. She laid back and spread her legs and asked me to be gentle with her. I could see her virgin hole open up to me. I laid down between her legs and started kissing up her calves and thighs while massaging her pussy. I wanted her to enjoy it because I knew she was very tight and it was going to be painful once I got my cock in her. I kissed and licked around the outside of her pussy taking in her sweet innocent scent. She was very wet with her natural thick wetness. I lapped up as much as I could while shoving my tongue as deep into her tight hole as I could. I applied more and more pressure with my tongue and lips. She was moaning and I added my fingers along with my tongue. As I tried to stick a finger in her she cried out and told me to stop.

I stopped and moved up and put my chest against her tits and started kissing and sucking her tits, neck and mouth. I reached down and guided my cock to her pussy hole. I was very hard and tried penetrating into her. I could feel her tight opening almost give way but she cried out in pain again. So I stopped and backed off. I looked into her eyes and she smiled and said she really wanted it, she wanted to feel what her cousin Jenny felt in her pussy. She spread her legs wider and lifted her pelvis up a little more toward my cock I got on my knees and placed my hard cock in between her pussy lips and started rubbing along the lips. She was really wet and having an intense orgasm because I was rubbing directly on her clit. As she was cumming I took the opportunity and shoved my cock into her tight hole. With one big thrust. She cried out but told me not to stop. After I got all the way in her she told me to hold still so she could get used to my size. She also said Jenny was right, I am huge and it feels great. After a few moments I started humping in and out of her. She started moaning and moving with me. I knew I was not going to last long and came inside her tight pussy. She orgasmed at the same time and I felt her pussy muscles milk my cock dry. It was so intense we were both sweating and breathing hard. I collapsed on to her chest and we lay there enjoying the moment. I heard a noise and looked toward her door and saw Lynette pull her hand out from under her skirt and duck out of the door. I told her that her grandmother was watching us and was fingering her pussy. Jeanette said I know because she saw her there earlier right when I was eating her out.

We got up and got out of her bed. As we were getting dressed she said she did not want me fucking Jenny anymore because she would give me all the pussy I wanted. I agreed.
For the rest of the school year we would get together and fucked at least once a week. Sometimes it was at her apartment, other times it was at my house. We even fucked at my church, where I first fucked Faith. We even fucked in the prop room behind the stage of our high school auditorium during a school day. There was one day on the way home from school i the winter time we could not wait until we got back to her apartment and my mom was home at my house. We went down a bike trail near our high school that ran along the river. We went down on the bank, made a spot in the snow. We made a blanket out of our coats. We pulled our pants down she laid down, spread her legs and we started fucking. We think someone saw us who was walking on the trail. We do not know if they saw us go down there, or saw our tracks and followed them where they went into the trees. I looked up and saw two adults trying to look into the trees to see who was down there and where we were. We stopped fucking and got quiet. I told Jeanette what was going on. Jeanette smiled at me and said let’s give them a show. She rolled me over and started to ride me on top with her huge tits bouncing up and down on her chest. She then started to moan very loudly on purpose. She normally did not moan like that, this was intentional to get their attention. They kept trying to see where we were. We heard one of them say let’s go down there. The other one said no we do not have the shoes for it. As Jeanette was moaning and bouncing on my cock with her tits flopping around I got even more turned me on even more and I intentionally announced I am going to cum. All of a sudden I started to cum deep in Jeanette’s pussy she yelled out in pleasure even more. She fell forward onto my chest out of breath. We lay there quiet for a little while until the other two people left. We know they never saw us, even though Jeanette tried to get them to.

We also fucked under the bleachers at high school football games and even in empty area during basketball games. We actually managed to fuck each other in each high school in the city during basketball games when our team played others on their home court. This included the Catholic high school. As the weather warmed up and the snow melted we would meet and fuck in the baseball field dugout when there was no practice or games.

The school year ended and we kept finding places to fuck each other as much as we could. One day she told me she got accepted to a program for potential college students and was going away for the summer to participate in it. She said she wanted to do a threesome with me and Jenny before she left but wanted it to be at my house.

