Old Girlfriend

I was struggling with my thoughts about what had happened with John and deep down I wanted to be with a girl, especially since I never had, and so I needed to see if I still had thoughts about being with girls, and decided to try hooking up with an old girlfriend. I really needed to see if I still had feelings about having sex with girls and I hoped that just maybe my experience with John gave me more confidence, so I had to see if could have sex with a girl.

We had been close before and when I contacted her, she seemed eager to go out. Her name was Sheryl, she was short, had sandy brown hair, and even though she was petite, she was still a little heavy, but she had a pretty face, great eyes, and was known to be a little easy.

Any way, we hadn’t seen each other for quite sometime but immediately we made arrangements to go see a movie.

I was nervous about what would happen, but I felt I needed to push it and try to get in her pants somewhere along the way, but why was I feeling this way.

Anxiously, I picked her up, and smiling she said hi, as she got in the car. We shook hands and embraced over the centered console, and exchanged pleasantries. As we headed toward the theater, she told me she was surprised to hear from me and said that she had thought about me and that she was glad I contacted her.

In the theater lobby, we grabbed a soda to share and some popcorn before we headed into the theater. We decided to sit up near the top, but it didn’t really matter where we sat, there weren’t a lot of people there. We talked about nothing in particular and when the lights started to dim, Sheryl grabbed my hand, which made me look at her as the theater went dark, and as our eyes met, she squeezed my hand.

I felt that I really had a chance to have sex with her; all I needed to do was go for it, and as the movie progressed, I eventually lifted the arm that separated us, and put my arm around her. As I did, she snuggled against me, putting her head on my shoulder.

When the movie ended and we headed out of the theater, Sheryl took my hand as we were walking; it was nice. In the car, we talked about the movie and when there was a lull, Sheryl asked me if I wanted to come over to her house for a little bit. I was nervous but when she suggested that we could watch TV, I felt more at ease and when she also said that her folks were out of town, I immediately said, “Okay.”

Sheryl smiled at me and squeezed my hand, I could tell she was obviously excited and when we eventually pulled up front of her house, it was late. We hurried inside, sat down on the couch, in the living room and as she fumbled through the channels, looking for something to watch, she asked if I wanted anything to drink. I was hesitant but asked, “What do you have?”

Sheryl said, “I’m not sure, let me check, but I think there are a few beers in there,” as she stood up and headed into the kitchen.

I simply replied back, “That sounds great.”

She returned rather quickly with two beers and as she handing me one, she sat next to me. We watched a movie on TV for a while and I think she was waiting for me to make a move when I was hoping she would make the first move and I think she was becoming inpatient

Sheryl then said, “I’ll be right back,” as she headed down the hallway.

I didn’t know exactly where she went and figured she must be using the bathroom so I waited there patiently, and it wasn’t long before I heard her coming back. When Sheryl came around the corner, she was wearing a T-shirt and some cutoff sweatpants, and said, “I hope it’s okay, I wanted to get more comfortable,” and as she past by on her way to the kitchen Sheryl asked, “Do you wanted another beer,” in which I quickly told her yea.

When she returned, she sat right next to me and as she handed me a beer, she kissed me on the cheek. I was taken a back and as we looked at each other, I asked what that was for. Sheryl said thanks for taking to the movie and thanks for asking me out.

I needed to do it and so I leaned into her and we kissed again, and as we continued to kiss I felt her boobs as our tongues continued to dance as we kissed. Eventually, my hand went up the back of her shirt, quickly unhooking her bra. She hesitated briefly but we instantly continued to grope and feel on each other. Now that her bra was undone, I moved my hand to feel on her boobs.

She felt firm and her little nipples were hard, which continued to excite me. Sheryl laid back on the couch and as I went to my knees in front of the couch, and we continued to kiss, I could tell Sheryl was kind of taking the lead, which I needed. She untied her sweatpants, and pulling them down slightly, she took my hand and put it down the front of her sweats. She was wet and feeling her pussy made me even more horny to try to fuck her, and I think she wanted it too.

When we stopped for a moment, Sheryl pushed me away slightly and tried desperately to undo my pants again, wanting to see and feel my cock but when she was unable to get them unbuttoned, she quickly tried to take my shirt off, which I happily obliged.

Sheryl started to passionately feel on my chest and when we went back to kissing, I tried to take her shirt off too, but she stopped me, pushing my hand away. I was confused but then she whispered, “Let’s go to my bedroom.”

We quickly both stood up, she adjusted he sweats and taking my hand, she lead me toward her room. I became apprehensive not knowing if I could do it, but I also realized it was now or never and so once in her room, I tried again to take her shirt off and as I pulled her top over her head, Sheryl again tried to undo my pants.

I quickly helped and as I let them fall to the floor, Sheryl felt on my cock through my boxers. I was hard and almost immediately, she took them down and started to rub my cock. Sheryl was so horny, she took off her sweats and as we went back to kissing, all I could think about was wanting to fuck her.

We moved over to her bed and as she sat down, Sheryl took hold of my cock and started to suck it. It felt good and I remembered when John had given me a blowjob, and how it felt. I laid her back and as I did she asked , “What’s wrong.”

Nothing was wrong, I told her, and I thought to myself that I didn’t want to risk going soft as I did when John sucked my cock, and so I climbed on top of her and when we started kissing. I fingered her wet little pussy, grinding against her leg. I wanted to fuck her and as Sheryl groped to feel my cock, I obliged her by moving up so she could feel my cock.

I continued to think about John and how it felt, but I wanted to fuck Sheryl; we were so close to doing it. I spread her legs as I fingered her pussy and moving between her legs now, she gasped as the tip of my cock touched her pussy. Sheryl lend up, kissing me and as she did, I tried to push into her, wanting to be in her. But suddenly she stopped me, pushing me away saying, “We need to use protection.”

