Rich’s Family Fun: Freshman Year

Author’s note: This is a long overdue follow-up story to Rich’s Family Fun Summer. All characters are over 18. Written messages (texts) are in italics.

My name is Joe and to recap what happened in Part One of the story. On the night my buddy “big dick” Rich and I graduated high school, his older sister Sherry gave both of us a blowjob and I got to fuck her right before their mom came home and saw what was going on. After I was sent home, Rich got to fuck Sherry and his mom (Joanne). The next day I was invited over to join in the fun. It was a summer of sex, but by mid-summer, Sherry and I were fucking each other exclusively while Rich was paired off with his mom.

When the end of August arrived, we had to go our separate ways, Rich went to college halfway across the country, but in the same city as his Aunt Stephanie, who happens to be Joanne’s twin sister. Sherry and I went to different colleges a state away, but only two hours apart from each other.

Now on with the story.

We were away at college for less than a week when I got a text from Rich.

Holy shit! My Aunt is smokin’ hot. She fucks better than mom and her blowjobs put Sherry’s to shame. You need to get out here to experience her mouth and body. The message was followed by two pictures — one of a hot woman reverse cowgirl on his cock, the other of a woman’s lips on the base of his cock, the rest of it in her mouth and down her throat.

I wrote him an angry message back

Rich! Stop fucking your relatives! A guy with your 11-inch cock and your skills can easily be scoring with any girl you want on any night. Hell you can probably get some hot girls on campus to double-team you. Starting fucking the girls our age.

Rich wrote back:

You’re kidding me? When I can have a mature woman like my Aunt with a mouth and pussy as skilled as hers, why would I go for young college kids? Just let me enjoy myself. Talk to you later.

Joanne used her new confidence and continued to gorge herself on sex with new partners. She texted a picture to Rich, Sherry, and I captioned “Wish You Were Here”. It was a picture someone took of her riding a cock, with another in her ass, and her face buried in a pussy.

Soon after that I called Sherry.

“Hey baby, how are you?” I said.

“Hungry for your cock,” she replied. “But otherwise I’m good. How are you?”

“I’m good,” I said. “But I wish my cock was buried in your pussy right now.”

“Looks like we’ll have to schedule a weekend visit,” she said. “What else is going on?”

“Have you heard from your brother or mother lately?” I asked.

“Yes, I have,” she said.

“I can’t believe we turned mom into a bisexual slut,” she said and then giggled.

“I know I can’t believe it either,” I said.

“Your brother?” I asked.

“I can’t believe Aunt Steph is letting him fuck her,” she said. “I guess mom must’ve told her about him, but I wish he’d find someone our age.”

“That’s what I told him,” I said.

“What was his response?” she asked.

“He basically said he’s having the greatest sex of his life with her and isn’t going to stop for inexperienced college girls,” I replied.

Sherry and I spent the next few weekends driving to see each other. We weren’t sure if we had a romance blossoming or if we were simply great friends with benefits. We agreed to date people on our own campuses. She said she had a couple of casual boyfriends, but none of them could satisfy her the way I did. I told her I found someone I could fall for who had a wonderful personality and was as great in the sack as she is but lacks in the BJ department.

When Thanksgiving break arrived, Sherry said she will only give handjobs to Rich. He still got to do anything and everything with Joanne. I told Joanne that I won’t fuck her anymore, I’m into Sherry and others my own age. That left Rich to be a true momma’s boy – fucking his mommy every way and every chance he got over the weekend. On the phone he told me about Joanne’s new kink so she can experience him fucking her missionary without having to look at him. She got into some mild BDSM and lets him tie her down and blindfold her before doing her missionary.

After Thanksgiving the rest of the semester was uneventful except for the occasional photo message from Rich of what his Aunt Steph was doing to him.

During semester break, Sherry and I spent every spare moment naked together. I told Sherry that although I wouldn’t fuck her mom, she could still have fun with her. That led to several sessions of me fucking Sherry from behind while she was on all fours eating her mom’s pussy to perfection. There were also several more times where Sherry blew me while she rode her mom’s face.

