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High School Memories Ffm Anal

My name is Jake and I wanted to share some of my sexcapades so let's take a stroll down memory lane. I always knew I had something special. I played high school basketball and you couldn't help but noticed the other guys equipment in the showers and mine was usually the largest. My package when angry is nearly 9 inches long and pretty thick. I sometimes hear the other guy whispering comments about my dick but I would really like to have listened in on what the girls had to say. Believe me girls talk much more than guys do and I had no problems getting girls back then.

One of the first girls I dated was Donna, no she wasn't a cheerleader but she was part of the pep club. In fact she was one of the officers and they all were at the games cheering us on. She was totally bossy but she was very cute brunette and had a huge rack. Some of the girls in high school had those adolescent titties but not Donna. She had full grown voluptuous women breasts and I should know I came on them dozens of times. If we didn't have a condom available I would have to pull out and she would let me cum on her tits. I wanted to cum in her mouth but she wouldn't have any of that. "No one cums in my mouth." she stated time and again. One weekend at her house we had the place to ourselves and we were doing the nasty in her room. I have to admit Donna knew how to fuck. She would suck my cock like a pro and then she would have me fuck her missionary as she screamed her head off. "Yeah, fuck me hard, make me cum." she yelled. She was one of the few girls who could handle my thick cock and she loved the way it filled her up. I enjoyed fucking the shit out of her even if she ordered me around even in the bedroom. In the midst of her orgasmic joy she would say, "Good, good...be sure not to cum inside me." I forgot to bring a rubber that day and even when she was close to climax, she would still remind me. She let loose soon after and her entire body shook as she cried out, "Fuuccckkk!" I was right behind her and I slammed my cock as deep as I could a couple more times and pulled it out of her spasming cunt. Usually she would grab the base of my shaft and stroke it until I finished spurting spunk all over those creamy white orbs. But she was in her ending throes and she wasn't concerned with my needs. I was straddling her chest but she absorbed in her own climax. I could have done myself but I didn't want to jack off. I could and did do that enough back in high school. "Donna!" I cried. She looked at me if as through a haze. By the time her hand encircled the base of my shaft, my urge had passed. She jacked me off for a while and then the bitch told me to hurry up and cum. I told her that I had lost it and asked her to help me out, "Suck it, baby." "It's nasty." she replied. Donna had never sucked my cock once it had been in her pussy. "Please." I begged. She begrudgingly agreed but told me, "You better be sure to pull out before you cum." She began to suck me again and knowing she was doing her first cunt to mouth definitely got me going. She kept stroking the shaft of my cock as she could only get half of my cock into her mouth. I felt that old familiar feeling returning to my loins and my cum began to boil over. I guess I was shoving more of my cock down her throat and I heard her garble, " Tel e when ur goin kum." I wanted to feel at least once her sucking my dick as I pumped sperm down the length of my shaft. This selfish bitch did really deserve it so I said nothing as my load exploded into the back of her throat. Her eyes got so big and she screamed as best as she could with my thick cock stuffed in her mouth. I forced more of my cock into her mouth. My release was sweet and I poured stream after stream down her throat. With her head so close to the mattress she couldn't back away and the massive load I was pumping was going to drown her if she didn't swallow. She finally relented and I felt her sucking my gism down. I kept cumming and gave her a protein milkshake that she would never forget. I came for a long time and when I finished I yanked the sensitive head our of her mouth. "You bastard!" she shrieked. I rolled off the bed and got dressed as she continued yelling obscenities in my direction. As I hit the bedroom door she screamed, "You will never cum in me again." I chuckled to myself, 'I just did.' Needless to say, Donna and I stopped dating after that day.

