How Girls Night Changed My Life Ch. 03

She stopped inspecting me and started to play. Jacking me slowly from the tip to the base. Gently stroking all nine and a half inches of me. Her hands were soft and smooth.

"Can I put your cock in my mouth?" Holly asked.

"Absolutely!" I said.

Holly started with light kisses on the head and then the shaft. She then licked up and down my shaft, covering every part with a thin layer of saliva. Both of Holly's hands wrapped around my shaft and jacked me. Her hand moved up to the tip and back down with small circular motions with each stroke. The tip of my cock was then placed at the entrance of her mouth. Holly's lips parted as she took me into her mouth. Her tongue swirled around the tip as she sucked. Holly took a couple more inches into her mouth and then started to pick up speed. She pumped my shaft quicker and moved my dick in and out of her mouth much faster. No more than a few inches would travel into her mouth and she made no attempt to go deeper. What she lacked in deep throating skills she made up for in enthusiasm. Holly was energetic and gave her all. She would get me close to cumming but never pushed me over the edge. I needed her tight young pussy to get my release.

I untied the two ties holding the bikini top on and then stepped back and made her release my cock.

Holly was surprised by my movement and then said, "This is by far the best cock I have ever seen, touched or suck. I don't know how long I was blowing you. I was so distracted by getting to suck on something so nice."

"You were doing so great Holly. It felt amazing but now I think he needs to explore you little pussy." I said.

The blowjob was good but out of the three people to blow me Holly was at the bottom. I could not wait to get inside her pussy and maybe her ass to.

"That sounds great. Lay down Steve." Holly said.

I lay on the blankets I had put out. Holly stood from the couch. I watched her lower the tiny bikini bottoms to the floor and step out of them. Her bare pussy looked wet and willing. Holly straddled me. Took hold of my cock and lowered herself.

"Let me take it slow Steve. I have never had a dick this big." Holly said.

"Take as much time as you need." I said.

Holly continued down. The tip pushed her lips apart. Holly's pussy was drenched and my shaft slowly entered her canal. About half of me was inside of her pussy when she stopped forcing herself down on my cock.

"Fuck you are big. It feels so good. I have never been stretched this good." Holly said, "Let me fuck you till I get used to you."

Holly raised herself back up to the tip and then back down fucking me. With each motion more of my shaft disappeared into her. After a few minutes of methodical fucking and her getting adjusted to my size I was finally completely inside of her pussy.

"Fuck, you feel so good inside of me. Sorry it took a little while to get your whole dick in me." Holly said.

"I'm not sorry I could watch you fuck me for hours." I said.

"Good! Now that I can handle you, I want you to fuck me good." Holly said as she climbed off my dick and got on her hands and knees. "Fuck me from behind."

I got behind her, grabbed her ass and admired the view for a few moments. Her puckered ass and waiting wet slit looked perfect.

"What are you doing back there?" Holly said.

"I got distracted by how beautiful and sexy you are." I said.

I lined up my cock with her pussy and pushed myself into her. Holly's pussy walls stretched around my shaft as I buried myself to the hilt.

"Please fuck me Steve." Holly said.

No more encouragement was needed. I slid in and out of her pussy at steady pace, much quicker than earlier. Holly could handle the pace. Her love box had accepted my cock and was ready for a good fuck. It was not long before Holly's breathing became much heavier and pussy even wetter. Holly also became much more vocal.

"Fuck Steve. Fuck me. Fuck me harder." Holly said. She continued to let me know her pleasure throughout my fucking.

I could not help but enjoy the view of her ass hole. It had filled my thoughts for the last day and my ultimate goal was to get my dick in her ass. I was concerned that she would be to tight after she struggled with my dick in her pussy and as far as I knew the ass would be tighter than the pussy. That fact was not going to stop me from trying. I placed my thumb onto Holly's hole and rubbed.

"Keep playing with my ass Steve. Push your finger in me." Holly said.

Holly was ready and willing for ass play. I could feel her excitement as I started playing with her ass. I spit on her ass and worked my finger into her ass. My continual fucking sent her into her first orgasm.

