Author’s note: Right now this is definitely going to be at least a two-parter.
My name is Joe. This story is about my best friend Rich getting lucky with his mom and older sister during the summer after we graduated high school and how I was fortunate enough to join in.
Since his parents’ divorce, Rich lived with his older sister Sherry and his mom. During the fall of our senior year, Rich and I turned 18 and hit the weight room to get in better shape and it paid off as we both packed on extra muscle and it showed. In our senior year of high school, after we turned 18, we would jokingly call Rich “Big Man Dick” because while showering after gym class we noticed he has a huge cock.
At graduation, Rich told me he couldn’t believe how great Sherry looked. He said during her year away at college instead of putting on the freshman 15, she lost weight and let her hair grow down past her shoulders. He also told me that while he was getting dressed for graduation she was back to her old tormenting ways. During our junior year, when she was a senior, she’d torture Rich about how scrawny he was. During her semester break (after we turned 18) she heard porn coming from his room and started giving him a hard time about cleaning up. Now, before graduation, she knocked on his door asking if he was starting the festivities with a bang and needed to clean-up.
“We’ll find a way to get her,” I assured him at graduation.
After graduation we did the usual thing and went party-hopping for a few hours, but we couldn’t find one we wanted to stay at. We wound up going back to Rich’s house for a swim in his pool and to steal a few beers from the fridge.
We were hanging out poolside, sitting up in lounge chairs, when Sherry came out wearing a lacy red sheer cover-up robe. It was evident she was nude underneath, probably intending to go skinny-dipping. Sherry’s 5-foot-8, green eyes, strawberry blonde hair, curves in all the right places, and 40-D breasts.
“Oh my god!” she yelled when she saw us. “What the hell are you two doing here? Shouldn’t you be out partying, getting drunk?”
“We couldn’t find any parties we liked,” I said. “Besides we figured having a beer and swimming was better. Also, I have to say that you look great, especially with the longer hair. The year away has treated you well.”
“You really think I look great?” she asked, a little surprised.
“Yes we do,” I replied motioning at Rich who nodded in agreement.
I started to rub my hardening cock through my bathing suit and I noticed Rich was doing the same.
“I didn’t think I’d do this in front of either of you,” she said. “But for a graduation gift, what the hell, happy graduation.”
She smiled as she dropped the robe exposing her naked body.
I eased my suit down, exposing my 7-inch cock, continuing to stroke with a slow steady rhythm while staring lustfully at her, trying to let her know I wanted her. Rich had lowered his swim suit and was stroking his big 11-inch a little faster.
She looked at both of us with a big grin and turned to her brother first.
“Richie, slow down, we don’t want any clean-ups yet,” she laughed. “Just sit back and enjoy the show.”
Then she turned to me.
“Joe, look good enough to eat,” she said as she walked over licking her lips.
She knelt next to me, grabbed my cock in her hand and lowered her mouth over it.
Her lips felt exquisite as they slid up and down my cock. Her tongue teased me while it was in her mouth. She bobbed her head up and down several times, sucking with just the right touch, before removing me from her mouth and running her tongue up and down the length.
I had one girlfriend try giving me a blowjob earlier in the year, but it was nothing like this. I was in heaven. She started stroking my shaft while taking my balls into her mouth one at a time and then running her tongue over them.
She then climbed onto the lounger, straddling me, rubbing her tits against my chest before leaning in and giving me a kiss. Our lips parted and our tongues danced before she whispered in my ear.
“If we had some condoms out here I’d be riding you until you shot hard, but since we don’t you’ll have to settle for this.”
With that she slid back down my body, wrapped her magnificent breasts around my cock and started rubbing them up and down, giving me a tit fuck.
“Cum for me, give me something to clean up,” she cooed.
She stared rubbing them faster and repeated her plea.
“Move your mouth back to my cock,” I moaned.
She did and started bobbing up and down on it wildly with just the right amount of pressure and suction between her lips.
“That’s it, I’m cumming” I groaned and started to shoot.
She took the first two shots in her mouth before taking me out of her mouth and aiming the rest on her breasts and in her cleavage.
“Fantastic,” she smiled at me and got up.
She lifted her breast to her mouth and licked some off. Then she swiped a finger over the cum, scooping it up and then licking sakarya escort it off her finger. She did this several times before smiling at me.
