The Benefit of Friends

Suddenly I was thrown for a loop. Dana popped her head around the corner from the kitchen and asked if I wanted anything to drink.

"No, I'm good" I answered. I was very confused at this point. Obviously this was not about sex, but if it was not, then why was I there, and why in the world was Dana there?

Dana was the final member of Natalie's close group of friends. I did not know her that well because she and Natalie did not hang out together very much. I was some told long ago that while they were friends, Natalie and Dana did not get along very well. Rachel and Dana, on the other hand, were the best of friends. They worked together and were very close. While she was not an unattractive girl, Dana was the least sexually appealing of Natalie's friends. She was around 5'5" tall. She was not as plump as Allison, but she did have wide hips and gentle curves. She had brown hair that came to her shoulders. From what I could tell from looking at her though her always modest clothing she had smaller, but still nicely shaped breasts. All in all she was not the most attractive of girls, but was not at all ugly.

She was currently planning her wedding to a guy named Cody. I had met him a couple times, but was not impressed. He seemed to be a socially backward man. He was also not very intelligent. He was very nice though, and he seemed to make Dana happy, so who was I to judge? The wedding was supposed to take place in a few short months. Natalie and I had been invited to attend.

Dana came in from the kitchen with two glasses of lemonade. She handed one to Rachel in her chair and took a seat on the far end of the couch I was sitting on. The girls sipped their drinks, and nothing was said.

Finally I the curiosity was too much for me. "What is going on guys?" I asked.

The girls laughed to each other. There was obviously something I was missing. "Ok," Rachel started, "I've got something to tell you."

"Okay..." I said.

"I'm pregnant!" Rachel said, very excitedly.

"That's great!" I said. I was happy for her. "Congratulations" I added.

"Thank you" Rachel said.

"You're welcome" I replied.

"No, thank you" Rachel said again, emphasizing the 'you'.

"Umm, for what?" I asked. I knew exactly what she meant, but as I glanced toward Dana I wondered why she would be so forthcoming about it with her around.

"You know exactly what for," Rachel said, "and so does Dana, so it's ok. Don't worry about it."

"You... you told her?" I asked, swallowing hard and wishing I would have accepted the offer for a beverage.

"Of course she did" Dana said. "Besides, I knew Sam couldn't do it, so I knew it had to be someone else."

"Oh," I said to Rachel, still concerned, "well I am still happy for you and for Sam. I am glad that I could help."

"Well, if you are up for it, we have one more thing that you could help with" Rachel said.

What did she want now, I thought. She's already pregnant. And what in world was Dana doing here?

"Ook...." I said.

"Well, it's actually me that needs help" Dana said.

I just looked back and forth from Dana to Rachel. One of the two of them had better start making sense soon, I thought.

Rachel said, "You know Dana and Cody are getting married in a few months, right?"

"Yes" I said.

"Well, before her wedding, there are a few things Dana wants to do" Rachel continued.

I suddenly realized where this might be going, and I honestly was getting a little excited. "And that would be...?" I asked.

I guessed Dana must have been very nervous about all of this, because Rachel was doing all of the talking, but at this point Dana suddenly blurted out "He won't touch my butt!"

We all laughed. I was really not expecting that, or any of this for that matter.

"Right," Rachel said, "one of the things she would like to try before the wedding is anal sex. From what she has told me, Cody refuses to do anything back there, and since you were so willing to help me we thought maybe you would be willing to help her out too."

I was shocked. I could not believe this was happening. At the same time, though, I was incredibly turned on. I had always been interested in trying anal sex, but none of the girls I had been with were willing to try it. "I think I may be able to help you with that problem" I said.

"Good!" Dana said, obviously excited.

"I have just one question," I continued.

"What?" Dana asked. She seemed nervous again. Perhaps she was afraid I was not actually going to do it.

"Not that I mind," I said, "but if that's what you want, why is Rachel here?"

Rachel answered my question by standing up and walking toward Dana. "Well, the reason I am here," she said, "is to help Dana with the other thing she wants to do before she gets married." With that, she was now in front of Dana. She took Dana's hands and pulled her to her feet. The two girls looked into each other's eyes and they began to kiss.

My jaw fell open. As I watched Dana and Rachel were making out. Rachel wrapped her arms around Dana's waist, and Dana rubbed her hands up and down Rachel's upper arms and then to her chest. I started thinking that Dana had obviously been as interested in Rachel's breasts as I had been.

Suddenly I realized what was going on. I was brought her to join in, not just watch. I got up from the couch and walked over to where Rachel and Dana stood kissing. I stood beside them, my hands roaming over their backs and their butts, squeezing both. Rachel had a firm, tight butt, whereas Dana's was fuller and softer. I could not believe that soon I would be playing with it, doing things I had wanted to do for a long long time.