Rich on the other hand, stayed with his Aunt and was having sex with her multiple times a day. He said his aunt isn’t camera shy and would send me proof. He sent me a video of him being tied down to the bed and his Aunt Steph riding his cock hard as she held onto the headboard and leaning forward dangling her tits in his face. There was another video of his aunt deep throating him and yet another of him fucking his aunt missionary with her tits bouncing like crazy. When it comes to dirty talk during sex his aunt rivals Brenda James with how she tells him she’s going to cum all over his cock and how he loves it when she looks in his eyes while sucking on his cock.

I have to admit that I got turned on and jerked off watching these videos. His aunt is hotter than both Joanne and Sherry and watching her fuck rivals watching porn. I showed them to Sherry who got equally turned on. It led to some amazing sex between us. Seeing how much I liked the dirty talk, Sherry started using it on me. During one of these fuck sessions we planned to go out to Steph’s during spring break and double-team her while Rich watched. We agreed that we needed to experience Steph for ourselves.

A month into spring semester Rich told me for a fraternity pledge activity they had to streak past their bikini clad sorority sisters who would be rating their cocks. He said as he was running toward the girls he noticed two of the seniors with huge grins on their faces. They ran up to him and pushed him into the sorority house. They dragged him up a flight of stairs and tied him down to a bed. One was Anne, a busty green-eyed redhead with a nice round ass, the other was Debbie, a curvy blue-eyed brunette with DDD tits.

He said Anne straddled his face in a 69 while Debbie got between his legs to suck his balls and join Anne in giving him a double-team BJ. He told me that with all the pussy eating lessons he received from his mom and Aunt, Anne was moaning loudly and squirted all over his face as she orgasmed. He spoke about how they could both deep throat him, taking all of him in their throats and the feeling of two mouths and tongues working him over was indescribable.

Seeing how intense Anne’s orgasm was, Debbie demanded to switch places immediately. They did and he soon had Debbie orgasming on his face as he shot his load down Anne’s throat. They sucked him hard again before letting him up. He got to fuck each of them bareback doggie before pulling out and shooting all over their faces and breasts. He told me they were the two tightest pussies he’s ever fucked. Some of the other sorority sisters heard all the noise and watched from the door to see what was going on.

Over the next week he fucked the rest of the sorority, sometimes two at a time, before getting solo sessions with Anne and Debbie. His success with the girls led to his automatic acceptance into the frat.

“Joe my man, I should’ve listened to you sooner,” Rich said. “This is the best pussy I’ve ever had. Aunt Steph is disappointed I’m spending less time with her, but this is too good to pass up.”

“Tell your Aunt her niece and boyfriend are coming out to visit for spring break and there will be endless combinations to satisfy her,” I said.

“You guys are coming out?” Rich asked.

“Yes,” I said. “After the way you’ve been singing her praises and the videos you sent, Sherry and I need to experience her first-hand.”

“It sounds great, especially an opportunity to possibly tap Sherry again, but the Sorority invited me to join them on their trip,” Rich said.

“Tell them a family matter came up and you’ll join them a day or two late,” I said.

“Good idea,” Rich said.

When spring break arrived, Rich picked Sherry and I up at the airport and brought us back to his aunt’s large house which had an in-ground pool behind it. Steph was lounging by the pool when we arrived wearing a bikini top that barely covered the nipples of her 34F breasts and a thong bottom that was little more than a single thin piece of fabric that barely covered her pussy and ran between her butt cheeks leaving her ass exposed. She has bleach-blonde hair and blue eyes. I got hard in my pants just looking at her. I glanced at Sherry and saw she had a lustful look on her face.

“Why are you still dressed?” Steph asked when she saw us staring at her. “Strip down, it’s a clothing optional pool.”

We got naked quickly and grabbed a little surprise out of one of our bags. Once Rich was naked, we walked over to him and I pushed him down in a hair. Sherry straddled his lap and let the tip of his cock graze her pussy. I had gotten down on my knees and quickly put restraints on his ankles against the chair legs. Sherry grabbed his hands and put them in restraints on the armrests of the chair.

“Sorry bro,” Sherry said. “You don’t to participate until Steph has helped Joe and I reach at least one orgasm each.”

“Think you can handle both of us at once?” I asked Steph.

“If you two are as good as Joanne tells me you are, I can’t wait to find out,” Steph replied.

I laid down in a lounge chair and instructed Steph to 69 me. She straddled my face and laid across my body so she could suck my cock. Sherry was between my legs at the other end of my body so she could join in to give me a double-team BJ.