A couple weeks later football season ended. The team had their usually blow out bash and a lot of the basketball team attended. Donna was there with some of her friends but we never said a word to each other that night. Now let me tell you about Tara. Tara was a cheerleader. She was a platinum blonde with a great athletic figure. She was always voted most popular every year and our senior year she was the homecoming Queen. They say cheerleaders are very promiscuous but that wasn't the case here. Tara had been only dating Todd for the last two years and he was of course the starting QB of the team. Todd was really tieing one on and toward the end of the night he was passed out in his room since the party was at his place. I don't know why I hung around til the very end because I didn't have any prospects lined up that evening. But Tara caught me as I was one of the last ones to leave and asked me to help with some cleaning up. She asked me to check out Todd's parents bedroom in case somebody had left something in there and I wasn't in the room for more than a minute before she came in also and locked the door behind her. She walked up to me and placed her purse on the bed. She simply said, "Todd's passed out cold." She then put her hand on my crotch and squeezed my soft dick and said, "Nice one." I don't know if one of the girls told her about me but she was definitely interested in my package. She told me she wanted to see it and proceeded to pull off my pants. She dropped down on her knees in front of me. I let her and when she pulled down my underwear, I thought I heard her let out a small gasp. She said nothing but just grasped it and gently caressed it before looking up at me and stated, "It's so nice and big." She started kissing it. It grew quickly and she took it into her mouth and her head began to bob back and forth. I couldn't believe I was getting head from the head cheerleader. I savored the blow job this hot vixen was giving me. When I was good and hard she stood up and began to undress, "Take your clothes off." is all she said. She shed her clothes also and her body was heavenly. Her breast were ample, her ass was round and supple, and her pussy was covered with feathery yellow pubes. Pubes wasn't the right word, down would be a better description. She asked me if I had a rubber and I told her I didn't but she just asked me not to cum inside her pussy. She laid down on the bed and spread her cheerleader legs wide and told me, "I want you to fuck me now." I scampered up between her thighs and rubbed my saliva coated cock up and down her slit. I could feel her pussy was already slick, wet and ready and when I pushed forward her vaginal lips enveloped my cock. She let out a loud sigh as my cock continued its' journey into her forbidden depths, "Aaahhh." As wet as she was her cunt was still tight but it was especially warm and so sweet. It took all my concentration to pumped her slowly and gently. This girl must have been thinking about getting some huge cock all night because she was cumming in no time. I'm pretty sure she had never experience such a large cock as mine and she was loving it. She sounded like a puppy whimpering as she climaxed, "Ouh, ouh, ooouuhhh." It was freaking hot watching her wiggle and squirm with my huge cock embedded in her cunt. When she recovered she asked me to fuck her some more. She got on her hands and knees and wanted it from behind. I mounted her and fucked her harder this time. "Oh, you're filling my pussy so good." she moaned. She was totally enjoying the pounding I was giving her. Tara said, "If you're going to cum, ugh.. ugh..you can cum in my ugh..ugh..ass, I have some lube in my purse." UNBELIEVABLE! She was offering her ass to me. When I got over the shock, I thought it was kind of funny how she didn't have any condoms in her purse but she did have lube. I guess good girls don't carry protection in there purse only anal eaze to accommodate large cocks up their asses. This girl was hot and she began to shove her ass back against me as I fucked her. "Fuck me harder!" she cried. Harder... I was close to blowing too but I wanted a crack at her ass. With my package no girl had ever offered to let me ass fuck them and I wanted Miss Most Popular to be the first. I tried to think of something else but being a teenager I had no control. I finally grabbed the base of my cock and squeezed it hard. That definitely put off the feeling I was going to explode and she soon kept shoving her ass against me and came again. When she stopped whimpering she collapse face down on the pillow. I pulled my dick out and she kept her ass up for me. I took the bottle of lube from her purse. I pretty much used up all of it covering my thick cock as the bottle was only half full. Todd, you lucky bastard. As I lathered up my big boy I couldn't take my eyes off her backside. Her bubble butt was round and inviting. Her pink button was perched on top of her vaginal slit. Her cunt was gaped and her lips were puffy and slick having been recently fucked hard but her asshole was still pristine and tight. This was the homecoming Queen's ass and it wanted my cock to fuck it. I could have jacked off just looking at it. I moved closer to her and put one hand at the top of her butt and used my right hand to guide the