Experimenting with Penny

This story contains sexual acts including oral sex, anal sex, threesomes, cum eating, toy play, and some guy on guy sex. If any of this offends you, you have been warned. If you have an open mind, please enjoy and let me know what you think.

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Penny and I have been dating for a long time now. Like every couple, we started things out slowly with everything. It was always a battle to decide what movie to go see, where to eat, or what else to do. Unfortunately, sex was the same way. The sex was great, don't get me wrong, but it was always the same. We would start out with oral sex now and then, but it was pretty much missionary position during sex. She had a pretty bland past when it came to sex, and was hesitant to bring new things up because of the way her ex-boyfriends made her feel about it. I have been lucky, I guess, and most of my exes were very experimental in bed.

After some time, I began to slowly share some of my exploits with her in an attempt to get her to loosen up, and to show her it was ok to enjoy sex. I started off mild by telling her about some of my first experiences in anal sex, and using toys on my exes. As she began to feel more and more relaxed, she started to trust me enough to open up too. I still remember the night she came out, and started asking me questions about anal sex. I could tell she was interested, but until she asked for it, I was not going to press the issue. I wanted it to be completely her idea, and the last thing I wanted was to scare her back to being guarded. As time went on, we talked about it more and more. With each conversation about it, she got more and more excited. Finally, she timidly told me she wanted to try it.

"Ok, I kind of want to try anal sex." She said. "But, I am afraid of it hurting."

"We will use plenty of lube, and I will go really slowly. If it starts to hurt, just let me know and I will wait for you to adjust." And, we did just that.

She and I both really enjoyed everything that lead up to me taking her ass for the first time. I took my time loosening her up with a well lubed finger before I even started trying to slide my cock into her. The whole night seemed to last forever as she lay over the side of my bed, and took inch after inch of my cock until I was finally inside her. Eventually, she was relaxed enough for me to fuck her without hurting her. I continued fucking her ass until I was ready to cum, and I buried my cock inside of her and emptied my balls. To this day, she still enjoys me fucking and cuming in her ass.

Since our first time went so good, I began to share more things with her. I told her about using toys on my exes while I went down on them, about one using a vibrator on my ass as she sucked my dick, and eventually, I told her about one ex that used a strap-on on me. Every time I shared something new, we would end up talking about it for a while before we incorporated it into our sex life. It was always the same with each new topic. I would bring a topic up over a heated conversation through text messages or instant messaging. Soon, we would begin fantasizing about incorporating our new idea into our sex life. Eventually we ended up incorporating everything from my past, and things one or the other of us just wanted to try.

The first thing I got to experience for the first time with her was eating my own cum. During one of our chat sessions I brought up a time where I accidently tasted my cum when kissing down a girlfriend's body after she had been sucking my dick. As I kissed back down her body, I tasted something on her chest. It took me a second to realize I had just ate some of my precum off of her. Rather than being grossed out, it turned out that the idea strangely excited me. I never could get up the courage to ask a girl to try it with me, but Penny helped me through that.

"I noticed that you never had a problem kissing me after you came in my mouth."

"Not at all." I said, trying to come off as confident. "I actually look forward to kissing you after. There is always the taste of cum left in your mouth."

"I'm sorry." She said. "I try to make sure I swallow all of it so you don't taste it."

I assured her it was ok, and this led to her asking me if I would like to try more of it. We talked and talked about different ways I could try more, and the way that turned us both on the most was for me to lick it off of her breasts. She loved me giving attention to her nipples and breasts anyway, so this was a win for the both of us. The next time she was giving me a blowjob, I had her lay on the bed while I stood beside it. She sucked my dick like the many times before, but this time I pulled out just before I got ready to cum, and I sprayed my cum all over both of her D-cup breasts. I quickly bent down and began to slurp all of my cum off of her chest. Mouthful after mouthful, I swallowed every bit I scooped up until her chest was free of any cum. Much like anal sex, that was not the last time this was to happen. We even tried multiple other ways of me eating my cum, to include her spitting it back in my mouth after a blowjob and me eating it from her ass after cuming inside her.

After that experience, it was just about free game for trying new things for either one of us. As the weeks and months went by we bought an assortment of dildos and vibrators to include in our play. Every new idea that one of us came up with that we wanted to try was just like the first time all over again. We would spend days and weeks texting, chatting, and emailing details back and forth. It was always easier for us to share if we didn't have to actually say it out loud.

As we got used to involving the dildos and vibrators into our normal play, we began to consider pushing things to the next step. I liked seeing the dildos slide in and out of her pussy while I was sucking on her clit, and I knew Penny liked the feeling too. One day I finally brought up the subject of bringing another guy into our play.

"You know how we like using the dildos?" I asked. "Have you ever given any thought to having a threesome with another guy?"

"Sure, I mean ... I have thought about it, but I don't know ..." she hesitantly responded.