The things Steph was doing to my cock with her mouth and tongue felt amazing were indescribable as Sherry licked and sucked my balls. There were times when I felt their tongues dancing on the tip and shaft as if they were kissing each other around my cock.

But while they did that I got to try feasting on Steph’s pussy. Her lips were the poutiest I’ve experienced and her juices were the sweetest I’ve tasted as she got wet from licking her vulva, nibbling on her clit and fingering her pussy. She soon started grinding her pussy against my face, rubbing up and down, I had to reach up and grab her ass to hold her in place.

A few minutes later I heard her moaning how good it felt. Sherry told her we needed to switch positions because she wanted to watch me pound her while she rode Steph’s face. Steph climbed off my face and I stood up off the lounger.

Steph moved to a poolside table and laid across it with her head dangling off one side and her feet the other. She sat part way up and we looked at each other as I eased into her. I started with a slow steady stroke at which point Sherry straddled Steph’s face. She lowered her pussy to Steph’s face and laid her body across Steph’s so she could tease my cock as I slid in and out of Steph. I picked up the intensity of my thrusting and Steph wrapped her legs around me.

Pretty soon Sherry was moaning loudly at what Steph was doing to her at which point I lifted Steph’s legs onto my shoulders and started slamming into her as hard and fast as I could. The sound of our skin slapping together drowned out our moans. Sherry, seeing I was getting close climbed off Steph and got on her knees next to me, her mouth open and tongue out.

Moments later I groaned as I was cumming and the first blast went off inside Steph as I was pulling out, the second one coated her pussy lips before I could get my cock into Sherry’s waiting mouth for the rest.

When I was done, I helped Sherry stand up. She turned and bent at the waist to eat my cum off and out of her aunt while I went over and released Rich. In the blink of an eye Rich was behind his sister, rubbing his cock along her pussy before thrusting his entire length in quick and hard. The thrust caused her to lift her head from her aunt’s pussy and moan loudly.

“God sis, I’d forgotten how good your pussy feels,” Rich groaned. “Especially since you denied me at the end of the summer and Thanksgiving break.”

“Shit,” Sherry panted. “I’d forgotten how amazing your huge cock feels.”

Rich pulled Sherry away so he could continue to fuck her without distraction.

Steph and I just looked at each other before I offered my cock to her mouth.

Her lips and tongue were heavenly. Rich was right, her oral skills put Sherry’s to shame. The way her lips and tongue teased the head before taking my entire length in her mouth while her fingers tickled my balls was amazing. The way her lips applied just the right pressure was heavenly. I was rock hard in no time and soon had my hands in her hair as I came hard in her mouth. She swallowed my load before sitting up.

We moved to a chair and she sat in my lap her back to me as I reached around and fondled her breasts. We watched Rich and Sherry continue to fuck.

“Pull out we need to change positions,” Sherry moaned.

Rich pulled out and Sherry pushed him back onto a chair and then straddled his lap, facing him, guiding his cock into her pussy. She started riding him hard from the start. She was panting obscenities about how good he felt.

Steph was stroking my cock and licking my neck asking me if Sherry’s ever had DP because she wants to watch me fucking her niece’s ass as she rides her brother. I told her it only happened once with my cock in her pussy. Her hand and talk were amazing as I was rock hard.

“Go tap that ass,” Steph said. “I want to be licking cum out of two holes.”

I got up and went over to her grabbing her hips and licking her neck.

“Stop riding for a minute,” I said.

She stopped while fully impaled on him and I pushed her forward from the hips and guided myself into her ass. I started pumping into her and encouraged Rich to do the same. Pretty soon Rich and I were thrusting into her in synch and she was moaning loudly. I also heard Steph moaning and glanced over my shoulder to see her with her fingers buried in her pussy.

A few minutes later Shery shrieked “Oh my God! Yes!” as her orgasm hit. It was enough to set Rich and I both off as we groaned and shot our loads inside her.

“Bring that creamy goodness over to Auntie,” Steph said to Sherry, who staggered over and straddled Steph’s face. Sherry had multiple orgasms as Steph worked her tongue over her pussy and ass. They fell into a 69 and Steph was moaning as Sherry’s tongue worked its magic on her

After she came down from her orgasms Sherry came over and laid down next to me with her head on my shoulder. Out of the corner of my eye I saw Rich and Steph laying together, fondling each other.