The girls broke their kiss. Rachel leaned toward me, and we kissed. We made out for a few moments, and then I turned to Dana. I leaned in and she and I shared our first kiss. Dana was a shy kisser, not seeming to want to open her mouth to me. I knew that is probably seemed odd to her to be doing this with someone other than her fiancé, but I pressed on, wiggling my tongue into her mouth. If we were going to eventually have anal sex, she needed to get comfortable with doing things with me right away. Soon her and I were making out like teenagers.

Dana and I kissed for much longer than Rachel and I had, but we finally broke our kiss. During the time that Dana and I kissed, her hands never left Rachel's breasts. Rachel seemed to notice Dana's interest in them and pulled her shirt over her head. She wore a leopard print bra that was very sexy, but neither Dana nor I wanted to look at it. I moved my hand up and unhooked the bra, and Dana pulled it off. After Rachel was topless she and I helped Dana take her shirt and bra off. Dana never seemed to dress very flatteringly when I had seen her before so I never really realized how nice her breasts looked. They were not as big or beautiful as Rachel's, but they were very nice.

The three of us began to make our way into Rachel's bedroom. By the time we got into the room the three of us were all topless and Dana had removed Rachel's pants. Once in the room Rachel lied back on top of the bed. Dana climbed on the bed next to her and began kissing her. They only kissed for a few moments before her kissing traveled down Rachel's neck, then her shoulder, and finally to her right breast. Dana began to kiss and suck on Rachel's nipple. I got onto the bed on the other side of Rachel and began doing the same to her left breast.

Dana seemed timid about what to do with Rachel, but I wasted no time in letting my hands roam over her body. My hand found her thigh and lightly pulled her legs apart. I began to lightly run my fingers over the crotch of her panties, feeling the damp line underneath.

Dana noticed what I was doing, and obviously wanted Rachel's pussy all to herself for now. She stopped tasting Rachel's breast and moved down between her legs. I pulled my hand back, allowing her access and she pulled Rachel's underwear off of her. Dana started touching Rachel's legs and thighs. As Rachel and I watched Dana started to touch Rachel's pussy. Her fingers lightly ran up and down her lips, and then slowly went inside. Then Dana leaned down and began to kiss and lick Rachel's vagina. Rachel began to moan. I knew Dana had never done this before, but she obviously thought about doing it enough times to know exactly what to do. As Dana continued to pleasure Rachel's pussy I returned to her breasts. While she continued to orally attack Rachel, Dana undid my pants and pulled my member out. She gently stroked it while she ate Rachel's pussy. Soon Rachel was cumming from the double team of stimulation Dana and I were giving her.

After Rachel had orgasmed a couple of times she told Dana it was now her turn. Dana rolled onto her back and Rachel went right to work giving her the same oral pleasure she had been receiving. Dana began to thrash about on the bed as Rachel licked. I wondered if this was Rachel's first time with a girl, but I had more important things to do than wonder about that for too long. As Dana moved about I noticed that she continued to pick her back side up off the surface of the bed. Every time she did so I got a nice view of her butt, my target for the day's activity.

I decided it was time for me to begin playing. I had Rachel get up from between Dana's legs and I replaced her. I began by licking Dana's wet pussy lips. I licked her clit and tongued her hole for a few moments before my tongue began to head south. I flicked my tongue along the small patch of skin that separated Dana's two holes, but quickly found her back one. As my tongue made contact with Dana's tight little butt hole she began to lift her legs up. Rachel moved around beside Dana facing me and helped Dana pull her legs up. My tongue went back to work on Dana's butt. I stated lightly flicking the tip of my tongue around her hole, and then slowly began to push it inside.

Dana was moaning very loudly as my tongue slowly entered her backside. I pushed it into her and pulled it out again several times. The taste of it was different, but not bad. The idea of doing this to her, and knowing what was to come next were extremely exciting to me. After I had made love to Dana's butt for several moments with my tongue and she was very wet with my saliva I pulled my tongue out and replaced it with my finger. As I was doing this, Rachel was using her fingers to pleasure Dana's vagina.

I looked up into Dana's eyes as she looked at me as I slowly slid my finger into her butt. She was incredibly tight, but my saliva had made her slick enough that I was able to slide my finger up to the second knuckle. As I began to move it in and out Dana was moaning uncontrollably. I knew that if I was going to eventually get my thick penis into Dana I would need to stretch her out more, so I slowly slid a second of my fingers into her. This added pressure on Dana's backside sent her over the edge. She panted and groaned and yelped as she had a massive orgasm.