“Delicious,” she said.
Then she turned to Rich, with some cum still on them.
“Your turn baby bro,” she said as she walked over to him and got on her knees again. “I’ve been wanting to do this since I saw how big you were last year when you caught me in the shower. But I knew I had to wait until after graduation.”
She started to slowly bob up mouth up and down on his shaft but was having trouble getting all of it in her mouth.
“My god, you’re huge,” she said. “We’ll have to change positions for me to deep throat you, taking it all in, come sit on the table.”
Rich quickly got up and sat on the edge of one of the tables while Sherry bent over in front of him and went back to work. In this position she was able to go down nearly to the base of his cock, leaving less than an inch, and he was moaning in pleasure.
Also in this position, bent over at the waist, her pussy was on full display and pointing at me.
She shifted from sucking on him to licking and stroking the entire length of his shaft. They were both moaning contentedly and I was stroking myself getting hard at the sight of this.
She started sucking his balls while continuing to stroke him with both hands, causing him to moan louder and put his hands in her hair.
Moments later she started to tit fuck him and I was as hard as a rock.
“We can’t have any more messes to cleanup,” she laughed before taking him back into her mouth.
At this point I couldn’t take it anymore and got up and stood behind her.
“I’m sorry, but I’ve got to do this and I promise to pull out,” I said before grabbing her hips and pushing my cock into her.
“Shit, that feels so good,” she moaned after taking her mouth off his cock for a minute.
She was using her pussy muscles to squeeze my cock tightly as she bucks her hips back to meet my thrusts.
“Oh god, I’m gonna cum,” Rich moaned as her grabbed her hair, holding her head in place.
“Oh shit,” I said as I quickly tried pulling out, not quite in time, as my first blast was partially in her and the second coated her pussy lips as I pulled out. I kept cumming and streams of it landed all over her back and ass.
“You were delicious too,” she smiled at Rich, sticking her cum covered tongue out at him before wiping her mouth.
It was at this moment that the door from the house to the pool opened.
“Oh my God! What the hell is going on here?!” their mom shrieked at seeing me with my semi-hard cock standing behind her daughter, her back and ass covered in cum, and her son’s large still semi-hard cock covered in saliva and cum in front of her daughter.
“Joe, get on your suit and go home now! The two of you go to your rooms and I’ll speak to each of you privately,” their mom said.
“Sorry Mrs. R,” I said as I quickly moved back to my bathing suit to put it back on. “We were celebrating graduation and things got a little carried away.”
“I’ll say so,” she replied while staring at my cock. “It will take me some time to get over this! You two to your rooms!”
While putting her robe back, Sherry looked at me, smiled, held her hand up to her ear and mouthed “Call me”
I didn’t have Sherry’s cell number and I waited an hour before calling Rich to see how bad things were. He didn’t answer his phone.
Late the next morning, he called me and told me the unbelievable tale of what happened after I left.
While he was in his room, cleaning up he had started to masturbate thinking about fucking Sherry when his mom knocked at the door and came right in before he could cover himself. While staring at his cock she stammered about how it was morally wrong to be engaged in sexual activity with a relative and she didn’t want it happening again. She said she told Sherry the same thing and was sending Sherry in to apologize for taking advantage of him.
Sherry knocked on his door and laughed asking if there was any cleanup needed yet.
After he told her no, she said good and barged in.
She saw him lying in bed with his hard-on in hand and told him to stop.
He told me that Sherry said that she was supposed to apologize but couldn’t resist and put a condom on him that she brought in with her.
She climbed on and started riding him, slowly at first, but then building up speed, her tits swinging freely and she was moaning loudly how good it felt.
Their mom barged in and shouted what the hell was going on.
He says that Sherry spoke up and apologized to their mom saying how good Rich’s cock felt and then told their mom to get naked and straddle his face.
Both he and his mom were shocked at the demand.
He went on to say that Sherry asked their mom something about would she rather he learn about sex from them or from watching porn. Sherry then offered to keep him hard if their mom taught him pussy eating and had escort sakarya him get her nice and wet.
He claims his Mom said Sherry was right and got naked. She straddled his face and for the next 15 minutes instructed him on how to eat pussy. At this point between mom’s moans and Sherry’s moans he said he couldn’t take it anymore and came hard.
