School had just let out for the summer and Megan and I were still together. I knew it would be only a few more months before school would start up again and we’d have our first anniversary as a couple. I was looking forward to it, hoping that she was getting comfortable enough with me being her steady and serious boyfriend that we might do more than just kissing and touching above our clothes.
I was ready and willing, but being a twenty-year-old man meant I was ready to fuck at the drop of a hat, or skirt as the case may have been. True we both promised to remain virgins until we were married, but lately she seemed to be loosening that, hinting more that she wanted to make sure she only lost her virginity to Mr. Right, whom she would of course marry. That gave me some hopes some before we graduated and were married, so I stoically resisted temptation to push her and contented myself with porn magazines and my right hand.
Well, mostly. Sure, I’d lost my virginity to her then sixteen-year-old younger sister Abby, and taken her virginity, and even got her pregnant doing it to boot. She’d covered for me and kept our secret by saying she’d been date-raped while drunk at a party and didn’t know who the father was, but that she was keeping it anyway. I was conflicted about that, and thought about asking her about abortion, but the thought of killing my baby and having no ‘official’ reason to broach the subject kept me silent.
Then of course there was her mother, Alice, who had decided that her daughter was going to enjoy her first time and she had to make sure I knew all about the ins and outs of sex. So with a twenty-four hour long day and night home class she gave me on the subject, she taught me how to really make love to a woman, and how to fuck like a man. It was a ball-draining experience that I still daydream about, and occasionally jerk off to today.
Now I’d not had any sex for a few months, and still claimed to the world, and more importantly Megan, that I was a virgin, despite my two indiscretions. And since neither of them and any intention of ever telling another living soul, I was happily still with Megan. The month of summer since school ended saw us dating every weekend while we both worked summer jobs to make some money. I wondered when I should do the official proposal to her, and about how much rings cost, but decided that with still three years of school there would be plenty of time for that later.
I had made up a lot of excuses to keep from hanging out at Megan’s house, mostly to avoid spending possibly uncomfortable time with Abby and Alice. Alice was fine and acted like a normal mother as ever, but Abby, now six months pregnant with my child and still crushing on me, was a disaster waiting to happen with the amount of hormones between us. So I made sure I was with Megan all the time around either one of them. This was mostly because I didn’t trust myself not to engage in carnal pleasures with them again if given the chance.
Megan called one Friday and said, “We are going to a party.” Interested to do anything with her out of her house I agreed and she continued to tell me the details. “It’s at my friend Brooke’s house. There’s only going to be a few people. Mostly just Judy and a few guys they like.” We agreed and that night I picked her up outside her door and we drove down the couple of blocks to Brooke’s house.
Megan told me Brooke was a childhood friend of hers and while they had gone to different colleges, they tried to keep in touch. Judy actually went to our local college also, but I’d just never met her since she was more Brooke’s friend than Megan’s and was a year older than us so she was in totally different classes. Megan didn’t know the guys, but I wasn’t worried about my girlfriend straying from me. “Alcohol?,” I asked. Neither Megan nor I drank much. I just didn’t like the taste, while she didn’t want to lose any brain cells to keep getting the best grades she could.
“I don’t think there will be any, but I didn’t ask,” Megan said. That was good enough for me.
We arrived and found it was just the six of us. I was introduced to Brooke and the guy she was looking at dating, Rod. Brooke was a little larger than Megan, but shorter. She wasn’t actually fat, just with a little wider build and more curvaceous with a big round ass. She also had short curly black hair and big pouty lips. Overall she was quite attractive. Rod was a normal guy; he was into computers and taking engineering classes as Brooke’s college.
Then I was introduced to Judy and her date Steve. Judy was very tall and had shoulder length straight brown hair. She was thin as a bean-pole and had no tits or ass to speak of. Steve was just introduced as her friend and was kind of quiet and didn’t talk much.
It seems Rod had brought a bottle of Jack Daniels and wanted to start the night off with everyone doing some shots. Brooke was all excited for that so Megan and I went along to indulge our hostess. I mean, we were fine and not driving again for several hours.
We played some cards and talked, and eventually Judy was recalling good times she’d had with the other girls and said, “Remember that one party and we played Truth or Dare?”
Megan blushed and fidgeted like she does when she’s embarrassed. Now I was curious. “What happened?”
