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Amy Tale/s – High School Football Virgin

2602 Words | 2 |5.00

…he is going to realize how mature I was when he lost his cherry; and how inadequate his dick was in my pussy, and he will never forget that.

I am at work one Friday and Janet shows up dressed casual in a skirt and top and her patented open toed high heels, and it was close to 3pm. She was walking toward me and talking on her phone. She hung up when she reached me and said, come on girlfriend we are leaving, I have stuff to do. I said, excuse me girlfriend, but I have 2 more hours of work. Janet told me she called Ken, and that Ken was feeding the store manager some bullshit about me having to leave early. I found the store manager, and echoed what Janet told me, and we left.

I said, where are we going? Janet said, to a high school football game. Now? Janet said, no silly, it starts tonight at 7pm, we need to prepare for what comes after. We went to Ken’s apartment, and as soon as we got there, someone delivered some really good takeout food. Janet brought a bag in, and she stripped me, and we showered. She washed the shit out of me, and she douched us in the shower, and after we did our hair and makeup. Janet fumbled through my closet and dressed me in a skirt and warm top. I had my bra on, but she would not let me put panties on. Janet dressed normal for her in a skirt and warm top, we both had calf high boots on, and Janet had no bra and no panties.

Janet packed me a bag, and she grabbed my coat and we left. Janet took us to the Resort. Just FYI, when I say Resort, I mean a really expensive inn. The kind of inns Ken and Janet take me to have single or double names and hotel or inn were not in the titles. Janet went up to the desk and said she needed her key. A bellhop came over and took our bags, and he led us up to the top, to a suite. It was a one bed suite, but with all the amenities and supplies. Janet tipped the guy, and we talked and communed around for a bit, and it was about 6:45pm, and Janet said, let’s go.

We arrived at the high school, and Janet had a blanket and a carrying a coat too, and we went in. Janet bought some popcorn and drinks. We sat on the bottom bleacher right in front of the cheerleaders, after Janet folded the blanket for a place to sit. Good news is, there were not many people sitting right next to or behind us. It was hard to see the field for the cheerleaders and the football players standing on the sideline, so we really did not watch the game.

The game had started before we sat down, and after a bit, these cheerleaders were jumping around and doing their cheers. Janet was sitting with her legs crossed, eating one piece of popcorn spaced out over a minute in between, and she was staring at the cheerleaders. Then Janet leaned forward and rested her left elbow on her thigh holding her chin in her hand. Janet reached over with her hand inside my thigh, and she spread my legs and rubbed the inside of my thigh. I don’t think you could see my pussy for the way my skirt was laying, but some of the cheerleaders were watching what Janet was doing; and Janet was staring them in the eye. I was just glancing at them and at Janet, and around like I was trying to see the game.

Janet was fucking with these cheerleaders. We looked like a mother and daughter at a football game that little Tommy (a hypothetical son and brother to us) was playing in. Okay, the cheerleaders might have thought, Janet is just being affectionate with her mom, and rubbing her leg because she is cold. The cheerleaders got to hooting and hollering again, and Janet moved her hand up (which moved my skirt), and Janet began rubbing my exposed hairy pussy. These fucking cheerleaders could not focus on their cheers, but they tried. When they stopped for a bit, some of them were whispering in the other’s ear, and watching Janet play with my hairy pussy. I wanted to stop Janet, but so far, only the cheerleaders had noticed.

Janet kept fucking with them and rubbing my pussy, and some of the cheerleaders had walked around behind the players standing on the sideline, and now some of them were looking. I started looking around feeling embarrassed, and I noticed people behind us and further down on the bleaches were looking at us every now and then, probably trying to figure out what the football players were looking at. Janet was sitting real close to me, so I know the people in the bleachers could not see.

