Sex stories

Adventures of the Cherry Pooper. Gretchen, or: how we (almost) completely stopped having fun

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Me and Dana were turning 30 this year. We were married for 7 years, just had our second baby, and Dana was seriously considering having another child.

But we kept fucking other women, mostly together. Usually Dana was the one who initiated it. We took protection seriously, used condoms regularly, always asked if our partner was taking pills. We didn’t want another Jada incident.

Speaking of Jada, my older son was a beautiful brown 7 years old. He lived with his mother, I invited him for family vacations and holidays, but without his mom.

Jada was in her third serious relationship, another low life man who would knock her off and run. Without my help she wouldn’t be able to afford living. I kept my opinions to myself, I didn’t want any unnecessary touch with her. My son grew up in a hard neighborhood, but I was watching to see he got what he needed. When the time comes, he will know he can always trust his father for help.

But this story is not about Jada or my son, it’s about Gretchen. She was the opposite of Jada, rich woman, good education, good job. Blonde hair, large, implanted tits, always looking good, dressed smart, wearing the right makeup and smelling the right perfume.

Dana met her on her job, and immediately had a strong connection to her. For a time they were going to lunch on regular basis, talked a lot on the phone, they became best friends.

Dana have her way to get people to talk to her about the most intimate things, and with Gretchen it was not different. Gretchen told Dana she was frustrated from her sex life, she scared off the guys she wanted, she was to good, to successful, to rich, to pretty, somehow she couldn’t get dates, and if she got one, the guy wouldn’t stay around much.

Dana was curious about Gretchen sex experience, which wasn’t much. Dana was happy to teach Gretchen that sucking cocks was indeed quite fun, if done right, and yes, her ass is a valid place to get a dick in. Dana helped Gretchen order some sex toys, to help her practice her skills.

Eventually Dana got tired of explaining, and invited Gretchen over for Sunday, when we both can teach her how it’s done. We had to hire a sitter for the kids and order a suite in a hotel, to get enough privacy for one Sunday fun.

Saturday night we checked in the suite, and called Gretchen to come in. It was the first time I actually met her, and she was a bomb! She’s what my type of men would classify as 9, most guys would score her a perfect 10.

As she walked into the suite, dressed in a black night dress, her bra and thong visible through, her hair glows, her smell fill the air, my very primate scense told me this is a woman to grab and not let go.

We sat and had light dinner, with a bottle of champagne. Dana didn’t let Gretchen’s glass get empty, and soon enough Gretchen got a bit drunk.

Dana turned the discussion to sex, to our private life, to what we are going to do. She asked me to get naked, which I did, than she ordered me to stand between them, and she took me in her mouth, getting me hard and ready.

Dana released me from her mouth and offered my hard cock to Gretchen. Gretchen took it in her mouth, and Dana advised her how to do it. She wasn’t good at all, but I played my part, rolled my eyes and moaned, while Dana calls her «wow you do it amazing! You are natural at that!»

But soon I got tired of being bitten in my dick, and only kept it hard on sheer will power. I started to understand why guys would run away from her.

Dana saw it and changed direction. She grabbed me and we went to bed. Dana quickly took her clothes off, and invited me to fuck her pussy, which I gladly did.

Gretchen looked at us going on, Dana was staring at her as she came again and again. Eventually I felt Dana’s body giving up, she had enough for now. I pulled out, my dick hard and shiny from Dana’s love juice. Dana invited Gretchen to replace her with me. Hesitant, Gretchen finally took her dress off, revealing the work of art her body was. Light color, slim, big breast. Sexy.

Gretchen laid beneath me and spread her legs. She wasn’t shaved at all down there, big turn off. Seriously, she invested so much in looking good, just 10 minutes with a razor would make it perfect! Why neglecting this???

Anyway Dana remembered and quickly pulled out a condom. She rolled it on me, holding my dick on her opening, stretching the tension to max.

When I finally pushed into Gretchen body, she moaned loudly. Dana played with her perfect nipples as I fucked Gretchen’s pussy. It took only a minute till Gretchen started Cumming.

Gretchen was Cumming loud, but felt fake, she barely moved, and frankly, felt like fucking a sleeping, or dead woman.

Looks: 10. Fuckability: none so far.

I pulled out and lifted Gretchen’s legs high and wide. Placed my dick on her rear entry, in attempt to get into her back orifice. She shakes and locked, clearly terrified. I had not had such an unpleasant fuck in years! Virgins were more enthusiastic than this poor girl!

To relax her and show her it’s alright, Dana stood on 4 and asked me to fuck her ass first. I gladly obliged, not even removing the condom, just went straight to Dana’s warm ass. Her moaning got louder and louder as our fucking got more and more intense. Dana had a full body orgasm, shaking her entire body in pleasure.

The look of Dana Cumming so hard convinced Gretchen to try. I put on a new condom, and tried to get into her ass.