The tale continued as his Mom asked Sherry to get him ready for her and Sherry gave him an amazing blowjob. Once he was rock hard, Mom it was her turn and dragged him off by the cock to her bed. He said that Sherry laughed and called her a hypocrite.
He said his mom started off saying she wanted to teach him about every way to have sex. She got on her back and after getting a new condom on him, instructed him to get between her legs and how to enter her. They had gone at it just a few strokes before she told him to stop, she couldn’t stand looking at his face while they fucked. She had him pull out. She had him fuck her from behind while she was on her knees, while she was bent over standing up and she also spent some time riding him with her back to him. They fucked for two hours and he came twice. He said after cumming the first time, his mom gave him a handjob and whispered to him she was amazed at how big and how good he felt and that she wanted him to get hard again.
I have to admit I was getting hard listening to this and picturing it in my mind as his mom is hot and I would fuck her if given the chance. With light brown shoulder-length hair, green eyes, a nice figure, and what must’ve been D-cup breasts, who wouldn’t want to bang her?
But he wasn’t done with the story yet. He said he returned to his room to rest, but a few minutes later Sherry came in, saying she heard what was going on and wanted to fuck him missionary. She got on her back and raised her legs. He entered her slowly without putting a condom on. As he gradually built up speed Sherry wrapped her legs around him and they moved like a well- oiled machine until he pulled out and shot all over belly. He said he joked with her “clean up needed on aisle belly”. She flipped him the bird and grabbed one of his t-shirts to clean herself off. He rolled her over onto her stomach and moved to fuck her in the ass, but she stopped him, saying that was off-limits. She went back to her own room to sleep.
He said at breakfast Sherry joked with her mom they should open a “Family and Friends Fuck Lessons” business so they could both get some over the summer. Her mom laughed and said a few friends might be possible, but a widespread business was out. He said Sherry laughed and asked if Joe could be the first client as he had a nice cock. He says his mom smiled at that comment and agreed. Rich told me he said I would definitely be interested and he’d call to set things up.
“So, how soon do you think you can come over?” he asked.
“Right now,” I said. “Should I come to the front door or the pool?”
“The pool in 15 minutes,” he said.
I put on a pair of Speedos and drove over. I sat in the driveway for another five minutes watching some porn on my cellphone rubbing my cock so I would have a clear hard-on when I went back there. I went in the pool entrance and my jaw dropped at what I saw.
Everyone was naked. There was a box of condoms and some lube on the table. The three of them were sitting in chairs and were all masturbating. Rich had his head back and his eyes closed as he stroked. Sherry had her legs close together and was rubbing her pussy while staring at her brother’s cock. Their mom was leaning back slightly with her eyes closed, legs spread, her right hand rubbing her pussy and her left caressing a breast.
“Hello, I’m here!” I called out.
“Hey Joe,” Sherry said taking her eyes off her brother. “We’re having a contest to see who can cum first. You’re a little overdressed, but are welcome to join in.”
Their mom opened her eyes, looked at me and smiled as I managed to get the Speedo over my hard-on.
I started to jerk off watching all of this.
Moments later, their mom started to moan loudly and her body shook slightly as she had a spectacular orgasm.
“Sherry open wide,” I said I turned in her direction and tried getting my cock into her mouth before shooting, but some landed her breasts before I could get it into her mouth. The sight of this set Rich off.
“Why didn’t you give it to me?” their mom asked.
“Sorry Mrs. R, I didn’t know you wanted it,” I replied.
“I do want it and stop with the Mrs. R crap, call me Joanne,” she said.
“You won Mom,” Sherry said. “What are the first pairings going to be?”
“We’ll give your brother some recovery time,” Joanne said. “I’m going to straddle Joe’s face and teach him how to eat pussy while you do what you want with his cock, just make sure it’s ready for me to ride when I’m ready.”
“Sounds good to me,” Sherry said eagerly.
“What the hell am I supposed to do besides clean up?” Rich groaned.
“Sit back, enjoy the show, sakarya escort bayan and join in when you’re ready,” Joanne said.
I was laid onto my back and Joanne was a master teacher, rubbing her fingers and pointing to the spots where she wanted me lick or nibble. With Joanne’s thighs straddling my face, my tongue buried in the folds of her pussy and Sherry’s mouth and tongue working their magic on my cock I was in heaven.