I was confused but when she asked, “ Do you have a condom,” I knew what she meant, but I didn’t have one.

I told her, “No, I don’t.”

Sheryl quickly said, “There’s one in the bottom drawer,” pointing to her dresser.

I quickly got off the bed, and as I did, Sheryl said, “Nice ass,” as I bent over to look through the bottom drawer of her drawer.

Immediately, my cock started to go limp, and as soon as I found her stash of condoms, I quickly grabbed one, and returning to the bed Sheryl remarked, “What happened,” noticing my cock had gone limp. I was embarrassed as I climbed back on the bed, but Sheryl again took the lead, taking hold of my cock as I lay on my back, rubbing it, trying to make me hard.

I had to do something and when she took my cock in her mouth, sucking it, I quickly decided I needed to think about cumming, but it wasn’t working. Sheryl now looked up at me and as she rubbed my cock and fondled my balls trying to make me hard, she asked if it felt good.

I simply nodded my head and said, “Yea.” As she again tried sucking my cock. I realized I had to do something, and quickly decided to start thinking about when John was sucking my cock, and it worked. I become hard as she sucked and rubbed my cock just like John had done.

Sheryl realized how hard I had become and stopping, she quickly grabbed the condom that was laying on the bed. As I watched, she quickly tore opened the package with her teeth, took the condom out of the package, and placed it on the tip of my cock, gradually rolled it down, until it covered my hard cock.

Seeing her body and watching her put the condom on was helping to keep my dick hard and as Sheryl rocked forward to kiss me, she quickly straddled me. She then sat back up, took ahold of my cock, and guided it in her wet little pussy.

I watched her face as she gradually sat back on my cock, bouncing a little, letting it go all the way in. It felt warm and wet and when she started moving up and down, letting my cock move in and out of her, I reached up fondling her boobs with both hands.

I wanted to cum and as I concentrated on cumming, Sheryl lend forward telling me how good it felt as we kissed. As we continued to kiss, I reach back feeling her lower back, eventually feeling her ass as she continued to move up and down. She had a great ass and as we continued to kiss, I found myself trying to help her, wanting to cum.

Sheryl was really wet and occasionally my cock slipped out, but she would quickly put it back in and returned to fucking me, but soon my cock started to go limp; what could I do. Eventually, my cock slipped out and being to soft, she couldn’t get it back in her.

Sheryl asked, “Is everything okay, did it feel good.”

I quickly replied, “Yea, it felt really good, I don’t know,” as I reached between us and tried to put it back in her. It was no use, I wasn’t getting hard. Sheryl rolled of my and tried giving me a handjob, which felt good but I still wasn’t getting hard. I tried to concentrate, wanting to get hard so I could fuck her, and realized I needed to do something.

I started to think about when John had fucked me, and thought about how it felt and it worked. As I got hard, Sheryl took off the condom and continued to rub my cock, eventually taking my cock in her mouth, sucking me. It felt good and I wanted to try fucking her again. I rolled her onto her back, and quickly climbed on top of her, positioning myself between her legs as we kissed and reaching down, I took ahold of my cock wanting to be in her again and when I tried to put it in her, she gasped and said, “Be careful, you don’t have a condom on.”

I stopped but Sheryl quickly leaned up kissing me and said, “Just be careful okay, don’t cum in me.”

We kissed again as I slowly tried to guide my cock in her, and when I was all the way in her again I slowly started to fuck her.

“Oh my god,” I thought, “I want to cum.”

It felt so good and as I fervently fucked her, and as soon as she put her hands on my ass, I could sense she was feeling the same sensation, but at the same time, I think Sheryl was realizing I was close, because she started to tell me not to cum in her.

I was breathing hard, but I always reassured her that I wouldn’t cum in her, and even though I was close, it was always in the back of my mind, not to cum and ever time I stopped to catch my breath, it made Sheryl think I was going to cum, because she would immediately pushed on me saying, “Don’t cum!” All I could think about was not cumming, and I for sure didn’t want to make her pregnant, but I did want to cum. I concentrated and when I was almost ready to cum, I stopped, pulled out, and tried to finish by masturbating to make myself cum.

Sheryl was watching and told me to cum on her stomach. As I looked at her, she fondled her boobs, as I continued to try to cum, but I couldn’t do it and eventually stopped, telling her I was sorry. Sheryl sat up and said, “Is it me,” let me try, as she took hold of my semi hard cock, she had me lay back. It felt good and as I closed my eyes, I again thought about John. I needed to cum for her so she wouldn’t feel disappointed and as soon as she started to suck my cock, I grew hard; I was going to cum.

As I got close, I started bucking my hips, trying to fuck her mouth and when I was going to cum, I lifted her head off and told her I’m going to cum. Sheryl continued to give me a handjob as I concentrated on cumming, thinking about John and suddenly I shot my load on my stomach. Sheryl slowed as she watched me cum, eventually stopping and tasting my cum. It felt good but I didn’t get to cum in her and I had to think about John to make me hard and to get me to cum.

Sheryl wiped to cum off my stomach and we laid there together for a while not talking, just cuddling, until she remarked, “I hope you’re not disappointed.”

I was confused, did she think it was her fault? I quickly said, “No, don’t worry, it was my fault.”

We went back and forth from blaming the condom to her not wanting me to cum in her, eventually agreeing it was neither of our fault, but deep down I knew it was because I couldn’t get my mind off of my experience with John.

I ended up staying the night and in the morning I left. Sheryl suggested we should try to go out again sometime, in which I agreed to do, and we kissed, leaving it open.