"I'm cumming. Keep fucking me. Oh shit. Oh fuck this feels amazing. Fuck!" Holly said.

I never slowed or let her recover. I kept on fucking her and pushing my thumb deeper in her ass. I was surprised to find her ass so inviting. It accepted my thumb with ease. Soon I replaced my thumb with two fingers. With not much effort they slid into her ass entirely. By this point I was getting close to cumming so I took my fingers from her ass and grabbed her by the hips. I pumped in and out of her as fast as I could.

"I am going to cum soon. Where do you want it?" I said.

"Cum in me Steve. I want to feel you shoot deep in my pussy." Holly said.

"Are you sure Holly?" I said with a little concern. I never had to be concerned with my wife or with Kim. Holly on the other hand I did not know her preferred method of birth control and I defiantly did not need a nine-month accident.

She sensed my concern and said, "Don't worry Steve. I am clean and protected so shoot that sperm deep inside me."

I did not have any response. I returned to fucking her hard and fast. Holly reached back and played with her asshole. She pushed two fingers into her ass and fucked herself. Holly pumping her own ass sent me over the edge. I pumped my seed into her. This triggered another orgasm for her. We both finished at the same time and collapsed on the ground.

"By far the best fuck I have ever had. Seriously Steve, that was amazing." Holly said as she rubbed and fingered her pussy. Then licking her fingers clean of our combined cum. "Taste great too."

"That was great but were not done yet." I said.

"You can go again so soon?" Holly asked not knowing my stamina

"Defiantly, we have only begun." I said, "Let me play with your ass a little and let's see if I can fit in there."

"Sounds wonderful. If you can't tell by last night and tonight, I really like anal activities. This might help a little." Holly said as she pulled out a bottle of lube. I don't know where it was hiding but I knew it would help.

"Me too, we really are a good match." I said.

Holly lay with her back towards me. I put so lube onto my fingers and worked them in her crack. I found her hole and immediately pushed my two fingers back in. I finger fucked her for a few minutes and her ass became more accepting. Then I pushed a third finger in. Holly handled everything great, with no discomfort at all, only pleasure. Her ass was stretched and ready for dick. My dick was bigger than any finger combo but was ready to be truly fucked.

"Are you ready to get ass fucked?" I asked.

"I can't wait Steve. I want to feel you big cock in my ass." Holly said.

I spooned Holly with my dick pressed against her ass. I started rubbing my cock back and forth her crack, rubbing the asshole with each pass.

"Stop teasing me Steve. Put him in me." Holly said.

I put some more lube on and then guided the tip of my dick to her willing hole. With little effort the head disappeared. Her ass was much more accepting then Kim's had been. With the lube and her accepting ass my shaft continued to slid inside her.

"Keep pushing. Fuck you feel big but keep going till you're all the way in." Holly said with about half my dick up her ass.

"You want all of it? You want my big dick buried in you ass?" I said.

"Hell yeah! You feel so good Steve. Bury you dick in me and then fuck me hard." Holly said.

I kept pushing as every inch of me was in her ass. She was tight but took me pretty easy. I was in ecstasy with my dick buried in a little college girl's ass. My sex life was reaching new heights and I still had the rest of the night to enjoy her ass. Slowly I pulled almost every inch of me out of her and then slowly pushed back in. I fucked her slow and let my hands roam from her breast to her clit. She was soaking wet.

Holly turned her upper body so her back was flat on the ground and her face turned towards mine. She stared into my eyes as I fucked her and played with her nipples. Her face displayed a look of pleasure and care. More than just a crazy fuck. Almost like she was falling for me. It was a look that you get at the beginning of a relationship where you realize you really like the person. We barely knew each other but her emotions were showing her feelings. I kissed her. The kiss was passionate and loving. More dramatic than any of our previous make outs.

We broke our kiss and I picked up more speed. The whole time she never broke eye contact with me. A few moments later Holly was hit with another orgasm. She moaned and her body tightened in pleasure.

"I can't believe I just came again." Holly said.

"I think I can get you to go a few more times." I said.

"Really!" Holly said.

"Yeah. I think I have it in me as long as you are up for it." I said.

"Of course. Guys my age last a few minutes and it's all about them. I have never been treated so good." Holly said.