I don’t know how long it was, but eventually Joanne stopped pointing and let me go on auto-pilot as she held my head in place letting out long moans of pleasure. She tasted sweet and my face was getting wetter with her juices by the minute. At the other end, Sherry had me rock hard and paused for a minute to get a condom before starting to ride me.
The sight of them double-teaming me and their moans must’ve been getting to be too much for Rich, who decided it was time to come over and join in. The ladies’ moans were getting muffled and I heard Rich speak.
“That’s it Sherry, keep sucking the shaft and mom keep sucking on my balls,” he said. “I’m getting close, who wants my load?”
“I’ll take it,” Sherry said as she stopped riding me for a minute to focus on her brother.
“Damn, you’re still hard,” Sherry said to him.
“Mom, Joe’s still hard, he’s all yours but I need Rich’s monster cock pounding me,” Sherry said. She obviously did something to keep Rich from cumming.
With that Joanne got off my face and rolled onto her back.
“Fuck me good big boy,” she said to me. “Remember to start slow and gentle, building speed gradually. Let my moans be your guide.”
I rolled over between her legs and lifted them slightly before pushing myself inside.
I followed her instructions and started with slow, short thrusts as I adjusted to her tightness.
“God, you feel so tight and so good, better than your daughter,” I said.
“Good,” she smiled up at me.
I was laying on top of Joanne, looking into her eyes before we kissed deeply. She began to moan louder so I began to increase the intensity of my thrusting.
I heard the unmistakable sound of a slap and a moan and looked up to see Sherry kneeling on a lounge chair with Rich standing behind her thrusting hard into her pussy and slapping her ass.
Joanne grabbed my face and pulled me to hers, staring into my eyes before kissing me.
“Focus on me,” she said as she started to gently gyrate her hips up against mine, pushing to meet my thrusts. “Start going faster and harder.”
It was heavenly in this position, looking into her eyes, looking down to see her breasts bouncing with each thrust, feeling her legs rubbing against me before wrapping them around me. I didn’t want this to end too quickly.
Instead of following her instructions, I continued to use short, rapid, gentle, thrusts, enjoying the moment.
“Fuck me harder and faster,” Joanne said. “That’s how you do it if you want us cumming hard together.”
With that I moved her legs onto my shoulders and started slamming into her as hard and fast as I could.
“Is this what you wanted,” I asked, staring into her eyes.
“Yes,” she panted. “The eye contact, the thrusting, the passion, it’s perfect.”
“Mmmmmm, feels so good, I’m cumming” she moaned. “Keep going, ride me to another.”
I slid her legs off my shoulders as I continued to thrust so I could lean in and suck on her bouncing tits. Then I moved up and kissed her passionately.
“Oh shit, I’m almost there,” I said.
“So am I baby, just a little bit more,” she said.
Moments later I groaned I was cumming and at the same time she let out a long satisfied moan that she was cumming too.
As we laid there sweating, catching our breath and hugging, we heard applause.
We turned to see Sherry and Rich clapping and cheering complementing us on our performance.
Then Sherry and Rich came over and helped us up to our feet. Rich had another hard-on and was spinning Joanne around.
“What’s the matter baby?” Joanne said to Rich. “Did Joe’s performance make you jealous? Do you want to try making mommy cum again?”
“Yes I do,” Rich said as he bent her over a chair and thrust into her.
“I heard what you said to her,” Sherry said to me while peeling off the condom and tugging on my cock. “I’m going to have to see if I can change your mind about who’s better.”
Sherry started giving me a blowjob to get me hard, taking me in her mouth.
“Your BJs are amazing, I can’t imagine your mom being better in the oral department than you are,” I said.
“Good,” Sherry said. “Now it’s time to prove to you my pussy is also better.”
With that she moved me to a chair, sat me down, and then got a condom and straddled my lap. She went for the direct approach — grabbing my cock, holding it straight up and lowering herself onto me quickly. Once she was fully impaled she started rocking her hips back and forth grinding, instead of riding me.
“How does that feel?” she asked, looking into my eyes.
“Great, but your mom still felt better,” I said with an evil grin.
At this point we heard a grunt and looked over to see Rich shaking in orgasm and Joanne starting to stand up telling him he didn’t give mommy multiples like Joe did. She started stroking his cock begging him to get hard again.