I had to start thinking about a way to make that happen. It was one thing to either sneak Jeanette into my mom big house, fuck her in my bedroom or somewhere else on the property and then sneak her out if my mom was home. It was also one thing to just simply have Jeanette come over when my mom was not home so we could fuck, which did not happen very often. It was something else entirely to bring two girls to my house to fuck at the same time. For one it would have to be planned when I knew my mom was not going to be home. I also knew fucking two of them would take longer than fucking just one. At this point my mom knew about Jeanette and I. I knew Lynette had told her about me having sex with her granddaughter. Lynette had told me she told my mom, but my mom did not know that I knew. My mom knew of Jeanette from me because of the school projects we had worked on, but that was it.

One night my mom told me she needed to talk to me. I knew I was not in trouble, but also knew it was serious and important. She sat down with me and told me she knew I was sexually active and it was with Jeanette. She asked me if I had any questions about sex. I asked her how she knew. She told me she was friends with Jeanette’s grandmother, Lynette. I said I know about her friendship with Lynette. She asked me how much I knew. I decided to tell her I knew they had lesbian sex together and then told her I had sex with Lynette in the past when we were at the shelter. My mom said she was wondering who’s cum she was eating out of Lynette’s pussy. I also told her I enjoyed kissing Lynette’s lips after she had eaten her pussy out and loved the taste. I also told her I am happy for her and that she has a enjoyable sex life and she deserves it. She told me the same. I then told my mom about sneaking Jeanette up to my room or bringing her over when she was not home to have sex with her. She told me I was not as sneaky as I thought and she knew. She said it is OK and that all teenage boys need a girlfriend to have sex with as long as they respect her she did not want a son of hers disrespecting any girl or woman he had sex with. I knew what she meant and did not need to ask questions. I assured her I did. I then told her about Jeanette going away and us wanting to have one more sex encounter before she left. I also told her about Jenny and that Jeanette wanted her to join us and she wants it to be at the house. My mom asked me when we want to do this. I told her whenever we could be alone and before Jeanette left. My mom said to let her think about it and she would tell me in a day or two.

The next day I called Jeanette and told her I am working on a day for her and Jenny to come over and it would be soon. She said she will call and let Jenny know. I told her I will call them both in a day or so to let them know.

A couple of days later my mom told me she is OK with me, Jeanette and Jenny having sex in my room, but she wanted to be in the house and would make herself scarce so they do not know she is there when they get to the house, while we are having sex and when they leave. She also said Lynette will be there too. I asked if that meant what I thought it meant. She smiled and said yes. At that point I thought it her and Lynette would just have sex with each other and not with a man before. My mom then told me she was going to have sex with a guy before Lynette comes over and Lynette wanted to have sex with me before I am with Jeanette and Jenny. I then told her about my promise to Jeanette about not having sex with Lynette while we were together. My mo said it will be up to me to make sure Jeanette does not find out about it and Lynette will do the same. She then told me the day we could do this. We talked about this on Wednesday night, the day for having sex was to be the coming Sunday. My mom left it up to me on how to fuck Lynette and fill her pussy with cum before they had sex and before Jeanette, Jenny and I had sex. She did tell me she was not going to make me go to church with her.

I had to call Jeanette and Jenny the next day so I had to come up with a plan to fuck Lynette before her and my mom were to have sex without Jeanette knowing about it. I knew my mom would be at church that morning and Lynette was supposed to be there shortly after she got home. I called Lynette’s phone number, expecting to talk to Jeanette. I was going to ask to speak with her grandmother after I told Jeanette what time I need her and Jenny at my house. Lynette answered and I asked for Jeanette. She told me she was not there, she was at Jenny’s. I told Lynette what my mom and I discussed and that she wants us to have sex before they had sex together. I told her to come to my house right after my mom left for church so we could fuck before my mom got back and before Jeanette and Jenny got there. Lynette agreed. I then called Jenny’s phone number and told her and Jeanette what time to be at my house on Sunday.

Sunday came, my mom left for church and Lynette came over, At first I wanted to fuck her in ny bedroom. She said we should not because Jeanette may figure out we had sex because of the cum that would leak out of her pussy all over my bed. She said let’s have sex in my moms bed it will make her really horny when she finds out her son and best friend fucked on her bed. We went to my mom’s room, took our clothes off and started making out. We got in the 69 position. She edged me and I ate her fat pussy out. She did not want me to cum too many times so I had enough to fuck Jeanette and Jenny. After I got her pussy good and ready she got off of me and had me lay on my back. She reached over and got a dildo out of my mom’s night stand and then sat on my taking my cock deep in her fat pussy. She told me not to move, she wanted to let her pussy massage my cock and milk the cum out of my balls. I just stayed still with my cock deep inside of her. I felt her pussy pulsing and massaging and milking my cock. She kept getting tighter and tighter around my cock. I had never felt anything like that. It was all because she was massaging her clit and outer pussy lips with my moms dildo. All of a sudden I could not hold back any more and filled her pussy full of cum. She collapsed on top of me and started sucking her tits and kissing her. She could feel me getting hard in her pussy again but told me I had to wait until Jeanette and Jenny got there so I could fuck them.