She did practice dildos and butt plugs, as I finally broke her resistance and penetrated her anus, she was easy going and let me slide in easy. It took some efforts to get her to cum though, and she just couldn’t let herself enjoy her full potential and just cum hard.

I was frustrated, turned out I really need my partner to seriously enjoy, or I wasn’t enjoying too. After two minor orgasms I pulled out of Gretchen ass, decided that’s enough.

I pilled the dirty condom, to my surprise Gretchen stayed on 4, playing her pussy, now she wanted to get fucked!

I didn’t think much of this, just came back and pushed my hard dick into Gretchen’s pussy. She was wetter, warmer, she came faster and harder. Its like something in her head suddenly clicked, and she started enjoying.

Orgasm after orgasm, I fucked Gretchen in doggy style. I felt my peack, after holding long time trying to please her, she finally reached the goal. I felt my orgasm hit me, and to slowly pulled out of Gretchen’s pussy to shoot on her back. Dana licked my cum off Gretchen’s back, and showed me how she swallowed. Exhausted we went to sleep.

I woke up early as ever, and went exercising. Returned some time later and ordered coffee and breakfast.

While I was eating I heard noises from the bedroom. I finished my coffee and went to see the commotion.

Dana and Gretchen were fucking. Gretchen was laying on her stomach, and Dana pushed two lubed fingers up Gretchen’s ass, and the other hand played with Gretchen’s pussy. Gretchen was Cumming loudly.

I took my clothes off and kept standing there, watching. Jerking myself to get hard.

Dana noticed me, and when Gretchen needed a second to breath between her orgasms, she invited me to come and fuck Gretchen’s ass. I didn’t need a second invitation. Dana lubed me and I went straight into Gretchen’s ass, deep in.

Gretchen noticed me, she was already warmed and ready, and started Cumming in no time. This time proper, strong, anal orgasms.

I felt she couldn’t hold any more and pulled out. My dick was dirty from Gretchen’s ass, the only place I could use it now was Dana’s ass.

Dana laid on her back, lifted her legs up and spread her ass cheeks with her hands. I lubed myself and penetrated Dana’s back entrance. I know Dana well, I know how her body loves it. We moved together, to the goal of making Dana cum.

Gretchen came and kissed Dana, while I was fucking her. It pushed Dana to her first top, she came twitching and screaming.

Gretchen moved to Dana’s tits, while I kept fucking her ass, and Dana was pushed to a second, and than third orgasms. I felt the routine, I knew what Dana wanted now, and I was determined to give it to her.

I kept pushing Dana’s body to a fourth, stronger orgasm. I signaled Gretchen to put her head on Dana’s clit and lick It. Gretchen did so, and Dana got over the top, shaking wildly and screaming she came harder than before. I knew what would happen, Dana fainted in the top of her orgasm. Gretchen didn’t notice. I pulled my dick out of Dana’s butt and exploded on Gretchen’s perfect face. Her pale face were filled with strings of my warm, gooey cum. She didn’t know what to do, she looked at Dana for a clue, but Dana was blown out.

«This is my cum.» I said «this is my ultimate gift for you. Accept it with love and grace, insert my cum in your body!»

Gretchen was confused. She laid back, opened her legs, and tried pushing my cum with her fingers into her pussy. It was funny, and it got her to cum again.

I waited she would relax and explained » I wanted you to swallow my cum. But you handled it well anyway. »

Gretchen looked at me exhausted, smiled wordlessly. I just turned and hit the shower.

I do hope we helped Gretchen get over her sexual frustration, because after that weekend we weren’t in contact for a month. After a month Dana had lunch with Gretchen, who told Dana her period is late.

Dana sent Gretchen to take pregnancy tests, she was positive. Dana was furious! We didn’t need another surprise child in our life!

But Gretchen decided to keep it. I promised I wouldn’t be the abandoning father, I took responsibility for my children, but Gretchen was a different story than Jada. She lived way more expensive lifestyle, and had more demands of me. One of them was to regularly meet me alone. It was obvious she was trying to get between me and Dana. Dana wasn’t willing to give me up, and I sure didn’t want that. It ended up with lawyers, almost in court. But her lawyer admitted she asked to much, and we settled on living allowance. I didn’t promise education, though I knew I would give it in time. But I was so angry at her, I tried to get as much as possible out of her hands.

For a long time after Gretchen, Dana didn’t invite anyone to our bed. She got burned twice and didn’t want it to happen again.

Eventually we found the safe route. Dana started focusing on more mature women, preferably married. Women who couldn’t, definitely wouldn’t get pregnant.

We occasionally slipped and sinned with younger women, usually at vacations we took abroad, where the woman definitely couldn’t be hooked to us after. But mostly, we were very careful with whom we went to bed with.

Next time, if you would like: how Dana got over her fears, and I got married the second time. Upvote if you want to read the story.

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