head of my cock against her tightest hole. I wanted my cock inside her ass more than anything. My enormous cock head was more than 20 times as large as her little anal opening and I shoved it against her but nothing happened. It wasn't making any headway. Tara reached her hands back and pulled her ass cheeks apart. I saw the slightest crack of an opening appear and I tried again. It was the most amazing thing I'd ever seen as the head of my cock eased into her butt. It was extremely tight but felt so smooth and wonderful. Her tiny asshole expanded around my cock until eventually the ridges disappeared. She let out a little squeal as her sphincter clamped down on the head of my dick. She just pulled her ass apart some more. I pushed again and it took a bit of an effort shoving my cock into her tight little ass as she gasped, "Ughhh!" I asked her if she was OK and she told me she was but, "It was bigger than I thought." I was gentle with her and soon I had at least five inches in her. "Is it almost all in?" she groaned. I lied and told her almost but I did have enough in her to start a nice pace as I slid my thick cock in and out of her tight ass. This wasn't going to take long as excited as I was. I was not only fucking my first piece of ass but I was fucking the hottest piece of ass in the whole school and I wanted to fuck her for a long time. But my pace picked up and she sensed I was close and groaned, "Cum baby." She continued laying face down and even spread her ass wider to accommodate me. Picture this, five digits 2 or 3 inches on either side of the crack of her ass pulling her cheeks apart, my thick cock going in and out pulling her anal ring back and forth as it slid along my veined engorged shaft. It was taboo, it was perverted and I sodomized the shit out of her. No way I was going to last very long. I pounded her several more times and with my final thrust I shoved all 9 inches up her ass. We both yelled out at about the same time as my cock squirted white hot cum into her butt, "Uuuugghhhh! Aaarrgghhh!" My shaft pulsed as wave after wave of man seed filled her ass. It had to be the biggest load of my life up until that point. "Oh baby, it's so warm." she cooed. I don't know how long I pumped semen into her but when my stream started to slow down I backed off and fucked her butt a couple of more times and a new surge of cum arrived and I shot some more. "Oh baby," she exclaimed. I finally collapsed on top of her as I wound down with my cock still buried balls deep. My cock twitched weakly and the last few remnants of sperm left in my balls entered her bowels and then I was done. I was content that her ass was completely flooded when I finally finished. I lay on top of her without pulling my dick out and could have stayed that way all night but Tara told me she felt like she needed to use the bathroom. Pulling my cock out of her ass was one of the hardest things I ever had to do. She ran to the toilet and after about a minute she yelled, "OMG, Jake look what you've done." I wasn't sure what she meant but I went in to see. She had a white stream of cum dribbling out of her ass. It looked so surreal as that white load pour out of her butthole. She stayed on the toilet for another couple of minutes until only long strands were hanging out and finally breaking off and dropping into the bowl. She got up and flushed and I returned to the bed. I heard her cleaning up and she returned and set down next to me. I asked her if everything was all right and she said, "Yeah but do you always cum that much. " I smiled and said, "Always." She thanked me and kissed me deeply and told me how wonderful my cock was. She squeezed my placid cock one last time and then told me that I had better leave. I wondered if we would get together again but it turned out that wasn't to be. She's married now but at reunions she still gives me that 'cat that ate the canary'. I'll never forget my first ass fuck from Tara as long as I live.

Now my fondest memories in high school were of Lizzy. She was a pixie of a girl and cute as a bug. She was a sophomore when I was a senior and she was also a gymnast. She had light brown hair and probably wasn't even 5 ft tall. Gymnastics wasn't a school sport but I saw her compete when I went to see one of my buddies sister Gail who performed at a local meet. The next week at school I complimented Lizzy on her performance and we soon became friends. She was always practicing as was I. She would arrive at school in the mornings in a car driven by Gail. Gail was a senior and they practiced together before and after school. I ran in to them at a party and that's when I wanted to make Lizzy my girl. It was hard separating the two of them but I finally got her alone and got a date with Lizzy. She was so much fun to be with and after a couple of weeks I had even got to 2nd base with her. You know making out in the back seat and feeling up her titties but that was it and I ached to fuck her. She told me she was a virgin and she didn't want to lose it in a car. One week she told me that she was going to have the house to herself and told me she wanted me to come over Sat. night. She told me it would be special. My cock ached all week but I restrained from appeasing myself and save my testosterone filled load for the week end.