Pretty soon, students were walking by in front of us and looking, and when I saw them approaching, I would close my legs. Janet would manage to get my legs spread again, and she started actually fingering my pussy. It began to feel good, and I was anxious and nervous with butterflies in my stomach from the thrill of such a public act. Some boys walked by and I closed my legs. Janet said, hey boys, you got a second; and they walked over? Janet asked, are either one of you a cherry boy? Of course, they did not answer, what boy is going to admit he is a virgin, and they walked off. I said, what are you doing? Janet said, looking for a virgin.

Janet would go back to fingering me, the cheerleaders and some of players would watch (gossip spread), more students would walk by; and Janet would engage them in a conversation trying to get them to admit they were virgins. In today’s high schools, it’s hard to find a virgin with all the alternative lifestyles. Janet got some of them to say they were virgins, but they did not look like virgins. It seemed more like they were flipping the table on Janet in order to hook up.

Janet finally got some skinny white boy to admit he had at least never had sex with a girl (and probably not a boy either). He was average looking and with another friend, but he was a young boy. I am going to say this for the readers and host of this forum, you can be 18, and in high school…wink. Janet asked the boy; will mommy and daddy miss you if you leave? He said, I am staying with “Billy” tonight, and he glanced at his friend. Janet said, what if you don’t go home with Billy, will you get in trouble? They did not answer, and they conferred among themselves. He answered back, me and Billy can say we are going to “Johnny’s” after the game.

Janet said, how about Billy goes to Johnny’s, and you come with me, and I will fuck your brains out? They looked astonished, and they conferred again, and both wanted to come. Janet said this was for the virgin only, and Billy had already admitted he was not a virgin. They talked some more, and “Tommy” finally said, yes, he would leave. Janet said, meet us at the gate in 10 minutes and they left. Janet waited a bit, then said, let’s go. We gathered our things and went out the gate, and Tommy was already there. Janet took us back to the Resort.

Janet undressed me, as only Janet can do so sensually, and Tommy sat on the bed watching. This little boy was in for a night he would never forget. I was naked, and I was standing in front of Tommy with my double D soft tits and hairy pussy available for his viewing pleasure. Janet got naked and rubbed me, and she watched little Tommy choke on his own spit. Janet walked over to the bar and reached in the fridge, and she got little Tommy a drink. Janet then went back to rubbing me. Janet stood behind me and rubbed my breasts, and she fingered my pussy. I was wet, and excited more by Janet and her games, than little Tommy.

Janet went over to little Tommy, walking as she does, and showing him her perfect swimsuit model body with the smooth pussy, tight ass, and firm C tits and lovely nipples; and she took Tommy by the hand. As Janet passed me, she took my hand too, and led us to the bathroom. Janet put our hair in a ponytail as little Tommy watched Janet move around my naked body. Janet looked at me and said, help me undress Tommy for a shower. We undressed him, and his little less than 6” circumcised pecker was rock hard, and it was touching his stomach. I mean damn, his little dick was cute as hell. To be honest, looking his little rock-hard pecker, sparse hair (not even growing on his little ball sack), and the way his dick was standing straight up against his stomach, made you want to suck the shit out of it.

Janet led the three of us into the big shower that was separate from the tub, and Janet and I stood on each side of Tommy. Janet rubbed on little Tommy, and she rubbed his balls and dick with her hand flat. Janet took my hand and we both rubbed little Tommy’s dick, and we kissed on his ears and neck. I started jacking on little Tommy’s dick slow, and I was thinking, he is so small, but it was turning me on playing with this little developing dick. I wasn’t going fast, and little Tommy shot a load of cum out like a water pistol, and I squeezed his little pecker as I stroked, and more cum came out and ran down my hand.

Janet says, better in here than out there, Tommy. We got out and Janet led us to the bed and brought towels. Janet laid little Tommy down and she sucked on his dick and pulled me in, and we took turns. Little Tommy was almost hard again before we hit the bed from the shower. I started licking Tommy’s modest ball sack, and Janet got serious sucking his dick. Little Tommy, got off again, and Janet swallowed his cum. Only my brother had ever cum in my mouth, and I spit it back on him. It did not take Tommy long to start getting hard again, as we kissed and licked on his dick and balls. Janet started sucking him purposefully again, and little Tommy was rock hard.