"You deserve to be treated good. You want to try another position." I said.

"Yeah that sounds good. I am up for almost anything so whatever you want to do to me, just do it. I trust your judgments and skills." Holly said.

I thought to myself about my skills. A month ago I was a novice, now I have skills. It made me feel good to know I was good at sex. Holly was only my third partner so compared to most people I was a rookie but I had learned a lot in the last month.

I got up from the floor and sat on the couch. Holly straddled my waist and was face to face with me. I directed my cock to her ass. Once the tip found her asshole she started to lower down my shaft. Holly rocked her hips back and forth as my cock slid in and out of her ass. I held her tights as our tongues danced in and out of each other's mouths. Her pace started to quicken and I had to break out embrace to give her more freedom to move. Holly sat up more and I lean back into the couch. She started bouncing with good speed on my dick. To help I moved my hip a little to match her pace. My dick was being pounded in an out of her and our skin slapped with each motion. Holly's hand was now feverously working her clit as she fucked me.

"I am going to cum again. Keep fucking my ass Steve. Fuck me hard." Holly said.

I stopped her bouncing at the top of her motion and held her hips still. Then I fucked her hard. I pumped in and out of her ass as fast as my hips could move. Her orgasm hit and her ass tighten around my cock. I didn't slow but the increased pressure was pushing me over the edge.

"Oh fuck this is to much for me Holly. I am about to cum." I said.

"Shoot it in my ass. Cum in me." Holly said as I let loose in her ass. My cream was shooting deep inside her bowels. I finally stopped fucking her once the orgasm subsided.

"That was amazing. I love your ass." I said as we both caught our breath.

"Thank you. I love your dick in my ass. I have never cum so hard or this many times during sex." Holly said.

"I have only had anal a couple times and you took me so easy. After how tight your pussy was, I thought it would be a lot harder to get in there. I am truly amazed by your ass." I said.

"Well, I do have a reason for that." Holly said.

"Now I am intrigued. Please tell me all about your ass." I said, "That kind of sounds funny to say but I am very interested."

"Ok, I have never really told anyone the story but an man I have only met a couple times seems normal to open up to." Holly said jokingly, "However your dick is still in my ass so it does feel more natural to be open with you about my ass. Its crazy how comfortable I am with you and what we just did has been a total fantasy of mine."

"I'm glad you feel so comfortable. I feel the same way. Everything so far has been so easy between us."

"Now for story but first do you want to lay down and get comfortable first." Holly said

"Yeah that sounds great." I said.

Holly rose off of my lap and my still hard cock slid from her ass. Once off she took hold of my cock and stroked him a few times. Then without saying a word she dropped to her knees and took my dick in her mouth. Cleaning my cock of the excess cum.

After a few minutes of sucking Holly said, "Sorry I got distracted from seeing your cock and how hard you still are. You ready for story time?"

"The blowjob was great but I'm excited to hear where this anal passion comes from." I said.

We cuddled together on the floor and she began to tell me her sex history from the beginning. After getting through losing her virginity and personally experimenting with herself she got to the part I was interested in. The ass.

Holly continued saying, "It was the summer after my senior year of high school. One weekend my parents were out of town and I invited my boyfriend over to my house. One thing led to another and we did what any teenagers would do. We started fooling around. We had sex a couple times before that point so we thought we knew what we were doing. He was defiantly only average in the man department but I was young and he was only the second guy I had been with so I didn't know any different."

"We started fooling around. He went down on me. He was really low and licked my asshole. It was only a quick graze but it made my whole body jump in pleasure. He kept returning to my ass and would linger a little longer each time. I tried to hide my excitement because the idea of being turned on by my asshole was completely foreign. Towards the end his focus was more on my ass and not my pussy."

"Finally I asked what he was doing. He was embarrassed but then told me about anal he had seen in some porn and how he really wanted to try it. Me being naïve and turned on said we could try it. He was super excited that he stopped pleasuring and tried to put it in me. We didn't know what the hell we were doing so with just a little spit he tried to push it in me. To be honest it hurt pretty badly. Before his dick could push into my ass he blew his load. That was it, he was done and I was left unsatisfied with cum in my butt crack."