“Joe, I’m sorry,” Sherry said. “I’d forgotten how good Rich’s cock feels. I need to fuck him again. I still love you, but I need his cock.”

“If that’s how you feel, go for it,” I said. “We said we could date other people while apart. I’m hurt and angry you want to start fucking your brother again, especially in front of me. You told him last year you were going to stop fucking him because of how you felt about me. But if fucking him makes you happy, I’m not going to stop you.”

“I’m sorry, but I’ve got to do it,” Sherry said, gave me a kiss and went over to her brother grabbing him by the hand and pulling him away from Steph.

I was upset as I watched them together, but Steph came over and blocked my view by putting her pussy in my face. I licked and fingered that sweet pussy until she was moaning. At that point she laid down next to me.

“Get in me big boy,” she said smiling with her legs spread.

I didn’t need to be asked twice and moved between her legs and entered her with one quick thrust. I started thrusting hard and fast and she ran her legs up my sides and locked them behind my back. She started her dirty talk, telling me how she was going to cum all over my cock. She was looking me in the eyes and running her hands over my back.

After a few more minutes I unlocked her legs and put them on my shoulders and started slamming into her harder and faster. She was moaning louder and our skin was slapping together loudly. That aural stimulation combined with the tightness of her pussy set me off. I pulled out and came all over her belly and tits.

An hour later we all had dinner together, but the conversation was uneasy as I was still bothered by Sherry and Rich together again. At dinner Rich said he was leaving in the morning to join the sorority sisters. Steph and Sherry said they were going to give him a double-team night to remember as a send-off.

I hung out poolside thinking about my relationship with Sherry and having some drinks so I wouldn’t be inside listening to them fuck.

I was getting drunk and I’m a lousy, angry, drunk, not a happy-go-lucky drunk. It was then that I decided that things were over with Sherry. Last summer she stopped fucking Richie because of her alleged feelings for me. While apart we agreed we could date other people so we could enjoy the college experience. But seeing her fuck someone else, especially her brother, right in front of me was too much. I also realized I want more out of a relationship than just sex. Although Sherry and I got along great, I realized we were more ilke fuck buddies than a couple. I also realized it might be the vodka talking and decided to wait until I sobered up to finalize my decision.

At this point it was around 11 pm and I stumbled inside and climbed into bed alone. I heard some laughs, muffled talking, and then moans and a banging headboard through the wall before falling asleep. A few hours later I was awakened by the sensation of a hand on my cock and my neck being kissed.

“Wake up,” Steph whispered. “Sherry wants alone time with Richie and I need more cock.”

“No,” I groaned. “I’m drunk, feeling miserable, and want to be alone.”

“Let me cheer you up,” Steph implored.

“No,” I groaned. I staggered up, grabbed her hand, pulled her naked body out of bed, and pulled her to the door pushing her out and locking the door behind her.

Now Steph is the sexiest, most skilled woman I have ever been with, and I was kicking her out of bed.

I managed to get to back to sleep, but around 4 am my stomach was churning. I barely made it to the bathroom before puking into the toilet. I rinsed my mouth out, found the Tyelnol in the medicine cabinet, popped two and staggered back to bed.

It was close to 8 when I was awakened again by a loud knocking on the door.

“Joe! Wake up! Richie’s getting ready to leave for the airport,” I heard Sherry calling.

I put on a pair of shorts and staggered out the bedroom door.

“Hey Richie, catch you later, have a good week with the sorority sisters,” I groaned as I looked up to see Sherry smiling hugging Richie.

“You look like shit, are you okay?” Richie asked.

“I’m nursing the worst hangover of my life,” I groaned.

“He got wasted pretty bad last night,” Steph said. “He turned me down last night, kicking me out of bed when I wanted sex.”

“Are you okay honey?” Sherry asked.

“Do I look okay you slut?!” I shouted and turned around, running to the closest bathroom to throw up.

After rinsing my mouth, I went back to the bedroom, locked the door behind me and laid back down, trying to go to sleep.

“Joe, I’m sorry, please let me in,” I heard Sherry crying as she knocked on the door.

I buried my head under the pillow trying to ignore her.

I heard her crying to Steph about something but couldn’t make out what.

I was hungover, I was angry, and I managed to fall asleep.