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Timmy's Girlfriend Joins In

My young friend Timmy's girlfriend wants to try bi and swinging.
I have written several stories about my activities with my young neighbor boy Timmy and his friend Scott, both eighteen years old. I helped them with their virginity and have taught them to have confidence with women. Their confidence seemed has grown with our “teaching” sessions.

It wasn’t long till Timmy got the nerve to ask out a girl and got himself a steady girlfriend. Her name was Debbie, a cute girl with long straight dark hair and from the pictures he showed me, she had breasts I was jealous of. Timmy told me that she was a bit of a nerd definitely not in part of the popular group.

I got weekly reports about his progress; Timmy went from first base to Timmy getting into her pants. Timmy was anxious for me to critique his pussy eating and give him tips. He figured that if he could make her cum good she might return the favor.

Timmy’s lessons in eating pussy paid off better than he expected. It was a good thing Debbie’s parents weren’t home when he showed her his talent. Timmy said that Debbie was yelling, “Oh God, Oh God,” as her whole body shook as she came. Debbie was so overwhelmed by her orgasm that she felt obligated to not only touch Timmy’s dick for the first time but she went right down putting Timmy’s cock in her mouth.

Knowing that the young couple’s next step was Timmy’s cock in Debbie’s pussy I pulled out a condom and told him he needed to know how to use it so he wouldn’t become an eighteen year old dad. We practiced putting it on and then practiced taking if off full of cum.

As Debbie and Timmy became quite the couple, Debbie introduced Scott to her friend Lauren. Lauren was a thin plain looking girl with long straight dirty blonde hair. Lauren was also not part of the popular group; she was also smart on the nerdy side. Scott and she were both on their first dating experiences.

Timmy was telling me that Debbie was encouraging Lauren to be more aggressive and enjoy herself with Scott. Scott got to second base quickly and was moving toward third. I showed Scott how to use a condom like Timmy figuring that he might need that knowledge soon.

I told both boys not to rush their girls and the girls would let them know when to make that big step to sex. Sure enough, both girls asked of the boys to go all the way. They would even double date and fuck in different rooms.

My biggest stipulation with the boys was that they never talked about our sexual arrangement with anyone. Timmy broke that agreement with Scott and to my shock, he let it slip with Debbie. He told me that he somewhat let it out to Debbie that Sam and I were swingers and that I was bi. He apologized but he said they were in the heat of sex when she brought up group sex and woman on women sex. He didn’t tell her everything; he just gave her some hints about our activities. He said she got excited and wanted to meet us and maybe have dinner with us.

Timmy looked down when he said dinner so I knew she meant more than just dinner. I glared at him and asked, “What is she expecting? A swap with us?”

Scott looked down again and whispered, “Well I’m not sure what she wants. She mentioned talking with you about trying bi and if it helps she is on the pill now.”

I told him, “Well look, I’m not promising you anything. I feel I have to talk with her now to be sure she won’t say anything. But you need to know she and I will have a long talk so I’m sure she knows what she is getting into. I will also have to talk with Sam, I’ve told you how big he is, she might be shocked.”

That night I told Sam what Timmy had said and what Debbie wanted. As I had predicted Sam was not happy that Timmy had talked but his very hard cock told me he was excited at the idea with I also predicted. “You’re such a horn dog all you can think of is fucking that cute little eighteen year old.”

“Hey fair is fair, he has been fucking my wife, shouldn’t I get to fuck his girlfriend,” Sam said.

“Stop right there big boy, if we do this, we do it my way. You don’t force it and you only do what I tell you and absolutely no anal.” Sam grunted yes and he fucked me hard. He was clearly excited as he pounded me.

Timmy brought it up again the next week telling me that Debbie kept asking if I had given him an answer. Feeling cornered I told him that we would set it up but I reminded him that I would be the one to decide if we did anything.

We picked a Friday night and I prepared a simple dinner. I was really surprised how nervous I was. At one point, I went to Sam and suggested that we cancel. He told me to just relax and if things weren’t right then we just have dinner and nothing else.

Timmy and Debbie showed up right on time. Debbie was wearing a cute skirt and a polo with her hair pulled into a ponytail. I was afraid to look but I was sure that Sam was already hard.

Debbie was clearly as nervous as I was, we made small talk as she helped me get the dinner out. It took a while but about half way through dinner, we were getting comfortable and relaxed. It was obvious that Debbie was a smart girl but still growing in confidence. Sam had wanted to have wine to get everyone to relax but I was not going to allow that, I wanted all the decisions to be made clear headed.

As we finished dinner, I suggested the guys take care of the dishes while Debbie and I had a private conversation. Debbie had a concerned look on her face but didn’t hesitate. We went up to our bedroom and sat next to each other on the bed.

I was very blunt with Debbie; I told her that I knew that she knew we were swingers. I explained to her that Sam and I felt that love and sex were not exclusive. Fucking is a physical activity and in our opinion can be done just for the sheer joy of it. Contrary to what my parents told me you can have sex with someone without loving them just to have fun. Debbie just sat there taking it all in without saying a word but her pointed nipples gave away her excitement. Her constant shifting of her legs told me that she was getting excited between her legs too. After my explanation I came right out and asked her what was she looking for?