From there, we began to talk about it in the majority of our conversations. We even acted some out while we were having sex, with the dildos playing the part of the other guy. I told her things that I wanted to try, and she shared things that sparked her interest. I wanted the guy to fuck her from behind while she and I were in a '69' position with me sucking on her clit. I wanted her on her knees in front of us sucking both of our dicks. I also wanted to eat his cum off of her body. She liked being filled up, and she wanted to be sandwiched between us with him fucking her ass while I fucked her pussy. She also wanted to be fucked from behind while the other one of us fucked her mouth. Eventually, we actually got up the nerve to post a Craigslist add to find the right guy.

Over the course of a couple weeks, we narrowed down an overwhelming response to one guy, John, that we thought would be the best fit for us. We sent pictures back and forth along with emails detailing what we were interested in, and he did the same. John was around our age, in decent shape, but was pretty much average, just like we were. From the pictures he sent, his cock was about the same size as mine, so we knew she would have no problem taking it up her ass. The three of us decided to meet the following Friday for dinner, and move our party to a local hotel room for the rest of the night, and maybe the weekend.

We all dressed casual to make sure that we were comfortable with one another before we jumped into things. We got to the restaurant a little bit before John, and were already seated by the time he arrived. Since Penny was already sitting when he got there, John simply sat down beside her when he joined us. We were a little bit nervous about everything, so dinner started with everyone ordering an alcoholic drink to take some of the nervousness off, and it worked perfectly. We chatted throughout dinner as though we were just friends hanging out, but we all knew exactly what was going to happen later. By the time dinner was over, we were all comfortable with each other enough that we were ready to hit the hotel room. John followed us over in his car, which gave Penny and I time to talk about it.

"So, are you excited?" I asked her.

"I am very excited, but I am still a little bit nervous."

"It's ok; I think everything will be fine once we are in the room together." I said, "I can't wait to see you taking both of our cocks!"

"Ooo, that sounds nice baby."

We were only ten minutes away from the hotel, but it seemed to take forever to get there, with what was planned. We had already checked into the hotel earlier so we wouldn't have to stop at the front desk on this trip in. John pulled in and parked beside us, and we all headed up to our room. As we entered the room, Penny excused herself to the bathroom to change into the lingerie I picked out for her earlier. I mixed us all another drink while John and I chatted, waiting on her to return. We took a seat on the couch with our drinks a few moments before Penny came walking out of the bathroom. She was wearing a black and purple bustier that drew attention to her 36D breasts. Below that was a matching thong, and garter belt attached to black thigh-highs. Topping off the outfit was a pair of shiny black high heels that made her calves and ass look amazing as she walked across the room.

I could feel my dick growing hard in my pants as I watched her approach us on the couch. I almost forgot about John being there until I felt him shift on the couch too. He was obviously becoming aroused by her appearance also. She didn't say a word to either one of us, and simply took a seat on the couch between us, as if nothing was out of the ordinary. As we sat speechlessly, she picked up her drink and took a sip.

Finally, John broke the silence. "You look amazing!"

"Thank you!" she replied. "But, I feel a little underdressed with both of you still fully clothed."

With that, I told her she should help John get out of his pants so his cock would have room to grow. I watched as Penny and John stood up in front of the couch and began to caress each other. Penny began moving to her knees as she fumbled with John's belt and zipper. She pulled his pants and boxers down in one motion to let his cock spring free. She wrapped her hand around his growing cock, and slowly started to stroke it. She looked at me as if to ask for permission before moving forward to take it into her mouth. I nodded, and watched as she worked every inch of his dick into her mouth before moving back off of it. Once it was completely hard, his dick was about 7 inches long, and was fairly thick.

I watched her for a moment before standing up and removing my clothes as well. I walked up beside them and pushed my dick into her view. She knew I wanted her to suck it, which she was happy to do. With both of our dicks hard, I told her to move to the bed so we could continue playing.

I had her pull her panties off before putting her on her back on the bed. She propped herself up on a couple pillows and resumed sucking John's dick while I moved between her legs. I nibbled and licked the inside of her thighs, making my way up to her already wet pussy. She gasped around John's dick when my tongue finally made contact with her excited clit. As I tongued her pussy and clit, I looked up her body to watch her alternate between sucking his dick and his balls. She would suck each ball one at a time while she continued to stroke his dick. Her saliva coated the entire length, making it shimmer in the light. I continued to eat her pussy until I felt her body tense up and shudder from her first orgasm of the night.

As she came down from her orgasm, I moved from between her legs and lay on my back on the bed so she could ride my dick. She crawled on top of me and sank all the way down on my dick in one quick motion. We kissed passionately as she slowly started gyrating on my dick. John took this as his cue to get ready to fuck her ass. He moved around us, and I could feel him moving into position behind her. He got on his hands and knees, and let a little bit of his saliva drop onto her puckered asshole. I knew right away, he would soon have his tongue buried in her asshole. I reached around her and spread her cheeks open to make it easier for him. He began his assault on her ass with his tongue, just like I had worked on her pussy.

I lost track of everything until I felt him moving again so he could fuck her ass. My entire focus moved to what was happening behind her. I made sure to keep her ass pulled wide so his dick would slide in easily. Then, I felt the head of his dick sliding around my fingers as he started pushing it against her hold. I held still as I felt him start to slide into her ass. I could fill his dick sliding next to mine as it made its way in.