Janet wanted me to suck his dick and make him cum in my mouth, but I did not want to. She kept pressing me until I sucked little Tommy’s dick. I sucked, and Janet spread her ass over little Tommy’s face and said, lick my pussy little boy, and Tommy started licking. Janet leaned over and started pushing my head down on little Tommy’s dick. I have a gag reflex, but I was amazed at how much of Tommy’s little pecker was in my mouth before it caused me to gag. I sucked his little dick, and it took longer this time, not just because it was Tommy’s third ejaculation, but because he was trying to eat Janet’s pussy too.

I sucked that little dick, and Tommy got off in my mouth, and I swallowed it. It was salty, and I did not smell it, but I had a smell in the back of my nose that was like swallowing pool water accidentally. Fortunately, this was his third ejaculation, and wasn’t near as much as came out in the shower. Janet moved her pussy off Tommy’s face, and looked at Tommy and said, this is how you eat pussy. Janet rolled me onto my back, and we got in a 69, and Janet started eating the shit out of my pussy, and I did the same to her pussy. I got off first, and when I was done, I completed my efforts on Janet, and she orgasmed too. This took about 10 or 15 minutes, and it provided Tommy an example of not only how to eat pussy, but what a woman does when she orgasms.

Janet looked at little Tommy and said, you ready to fuck your first pussy? He shook his head, yes, enthusiastically. Janet pulled little Tommy between my legs with me on my back, and she guided his little dick into my wet pussy. Little Tommy started fucking me with ease. Now, I could barely feel his little dick, and to this boy, he probably thought it felt great, and was warm, soft, and wet, and he could feel me around his dick. He will remember this night, but in years to come, when he fucks some little tight pussy, he is going to realize how mature I was when he lost his cherry; and how inadequate his dick was in my pussy, and he will never forget that.

Janet pushed little Tommy down on my breasts, and he took hold of my soft supple mature bosoms, and he rubbed, kissed, licked, and sucked my nipples. This too will never escape little Tommy’s mind as long as he lives. He will fondle some teenage girl soon, and her firm rack will feel nothing like my ample and soft breasts, and he will forever be trying to find such breasts for the rest of his life. I pull little Tommy’s face up, and I kiss him long, passionately, and deep, and I push him back to my tits and he continues to enjoy them.

I wrap my legs around little Tommy and grab his ass with both hands and move my hips to enhance his experience. He is breathing heavy and thrusting harder, and I move his ass around to stir my pussy with his little magic wand. Little Tommy gets faster laying on my breasts and holding my side tightly, and I ram his ass into my pussy and little Tommy cums, and I squeeze his ass and force him as deep as he can go. I hold him there while he respires and shakes on my breasts. I don’t let go, but I hold him tightly in my pussy using my feet and hands on his ass. I relax still keeping his little dick in my pussy and I rub his back with one hand and hold him to my bosom. After a few minutes, I can tell that what I did feel of his little dick in my pussy, was fading away.

Janet says, did you like that Tommy? He just nods his head, yes. It is after 11pm, and Janet tells little Tommy that she needs to take him wherever he needs to go. We get dressed and I ride along. Tommy had called his friend Billy, and we dropped him off at Johnny’s house where the two of them let Tommy in. Janet and I returned and spent the night at the Resort, and we fooled around. We mostly giggled about what we just did, and how that boy would never have such an experience as that, for the rest of his life. Janet and her games keep things interesting. Maybe one of the cheerleaders that saw us talk to little Tommy will be his second adventure. Who knows?

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  • Reply Maxdefault

    Thanks for commenting. If you have ideas for my new fantasy series, let me know.

  • Reply 69jose

    Wow this story made me hard! Great story, would love to chat.