Megan, “Nothing… It was just a game and we were kids.”
Brooke interrupted her, “Nothing?” She laughed, “That was only when Megan got her first kiss.” Megan turned beat red, but that seemed to inspire Brooke, “We should totally play that!”
Megan stammered, “What? No way.”
Then I saw my opening, “Come on Sweetie. I’m here. What’s the worst that could happen?”
She hemmed and hawed, but eventually gave in and we all sat in a circle on the floor with an old bottle that Brooke said had been her first liquor bottle. Around the circle from me were Megan to my left, then Judy, Brooke, Rob, and finally Steve to my other side completing the circle. She started off spinning it and it pointed at Rod who said quickly, “Truth.”
Brooke continued, “If you could sleep with any girl here, who would it be?”
“Wow, right to the jugular Brooke,” I chastised her.
“It’s OK,” Rod said. “I would sleep with you Brooke,” he said with a smile. Then turning to look at the other girls he added, “But I would fuck any of you fine hoochies.” It looked like none of the girls liked that answer, but Rod just had a smug look on his face as he spun and got Steve, “Truth or Dare Steve?”
“I’ll take the dare,” he quickly decided.
Rod smiled and said with a devious smile, “I dare you to kiss Megan full on the mouth, for 30 seconds.”
“No,” Megan said.
“Then you have to drink,” said Brooke cheerfully and poured Megan another shot. Megan scowled at her and downed it. “And one for Steve…” Brooke said pouring his glass.
“But I didn’t refuse the dare?” he complained.
“Did you do it?” Brooke asked all mater-of-factly and he just shut up and drank.
Then Steve spun and got Megan who said, “Truth,” flatly and unimpressed with the game.
“Where was the first time you ever had sex?” Steve asked.
“You wasted your turn,” I laughed.
“She has to answer truthfully,” Steve protested.
“I’m a virgin Steve,” Megan stated proudly. “Unlike some of the other people…”
I didn’t make eye contact with her to hide my guilty conscience, but she quickly spun and got Brooke. “Brooke, truth or dare?”
“Truth, I guess,” she said.
“Hmmm, well then I’m giving it right back at you for wanting to play this stupid game,” Megan said. “If you could fuck anyone here, man or woman, who would it be?”
Brooke looked at Rod, but his earlier comments seemed to have turned her off to him now. She didn’t really know Steve or me, so pondered a bit before she replied. “Megan’s boyfriend Adam is kind of hot. I’d probably fuck him in a heartbeat if he was available. But Megan would never let me. So there.”
Megan looked proud to have the stud of the room, and thus be the top girl by association. I took it as a complement and Brooke spun the bottle and it pointed to me for the first time. “I’ll take the dare,” I replied. “I’m not a wimp.” I felt that now being the stud that I had to keep up the image.
Just then Megan leaned over and whispered something to Brooke. “You sure?” Brooke asked, and Megan just nodded. “Adam, you have to make out with me.”
I looked puzzled at my girlfriend who just offered me up to her best friend who had just said she’d fuck me if given the chance. She just smiled and I sighed, “Ok…” as I leaned over and kissed her quickly on those big pouty lips.
“That’s not making out,” Judy protested. So I leaned back in to a smiling Brooke and was more vigorous. I’d had plenty of practice kissing Megan, as that’s all we ever really did so far. But both her sister Abby and mother Alice are better kissers and I’d learned quite a lot. I don’t think Brooke ever learned to kiss as she was a little slobbery and clumsy, but I made sure she enjoyed it for about a minute before we parted.
“Wow,” Brooke said with a sigh. “Your boyfriend is a terrific kisser.” Again she was proud and I was honored and a little turned on to be the center of attention.
The bottle spun and funny truths were told and other couples kissed, including me and Judy, Judy and Steve, and even Judy and Brooke to loud cat-calls from all. Rod kept trying to get Judy to kiss him, but whenever he got her she always said truth. Instead he got some of his sexual frustration out by trying to make Brooke or Megan do sexual things. Usually they just took the shot and retaliated against him by trying to make him do stupid and embarrassing things that forced him to take more shots.