It was an incredible feeling that I could never begin to describe. Even though we had done similar things with our dildos, there was no substitute for knowing that it was a real dick sliding into her with me.

We quickly fell into a rhythm of fucking her. As he pulled out, I pushed in. And, as he pushed in, I pulled out of her. We fucked her hard for several minutes, and were able to give her a second orgasm. This one was even stronger than the first, and I have to assume it was due to her pussy and ass being filled with cock.

After a bit, John moved onto his back so that Penny could ride him while she sucked my dick. I grabbed the side of her head, and fucked her mouth, occasionally making her gag slightly on my cock. After all of the stimulation, it didn't take long before I was ready to cum, but I didn't want to cum in her mouth. Without John stopping, I quickly moved behind them and slid my dick all the way in her ass in one quick push. A few pumps later, and I slammed deep inside her as I began to cum.

As my dick began to shrink, I had John stop fucking Penny so she and I could get into a '69' position. She didn't have the concentration to continue sucking my dick, but I quickly latched onto her clit while John started sliding back into her pussy. I knew he wouldn't last long, so I worked hard on her clit as he slammed in and out of her pussy. As he fucked her hard, it caused my cum to start leaking from her ass and running around his dick. As it started to run under her pussy, I began to lick and suck it up off of them. I watched as his balls began to draw up in preparation for his quickly approaching orgasm. He pulled out of her and began jerking his dick within inches of my face, aiming it at her ass and pussy. His first shot of cum sprayed across her ass and quickly started to run down as he continued cuming. His remaining shots landed on her ass, her pussy, and my face. When he was finally done, her well fucked pussy and ass were coated in cum, along with some of my face. He then moved down to start licking her cum covered ass while I continued to work on her clit. Our licking was enough to push her into one more orgasm before she finally collapsed on top of me.

Exhausted, we moved so that we could all lie on the bed with Penny in the middle. Her lingerie was spotted with cum and sweat, but it was an incredibly hot reminder of everything we had just done. I drifted off to sleep replaying everything over and over in my mind, but I knew I wanted more after I was rested. At that point, I could only hope that Penny would as well.

The next morning I woke to find Penny and John already gone. I heard the water running in the bathroom, and assumed Penny was cleaning up. In a few minutes, I found out I was wrong when John came walking out of the bathroom in only a towel.

"I hope you don't mind," John said. "I wanted to wash up a bit."

"Not at all. In fact, I think I will do the same thing." I replied. "Make yourself comfortable."

As I washed myself clean in the shower, I couldn't help but think of last night. My dick started to grow hard while I was daydreaming, but my focus returned when I heard the door shut to the room. I finished rinsing myself off, and started getting out of the shower. After the water was turned off, I started hearing some noises coming from outside the bathroom. I quickly realized that the sounds I heard were of Penny and John grunting and moaning. I wrapped a towel around myself after drying off, and exited the bathroom.

The sight that welcomed me when I walked out of the bathroom was incredibly hot. John had Penny's hands held behind her back, her pants were around her ankles, she was bent forward with her chest pinned to the wall, and he was already pushing his dick into her pussy from behind. He was pounding into her hard with every stroke. With his free hand, he would hold her hips steady, and occasionally slap her on the ass.

I watched for a moment before I couldn't resist joining them. I made my way between Penny's legs so that I was sitting on the floor between. I began sucking and biting her engorged clit as John kept slamming into her. Every time he pulled out of her, her pussy lips grabbed and pulled at his dick as if trying to keep it inside her. I reached up under her shirt to find her erect nipples. I pinched and pulled her nipples as her breasts bounced with his thrusts. We continued our assault on her body until I could sense her impending orgasm. When she started to quiver, I latched onto her clit and sucked it hard. John's dick was soaked in her cum as he continued to piston in and out of her. With his pace quickening, I could tell he wouldn't last much longer. I began to lick the bottom of his dick as it slid out of her pussy to help push him over the edge. A few more thrusts and his cock started twitching inside her pussy. I knew he was pumping a big load deep inside her.

After he finished cuming inside her, John simply pulled out of her and walked away. As soon as he pulled out, Penny's gaping pussy began to leak their cum. I quickly started licking and sucking her pussy to get every drop of his cum out of her. The combination of their juices was amazing sliding down my throat.

After I finished cleaning her up, I led Penny back to the bed to catch her breath. As she was laying on the bed, John crawled up beside her while I got the coffee and doughnuts that Penny had evidently brought back for us. We all reclined on the bed enjoying our breakfast, and chatted about nothing at all. We played off and on the rest of the day before John had to leave us.

A few weeks went by where Penny and I would reenact the different things we had done with John, but there was one topic that never came up until she finally texted me about it. This was about how John all but jumped her when she came back with the coffee and doughnuts.

"You remember how John was fucking me when you came out of the shower?" She texted me.

"Yeah! That was incredible. What about it?" I answered.

"Well, ... I was really turned on by it."

She didn't really have to tell me that as I could tell it as soon as I slid between her legs then, but I knew there was something more on her mind. So, I allowed her to continue. She went on to tell me how being restrained by him while he fucked her like that was an amazing feeling for her. I knew right then that we had a new topic to experiment with.