Saturday night finally came and I arrived at 8 o clock sharp. Lizzy opened the door and when I entered the living room the first thing I saw was Gail sitting on the sofa with a beer in her hand. WTF! What the hell was she doing there? We said hello and she got up and went to get me a beer. As soon as she left, I asked Lizzy why she was here. That's when she told me that Gail and her were lovers. It seemed that during the year they had started a little tryst together but she then told me how much she wanted to be with me that night. They had used the 'I'm staying at Gail's and vice versa to be able to have the place by themselves. And plus she told me how Gail was going to help her to please me being it was her first time with a man and if I had a problem with that. Help??? I just stammered, "That would be....uh nice." We all had a few beers and Gail told me how she had popped Lizzy cherry a couple of weeks ago so that she might enjoy her first cock a little more. I was worried about that as some of the guys had told me busting virgins wasn't great sex the first time. Now Gail wasn't exactly my type but she wasn't bad looking either. She was about Lizzy's height but with a more developed womanly body. Things were actually looking up. The girls had been drinking for a while before I got there and soon they started playing on the couch. I had to admit it was very exciting watching them in their lesbian mode. Gail took Lizzy's hand and off to the bedroom we went. The girls stripped off their clothes and jumped into bed. As they entwine it was a sharp contrast between Gail's womanly torso and Lizzy's adolescent frame. A quick glance at the night stand displayed some lube, several condoms, a 6 inch vibrator and a long double ended dong. The dong was long but it didn't have the girth my cock did. If that's what she used to deflower Lizzy they were both in for a big surprise. From the looks of things on the night stand I surmised that they must have been planning this for awhile or they were both girl scouts. My attentions quickly turned back to the girls and my package was growing by the second. I had to adjust it as it was bursting at the seams. They both rolled all over the bed as they made out and touched each other, it was so erotic. When they were close to the point of no return, Gail stopped at that time and must have noticed my huge bulge and asked me to join them. These two naked beauties were just waiting on the bed for me and I scrambled to remove my belt. My cock was rock hard and when my pants hit the floor Gail said, "Holy shit!" Lizzy also commented as to how big it was. Gail quickly told her what a lucky girl she was to have a boyfriend with such a wonderful nice cock. She had me lay down on the bed and told Lizzy to watch how she did this. She grabbed my cock and began to flick her tongue all over my shaft. She stayed away from the head of my dick and licked every where but there. This girl sure
knew how to suck dick and soon she told Lizzy to join her. She had Lizzy replace her hand on the base of my shaft and told her firmly but gently to stroke her hand up and down. They both took opposite side of my cock and Lizzy mimicked the licking Gail was preforming. Gail told her to stay away from the head of my dick for now as it was the most sensitive. It was super hot watching this two naked beauties servicing my unit. Gail said to Lizzy, "All boys love having their cocks sucked. The head is the most enjoyable for them but we don't want him cumming too soon." I could tell this slut had preformed this act many times before. Gail began to swirl her tongue over the head of my cock and I moaned out loud. "See, I told you," she exclaimed. She had Lizzy try it and soon both were darting their tongues against my bulbous head. There tongues touch occasionally and they would french kiss each other for short periods right over the top of my cock. It was much better than looking at Playboys. Gail had her watch as she engulfed about half of my rod down her throat. She preformed a nice slow head bob up and down the shaft. When she stopped she instructed Lizzy to do the same but told her to watch out for her teeth. I watched with lustful anticipation as my girlfriend wrapped her lips around the first cock she would ever suck. She was barely able to get hear small mouth around the head and a few inches but she kept her tongue going against the shaft and I was in heaven. Watching her heads alternate bobbing on top of my cock drew some more moans from my lips. "Good girl, he likes it." Gail stated. Lizzy tried to suck more and increased her pace but Gail told her slow and easy. They continued taking turns and then french kissing each other for short breaks and it was driving me wild. Gail wanted