After what must have been an hour we’d all had a number of shots and had lost a few articles of clothes. I somehow was out of my jeans, and Brooke was topless but for her bra. Steve had gone to the bathroom in one dare and was wearing his underwear on his head. Judy was actually the most naked wearing only in her very small A-cup bra and panties. Both Rod and Megan were still fully dressed, but both had drunken far more alcohol for it.
The bottle was running low and I was definitely feeling its effects when Rod spun the bottle to me. “Dare, I said.”
“Yous got to jerk off on Brooke’s tittiesh,” he said with a clear drunken slur.
I was about to refuse and down my drink when Megan beat me to it, “No way! Heish mine boyfriend!”
Rod cut in before we drank and compromised, “Wait, instead… You have to let Brooke rub your cock through your pants.”
I looked at Megan and she didn’t look so cogent, but thought for a second then nodded saying, “Ya, shur, OK.”
Brooke didn’t waste any time once she’d gotten permission. She knelt in front of me and grabbed eagerly for my junk. I think she was disappointed I wasn’t erect, but there were a lot of people around, so my nervousness had kept me soft short of such direct contact. But now that a busty woman was rubbing me I quickly began to grow. Nervous that I’d be poking up in front of everyone now I said, “Ok, there. She did it,” and pulled back from her. Brooke didn’t argue, but was a little depressed at having to stop.
Steve and I tried to keep to more friendly and funny topics, but Rod and Brooke were both just pushing lusty questions and dares now.
Judy finally had another drink instead of removing her top and decided it was time to go. Steve was her ride and he was still sober enough to drive her home after they put on their missing clothes. A few more spins and drinks later and Megan passed out. Brooke had me carry her to Brooke’s bed to let her sleep it off for a bit, but Rob and Brooke wanted to keep playing so I obliged.
Megan spun Rob who choose with a slutty voice, “Dare.”
She smiled at him like a snake and said, “You need to make out with Adam.”
I laughed and made a pucker up face to joke with him, but he just took his shot in anger at being made fun of. Then his eyes bulged, and he got up and wobbly ran to the bathroom. We laughed as he puked for a few minutes, then he huffed, got his stuff and left.
“God, I thought he would never leave,” Brooke said thankfully.
“I thought he was your date?” I asked.
“I thought he was cute in class, but I didn’t know him at all,” she confessed. “You heard him trying to hit on Judy and Megan all night.” She shrugged and frowned, “He only hit on me once they were gone. No one wants a fatty like me.”
“That’s not true,” I tried to defend her honor, “You’re a cute girl and I’d totally date you if I weren’t already spoken for.”
She blushed and smiled at me, “Really? You’re just saying that.”
“No really,” I said honestly. “I’d have totally dated you if I’d met you before Megan.”
Then Brooke grabbed the bottle and pointed it at me, “Prove it.”
We both laughed and were more than a little drunk, but when those big pouty lips touched mine I lost control of reason and awareness. I’d had blue balls for more than two months and my little brain was overruling my big drunken brain and we hurriedly started undressing each other the rest of the way. I got her bra off while she pulled down my briefs. My hands pawed at those huge tits and she started jacking my cock to full mast. Then her head dipped down and she started licking and sucking on my manhood. It wasn’t the best blowjob I’d ever gotten, but beggars cannot be choosers and it felt great to have a girls lips around my cock again instead of my hand.
I kept squeezing her big floppy tits and thrust up a bit and caught her by surprise and she gagged a bit. She pulled off and caught her breath and I unbuttoned her jeans and pulled then roughly off her large hips and ass. I was pleasantly surprised to see she wasn’t wearing panties and I stood up with her, kissing her again, and she pulled me with her to the couch.
“Please fuck me Adam,” she begged me as she sat on the couch and spread her thick legs and showed me her black tangled hairy pussy. “Megan will never know.”
Megan? Fuck! She was asleep just a few rooms away. “Brooke, we can’t,” I began to argue. “I love Megan, and you are her best friend.”
“Can you honestly tell me you don’t want to fuck?” she asked sitting up. I was silent as the night’s events raced back through my head. She took my silence as acceptance and pulled my shirt to bring me to her.
“Brooke we can’t, please. I won’t cheat on Megan. I won’t.” But she put her lips back around my cock and ended my feeble resistance. She definitely wasn’t as experienced as Alice had been, but this wasn’t her first time sucking a cock either. I was beginning to throb and my head was getting dizzy when her moist lips released me again and she pulled me down by my shirt and between her splayed thighs.