She got off of me and my cum started leaking out of her pussy. She grabbed one of my moms pillows and started rubbing her pussy on it. She told me it was to spread our scent so my mom could smell and lay in it when they had sex. She then laid on her back and put my moms dildo deep in her pussy. I asked her why and she said to keep my cim inside of her for my mom to eat out. She told me to go clean my cock off so Jeanette does not find out. I went to the bathroom and washed myself off.

No sooner had I done that when Jeanette and Jenny knocked on the front door. I answered the door and took them upstairs to my bed room. They had to use the upstairs bathroom. When they were doing that I heard my mom come home. I went downstairs and heard her and Lynette in her bedroom. I heard my mom say it smelled like sex. Lynette told her she had just fucked her son in that room and I am upstairs with Jeanette and Jenny. I heard Jeanette and Jenny call my name and ran back upstairs. I found them naked in my bed with Jeanette eating Jenny out. Jeanette’s was on her knees with her head between Jenny’s legs. I got naked and shoved my cock in Jeanette’s pussy from behind. Jeanette was not expecting it and cried out in pleasure. As I slammed her fat ass from behind it sent ripples through her body and her huge tits flailed out to the sides of her chest. I could feel her thick, natural wetness ooze out of her pussy, run down my cock and coat my balls. Because I had fucked and cum in Lynette it took me a bit to cum in her granddaughter. Jeanette knew it took me longer to cum when I fucked her from behind which is why I wanted to fuck her like that to start with so she would not suspect I had sex before I started fucking her. She soon wanted my cum in her pussy. She arched her back, and put her head lower for me which changed the angle of her pussy hole and caused me to cum deep and hard in her fat pussy. Jenny also came from Jeanette eating her out.

I pulled my cock out of Jeanette and laid back on the bed. Jeanette got off of Jenny and laid back on my other side, I was between both of them. My hand found its way to Jenny’s pussy. Nd her hand started stroking my cock. She got me hard but wanted to suck me first. She sucked Jeanettes thick pussy juices off of my cock. After she had me really hard she lay on her back and spread her legs wide. I got between her legs and plunged my cock into her pussy. Jeny then wanted Jeanette, who was fingering herself, to sit on her face so she could eat her out. Jeanette squatted over Jenny’s face. Jenny started eating Jeannette’s pussy while she held Jenny’s legs up for me so I could fuck Jenny while on my knees. Jeanette started to have her orgasm from Jenny eating her out, Jenny started to orgasm which made me cum deep in Jenny’s pussy.

After we were done I got out from between Jenny’s legs and Jeanette let her legs go but laid forward to eat Jenny out in 69 position. They were both eating my cum out of each others pussies. I got dressed and went downstairs. My mom and Lynette were coming out my moms bedroom. Both looked like they had a great time and apparently they thought the same of me. My mom grabbed me and gave me a big motherly hug, Lynette joined us and started kissing me with tongue. Lynette then left so she could get home before Jeanette. My mom asked what Jeanette and Jenny were doing. I told her. She told me if either one were 18 or older she would try to have sex with them. I asked her why it made a difference when Lynette and I had sex that I consented to. She really did not give me an answer.

We heard Jeanette and Jenny come out of my room to head downstairs. My mom went and stayed in her room until they were gone. After they left she came out of her room. I went to bed early that night because I was very tired. A few days later Jeanette left.

Jenny and I continued to have hot sex over the rest of the summer. Her virgin sister Marcia kept trying to get me to have sex with her which pissed Jenny off. It got to the point where we had to have sex anywhere but their house.

Summer ended and school started again. I did not see Jeanette. I called Lynette to find out what happened. She told me she transferred to another school for certain classes she wanted to take. I know I will never forget deflowering Jeanette.

I continued to have sex with other girls but never had sex with Lynette again after the last time in my house. I did fuck Jeanette one more time several years later but not until after I fucked and deflowered her cousin Marcia. That story is next.

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