to show her one more thing and she removed Lizzy's hand and she squeezed the base of my shaft and worked her hand up it. That brought a nice sized bead of fluid out of my dick and she told Lizzy to taste it. Lizzy stuck out her tongue and licked the drop off of the tip of my dick. "It's salty." she quipped. Gail told her that was male precum and that the more excited I was the more I would produce. She also said it was time for them to stop. I didn't want that but Gail had been doing a bang up job to this point so I didn't protest. She then had Lizzy lay on her back and spread her legs. She had me come down there and it was my turn to learn. Gail's cunt was trimmed with a slender line of hair right above her slit but Lizzy was completely shaven. Gail told me that she had shaved her especially close for this night. I was thinking Gail was going to become my new best friend. I watched her closely as I had never gone down on a girl before. Usually I just stuck my cock into their mouth or their cunt and let it do all the work. Gail's tongue flicked and darted in and around Lizzy's pussy but when ever she licked her clit that drew the greatest response. Lizzy was already moaning loudly when Gail had me take a turn. Lizzy's pussy was slick with her juices and her taste was pleasant. I soon found myself enjoying it very much. "Eating a girl out before you fuck them should help them handle the huge cock you have." she said. Gail gave instructions the whole time and finally had me concentrating on Lizzy's clit. It was like eating pussy 101. Lizzy was going wild and I wanted to be the one to make her cum for the first time tonight. Gail told me, "Stick your tongue deep into her pussy and used her own juices to coat up her clit." She was right, Lizzy pussy was filled with her natural lubricate and it made her clit slippery and wet. Her pussy became slicker and slicker as her juices flowed freely. I sucked and licked there until finally Lizzy screamed and came, "Aaarrghhh!" I held my mouth hard against her cunt as she flailed about on the mattress. She eventually collapsed into a near coma and Gail told me to let her be. "Now I want you to fuck me," she stated. She told me she was on the pill and that she loved the way a man's ridges on the head of his cock felt so she didn't want me to put on a rubber. Now she spread her legs apart and pulled me down on top of her. "Eat me first and get me close," she ordered. I went down on her and she was just as sweet as Lizzy. She was close in no time. She told me she wanted me to finish her with my big dick but for me not to cum at this time. That's why she wanted me to get her close, this girl was wise beyond her years. I drove her ass into the mattress with my first stroke. "Uuugghhhh!" she yelped. Her pussy was tight befitting her frame and I shove my cock deeply into her wet cunt. I quickly brought my pumping up to full bore and she kept yelling faster and harder. She exploded on the end of my cock in under a minute, "Yessssss!" Gail ground her pussy as best as she could against me and came really hard. This girl ate pussy, sucked cock and really enjoyed getting fucked too. She was going to make some guy really happy. When she finished I pulled my cock out immediately as the temptation of cumming inside her was more than I could bear. She was still panting when I heard her tell Lizzy, "You are going love him fucking you with that beautiful cock of his." She asked us to give her a second and I moved over to Lizzy and started making out with her. We soon were in our own world and I knew that we both cared for each other deeply. The next thing I heard was Gail telling Lizzy it was time. Lizzy's eyes got really wide and she said, "It's so big." She may have been having second thoughts but Gail assured her she would be able to handle it. She had me lay on my back and told Lizzy to get on top of me. She explained that in this position she could control how much she wanted inside of her. I reached for a condom and Gail grabbed me hand to stop me. "Can you pull out just before you cum?" she asked. I swallowed and nodded yes. "Good because I want her first time to be the complete experience with your wonderful ridges pulsing inside her." she continued. This was going to be so sweet. Lizzy had to lean way forward to enable my cock to be positioned at the entrance to her virgin pussy. I felt Gail hold it up and rub the head of it up and down her slit until she stopped a ground zero. "Now just sit back at your own pace." she said. Lizzy started pressing her ass back and I felt her tight cunt enveloping the head of my cock. I saw her face winch up as she tried to get it inside her. "It's too big!" she cried. Gail told her to back up and slowly try again and that's