“It’s my first time too Adam,” she confessed, thinking I was a virgin as well. “I’ve got a dildo, so don’t have my hymen anymore, so please just do me.”
“Oh God I want you so bad,” I blurted out as I knelt down. We had nothing between us, nothing to stop me from entering her. My shaft was hard and ready. I rubbed it up and down her wet slit, realizing she really was ready too and I pressed my dick into her warm pussy.
I looked at her and she just nodded and bit her lip. I pushed in further and Brooke gasped, but she was so warm, so wet, so ready for me that I began fucking her in earnest, not too fast though, just a slow and steady thrusting. I didn’t want this to end too soon as I really needed a good cum. She had more padding from her extra pounds, but it made it rather nice and soft as I just let all my weight fall on her as I rocked my hips letting my cock slide in and out of her love canal.
I knew I was going to cum before her if I kept this up, so I remembered what Alice had said. I pulled out and sat next to her on the couch. She didn’t need prompting and quickly straddled my hips as I held my cock up to let her spear herself down onto me. But this time there was no stroking in and out. She just sat on top of me with my prick deep in her cunt. Then I felt it, the squeezing and release. Her pussy was wrapped around my shaft and she was gripping me hard with her muscles and then relaxing, over and over. I had never felt anything like it from Abby or Alice. It was so different, so wonderful. I felt my climax approaching, brought on by this girls cunt muscles alone.
“Brooke, you’re going to make me cum,” I announced.
“That’s the idea, baby,” she replied without stopping her squeezing. It wasn’t a minute more and her powerful pussy muscles were sucking up every ounce of my cum. “That’s the way. Give momma all your cum.”
Whatever she was saying I had to obey. I couldn’t have stopped cuming for Brooke right then if my life depended on it. But something different was happening. After I had given every drop I could, she continued the squeezing and relaxing and I didn’t go limp.
“Oh Brooke, I’m still hard,” I told her.
“Didn’t Megan tell you I’m majoring in gynecology? I’ve spent the last two years practicing my Kegel exercises and I’ve wanted to try them out a guy for some time,” she bragged as she began to rock her hips forwards and backwards, fucking me now while still clamping her muscles on my cock rhythmically. I rocked my hips with her as best I could, but mostly just grabbed her hips and enjoyed the ride. “You’re going to get the fuck of a lifetime.” She was right and it felt so damn wonderful I couldn’t argue.
I could tell she was starting to get close, but after a few minutes she stood up saying, “I want you to take me from behind,” as she knelt next to me on the couch with her hands on the back and her big round ass sticking up with her wet gash staring at me. I stood up and got behind her and quickly guided my dick back into her sopping wet cunt. I took a hold of her wide hips, and began pounding into her hard. She had plenty of meat and her ass and it giggled as I rammed into her as hard as I could.
“Oh fuck Adam that feels so good,” she exclaimed. “Don’t stop baby, don’t stop. Fuck me harder!”
I didn’t see how I could go much harder but I tried. I began jack hammering her as fast as I could until I heard her cry out, “Oh shit! I’m cuming so hard.”
This was one of the most incredible fucks of my life and as she screamed into the couch cushion I pushed one last time and held myself deep inside of Brooke’s spasming vagina as I began shotgunning my cum into her formerly virginal womb. I never thought I would cheat on Brooke again, let alone that I would be enjoying it so much. Then for the briefest of moments I couldn’t imagine myself fucking anyone else. For that short period of time, Brooke was all I ever could want, all I ever would want. I pulled out and fell onto the couch. Brooke collapsed down next to me, kissing my shoulder as she came back to earth.
It seemed like an eternity before either of us spoke, but finally I did. “Brooke.”
But she interrupted me. “Listen Adam, I know you are with Megan. But I also know she will be a virgin for a long time yet. I just want you to know that I am here for you whenever you want, you know, to take care of you when you need it, when you want it, like tonight.”
“Wow,” was all I could get out.
“Did you enjoy yourself?” she asked.
“When people look at you Brooke, most can’t get past your, uh, size,” I stammered. “How little they know. I think that’s the best fuck I have, I mean, I will ever have. You’ll need to teach Megan those Kegel things.” She laughed and we just sat there naked in the afterglow in each other’s arms for a while.