"We broke up a few days later and never tried it again. I was worried about the pain but the pleasures out weight any negatives. My new obsession was born. I researched everything I could on it from books, to porn or forums online. The porn was great. I realized it was not realistic for someone new to anal. The online forums and books were much more useful. I learned proper cleaning and prep, which is almost a daily thing for me now."

"I learn how I would need to gradually work up to getting a dick in my ass. I started small with my fingers when I would masturbate. Whenever I masturbated and played with my ass I would have my hardest orgasms. I continued to push myself. I moved up to small anal toys. Those were great but I wanted bigger so I increased the size of the toys. Once I was comfortable with those I went to small dildos and would fuck myself. I kept increasing the size until I was comfortable with a large dildo. I was like the girls in porn who could take a dick with little trouble at all."

"Unfortunately opportunities with real dicks did not arise. The first guy I dated in college I asked if he ever thought about anal told me no and thought it was dirty. That relationship ended fast. Towards the end of my freshman year I started dating another guy. After a couple months I asked him if he had ever thought about anal sex. He not only thought about anal but also had experience. I couldn't believe it and asked if he wanted to try it with me. He was ecstatic and so was I. I finally would have a real cock in my ass. With all my preparations I took his six-inch dick easy. I came so hard and from that point I was completely hooked. We did it a few more times before we left for summer. Our relationship didn't last."

"That summer I had anal with one of my high school friends a couple times and that was my last time till now. It's been about a year since I have been fucked in the ass with a real dick so when you licked my ass last night I got so excited. Then you blew my mind tonight, it has been unbelievable." Holly said

"Unbelievable. I am so glad you told me. This has been one of the best nights I have had." I said.

"Of course I pick a married guy to have the best sexual experience of my life with. Will I get to see you again Steve or is this a one time affair for you?" Holly asked.

"I defiantly want to see you again and this has not been an affair. Personally I would like to get to know you better a lot better outside of this store. What do you have in mind for whatever this is we have?"

"I want to get to know you better too but I know we can't have a real relationship with you being married. Now for the question I might regret. What about your wife? We are both guilty in fucking each other but I also don't want to be a home wreaker." Holly said.

"First off neither of us is guilty of anything. We didn't have an affair." I said.

"What do you mean? Your married and we had sex. That is the very definition of an affair." Holly said.

"I don't think it counts as an affair if I have permission from my wife to be here with you." I said.

"Wait! Are you serious your wife knows?" Holly questioned.

"Yes, my wife knows everything I don't keep anything from her. She gave me permission to come here tonight. You actually met her today. You helped her in the store today and she said you were beautiful and very sweet." I said

"That's very nice but so weird. Are you serious about all this?" Holly asked with a concerned face.

"Let me explain. We're a normal couple who have just recently become sexually enlightened. To be completely honest, you are only the third person I have ever been with in my entire life." I said and then went on to tell her the whole story. She became a lot less concerned and more turned on as she returned to cuddle with me towards the end of the story.

"Your story is way better than mine. Your wife does seem really nice, caring and sexy. It caught me off guard to think that a husband and wife conspired some story to fuck me. After hearing everything I don't feel that way at all. This has all been wonderful." Holly said.

"I am glad you are ok with everything. It really is a lot to take in and I hope I didn't scare you off." I said.

"At first maybe, but after hearing you and your wife's experience I am turned on and fascinated by the whole thing. Plus I am going to need to fuck you a lot more." Holly said.

"That sounds great to me. I think you would really like my wife and I think you need to meet her formally. We are having a pool party on Friday and I think you should come. We can get to know each other better and it would be a really relaxed atmosphere for you to meet my wife. It will be a normal pool party, very casual with friend, coworkers and their kids. You could bring a friend to if you would like to be more comfortable."

"That sounds great. I would really like to meet her and hang out with you guys." Holly said.

"Great I am excited." I said

"I know I can tell. You're still hard. Does he need to get in my ass one more time?"

"Fuck yeah." I said.

Holly took my dick in her mouth to get me wet and then turned to spoon me. I lined up my dick with her still wet hole.