exactly what she did. She rocked her backside slowly to and fro and more and more of my cock entered her. "It's splitting me apart." she yelled. As much as I wanted to shove my dick into her I just laid still and let Lizzy do all the work. "You're doing fine, just take your time." Gail encouraged. It was really tight but soon Lizzy had gotten about half of it inside and was gently rocking back and forth. "Hmmm." she cooed. I saw Gail look around her and wink at me as Lizzy was growing more and more accustomed to the girth of my cock. Lizzy's eyes were squeezed shut and she said, "Is it almost all in." Gail told her almost which was a bit of a reach. It felt great and it was a good thing that we ate her out first. Lizzy started groaning some as she took more of my offering. "It still feels like a lot of pressure." she moaned. That's when Gail told her to turn around and face the other way. Lizzy lifted her cunt off my cock and turn around to ride me reverse cowboy. This time she held it herself as she lowered her pussy onto it. Once again she could only get a little more than half of it into her. Gail told her to lay back and she placed her arms by my shoulders. We stayed completely still but she began to moan softly. I couldn't see much but from the sounds I could tell Gail was munching on her cunt. Damn, this girl could make a living out of this. She was sucking Lizzy clit and settled her down at the same time. Soon Gail told me to start fucking her very slowly. Lizzy accepted my strokes and soon I had about 3/4 of my dick inside her. Gail's mouth had Lizzy's cunt juices flowing and my cock were reaching new depths every second. While I wasn't balls deep her pussy was still exceptional warm and tight and I yearned to let loose a salvo. Thankfully Lizzy got there first. She ground her cunt down on my cock jackhammer fashion and she began to wail, "Fuck me, fuck me, fuck meeeeee!" I could feel the walls of her pussy spasming around my shaft and her cervix pressing against the head of my cock. And she achieved her first male cock orgasm. When she finished she fell back on my chest and I mauled her small titties as I continued to shove my cock into her. Gail asked me if I was close and I told her I was. She told my recovering girlfriend that she would have to roll off soon. My cock began to throb and I yelled, "Now." I push Lizzy over to the side as Gail pulled my dick out of her cunt at the same time. Gail latched her mouth onto it and started suction sucking my cock. "Uugghh!" I grunted and I thought my first shot could have come out through the top of her head. I was rocketing cum into Gail's mouth and that little slut didn't miss a drop. I think she was surprised by the volume of my load as she garbled, "Oh my!" Lizzy moved closer to watch and that's when Gail came up for air and said, "Help me." Before Lizzy could take over one stream slipped out and cascade straight up and back down on the head of my cock. It looked like a glazed dough nut. Lizzy's mouth covered my cock after that and it was her turn to drink from my fountain. She gagged a little once and swallowed like a trooper. My cock wound down and she took her mouth off of it. They both stared at each other not quite believing anyone could cum that much. I felt Gail work her hand up my shaft once more and a good sized blob of male semen came out on the tip of my dick. She extended her tongue out and licked it up. She kept the cum covered tip of her tongue out and moved toward Lizzy. Lizzy extended her tongue in kind and they met above my receding dick. They swapped cum covered tongues before sticking them into the others respective throats. They made out passionately for a bit before Lizzy broke off and said, "It's not as sweet as we are." Gail laughed and stuck her middle finger deep inside of her cunt. Then she pushed it into Lizzy's mouth and she sucked on it greedily.They embraced and were off to the races again. I was spent and didn't think I could go again but after watching this lesbian display my cock started to show signs of life. And when the two of them started eating each other out in a 69 position, my cock started throbbing and I wanted to fuck some more. I ended up fucking whoever's pussy was on top. The evening ended with me filling Gail's cunt full of man juice and she loved it. That was the first time my dick was actually raw after wards. Although I was dating Lizzy, the three of us got together lots of times that year. It ended at the end of the summer with Gail and I going off to college. We all drifted apart with the long distance relationship and I'm sure Gail was schooling freshman at her new college. Lizzy would always have a special place in my heart and Gail a special place on my cock.

End of Story