Debbie shyly put her head down a little and said that she was just looking to explore new experiences. She said that fucking Timmy has been great but wants to try more, including her attraction to women. She was interested in our lifestyle, the group sex and the bi sex but she didn’t know how to go about it

I told her that I needed to be sure that this was what she wanted and that she was sure she knew what she was getting into. I told her that if we did show her swinging she needed to know about Sam.

Debbie leaned in with a concerned look, “What?”

“Sam is big, I mean bigger than Timmy. If you think he is too big, you don’t have to do it okay?”

Debbie just sighed and said, “Oh okay really?” and put her hands in her lap. I reached over and gave her a little kiss in the lips. Debbie sighed again and then reached over and kissed me back.

Our tongues met as we embraced. I pulled back for just a moment and asked her if she was ready to go farther. Debbie just nodded as I pulled my blouse off and undid my bra. Debbie was quick to do the same. I kissed her again and then moved to her tits. Timmy was right she does have nice tits. I sucked her hard nipples as she moaned and her hands found their way to mine.

Debbie moaned that it felt great; I took that as my cue to go farther. My hand moved under her skirt and found her very wet panties. As my fingers traced her pussy though her panties; Debbie lay back on the bed. I pulled her skirt and panties off exposing her timed little muff. I pulled my skirt off and my panties off before I moved down to Debbie’s pussy. Debbie shuddered as my tongue slid across her pussy lips. I stopped for just a moment causing Debbie to moan, “Please,” and arch her hips up to my lips. I drove my tongue into her cute pussy finding her clit licking it hard. It wasn’t long before Debbie was moaning rather loudly that she was cumming. Timmy wasn’t kidding that she got loud when she came.

After her orgasm, I kissed her with her juice still on my lips and asked her if she was ready to taste me. Debbie again just nodded. We traded places and I lay back spreading my legs. Debbie quickly commented how pretty my shaved pussy was and maybe she should shave hers. She hesitated just a moment then pushed her tongue into my pussy. Debbie was a little sloppy but was getting the job done. Debbie’s loud cumming had drawn the boys’ attention.

The guys walked in while Debbie’s tongue was exploring my pussy. I pulled her up to me and told her that the boys needed a little attention. Debbie covered herself a little embarrassed that she was naked. I told her rather than covering up she should help the boys off with their cloths. “I will help Timmy out if his, why don’t you see what is in Sam’s pants.”

I led Debbie over to Sam and put her hand on his pants. She rubbed his crotch and said, “Oh shit.” Debbie fumbled with her pants but got the belt undone and unsnapped his pants. They fell to floor with his dick sticking out of his boxers. Sam pushed them to floor and stepped out of them. Debbie turned to me and mouthed the words, “It’s big.”

“Debbie, are you sure you’re ready for it?” I asked.

Debbie didn’t say a word, she just leaned in and kissed the head of Sam’s dick.

By then I had Timmy’s clothes off and was stroking his hard cock. I got up and went over to Debbie and told her to take it slow, “I’m going to take Timmy in the guest room so you and Sam can have some privacy.” Debbie was attempting to put her mouth around Sam’s cock as Timmy and left the room. I kissed Sam and told him to go slow with her.

My pussy dripping by then and really needing to cum. I quickly lay on the bed and told Timmy to get in me and fuck me hard. It wasn’t long after Timmy jump up and began to pound my pussy we could hear Debbie calling out that Sam’s cock felt so big inside her. “Oh Fuck, Oh Fuck I’m cumming,” Debbie screamed. I knew Timmy was close but Debbie calling out pushed him over the edge.

Timmy grunted and shot his load in me. I pulled Timmy into me and asked him if he wanted to watch Sam finish in Debbie. Timmy nodded yes got up and moved down the hall back to our bedroom.

Debbie was on her hands and knees on the bed and Sam was standing behind her slamming his cock into her pussy. I could tell from Sam’s face that he was getting close to cumming, so I moved in front of Debbie and started kissing her. I knew that would drive him crazy. It had the same effect on Debbie as she began to moan again. Sam grunted as he exploded in Debbie’s young pussy. Sam pulled out as Debbie collapsed on the bed.

I kissed Debbie again and said, “It looks like my husband has made a big mess between your legs. I better get down there and clean it up.” Debbie didn’t say anything, she just moaned as I played the cum oozing from her pussy and moving my lips to lick it up

As I was eating the cum from Debbie’s pussy, I could hear Sam behind me tell Timmy to “Go ahead she will like it.” Figuring that Timmy was getting excited and hard watching me eat Sam’s cum from Debbie, I shifted my legs and hips to give Timmy access. Although I kept my concentration on cleaning out Debbie’s cum soaked pussy, I felt Timmy’s weight move the bed and then I moaned loudly as his dick slipped inside my pussy

“Debbie I think your pussy is cleaned up and Timmy’s cock feels great in my pussy right now, you ready to take my husband’s cock back inside you?”

“Oh yes, I would love to fuck him right next to you,” Debbie said and she slid next to me in the bed.

I rolled over so we were side by side, with the boys getting between our legs. They entered us just about simultaneously as Debbi and I both moaned. Debbie and I traded some dirty talk about how great boys cocks were inside up side by side. Debbie came first, and then Timmy and I came followed by Sam shooting his load into Debbie.

As we lay there on the Bed Debbie spoke up, “You know Lauren and Scott would love this.”

“Oh shit does Lauren know too?”

“Sorry Lauren and I were comparing notes about fucking and I told her we were meeting you guys. Sorry but She really wants to try it too,” Debbie said with a smile.

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