As I pulled my fingers out and Dana calmed down Rachel turned to Dana and asked "Are you ready?"

"Yes," Dana replied.

Rachel got into her bedside table and pulled out a tube of lubricant. She took some and squirted it into her hand and then rubbed it on my rock hard member, getting it nice and slick. She then squirted some onto Dana's backside. She used her fingers to rub it all over her hole and then pushed her fingers inside to get it ready too. It was amazingly sexy watching Rachel finger Dana's butt.

This sexy sight did not last long though. As soon as Dana was properly lubricated Rachel got out of the way to allow me access to Dana. I moved close to Dana and lined my penis up with her hole. I placed the tip on her hole and looked into her eyes as I pushed in. It was still very tight, and I had to put a great deal of pressure in order to get myself into her. I slid about a quarter of my shaft into Dana's butt. Dana had a look of obvious pain on her face the entire time.

At this point I stopped and asked Dana if she was ok and wanted me to continue.

"NO... I mean YES," Dana said between moans and pants. "Please don't stop," she added.

I pulled my penis almost all the way out and then pushed more of myself back into her. I did this again and again, very slowly, but pushing more in each time.

"This feels sooo good!" Rachel said. With that I knew she was ready. I began picking up the pace. Soon I had a good rhythm as I fucked Dana's butt with the full length of my shaft. She was moaning and screaming like I had never heard before. She had at least three orgasms before I felt my own building. I gave her one last, powerful thrust as I exploded deep in her backside.

I pulled myself out of Dana, both of us out of breath. I looked at Dana's bottom and noticed some of my semen that I had just squirted into her was beginning to leak out. Rachel noticed it too and quickly leaned down to lick it up. I knew after my time with Rachel, when she did not want to 'waste' any of my cum, that she enjoyed the taste of it, but it did surprise me just how much she really did enjoy it.

After Rachel was finished cleaning Dana's bottom Dana was wore out. She lied on the bed breathing heavy, looking happy and satisfied. I knew, though, that Rachel was not yet satisfied. Once Rachel was done cleaning Dana she turned her attention to cleaning my member. After she licked me clean, she continued to lick and then started to suck on me. I had forgotten just how amazing it felt when Rachel did that. Although I had just had one of the greatest sexual experiences of my life my having anal sex with Dana, Rachel's skillful mouth had me growing hard again in no time.

Rachel then rolled onto her back. I knew what she wanted. I got between her legs and immediately began making love to her. I went slowly at first, but Rachel began panting and begging me to go faster. Soon I was pounding into her hard and fast.

"Cum in my mouth" Rachel told me. I was still surprised how much Rachel enjoyed the taste, but her wish was my command. When I knew I was close to orgasming I pulled myself out and moved up close to Rachel's head.

"I want some too" Dana said, moving for the first time since I had cum into her butt, she got close to Rachel. The two girls used their hands to help me finish and I started to cum. I did my best to shoot some into each of their mouths, but I missed some, splashing it on their cheeks and chins. They looked at each other as I collapsed into the bed and laughed, and then leaned in and licked my cum off each other before kissing passionately. I watched as the girls made out realizing I had just had one of the greatest sexual experience I would ever have.

After some time the three of us finally got dressed and I went to leave. I kissed each of the girls, telling them that if they ever needed anything again to call me and I would be right over. We all laughed as I left.

Epilogue: Judy

I sat at home one night. It was late and Natalie was out. I assumed she would not be home that night. I was almost positive she was with a guy. It was getting late, and I considered heading to bed. My mind began to wonder. I thought about what I had been through over the last couple of months. I had ended up having sex with each of my girlfriend's circle of friends. Never would I have imagined that would ever come to pass, but I had enjoyed it very much and hoped I could do it again with some of them soon. I also wondered who else I might be able to have some fun with.

I was about to head for bed when I received a phone call. It was from Judy, Natalie's mother. She told me that Ben, her husband and Natalie's father was out of town and the power in her house had suddenly gone out. She asked if I would be able to come over and see what had happened. Since there was no storm or weather to cause the power outage, I assumed she had possibly blown a fuse. I agreed to go over to see what I could do.

I arrived at Judy's house quickly and noticed from outside that there were indeed no lights on in the house. I went to the door and let myself in as I always did. As I entered the house I noticed that there were several candles lit and burning throughout the house.

I called for Judy, not seeing her anywhere.

"In here" she called from the next room. I looked toward the doorway as Judy came into view. As I looked on Judy came into the room wearing very revealing lingerie.

My jaw dropped. I had always thought Judy was attractive for a woman of her age, but I had never realized just how sexy she looked or how amazing her body was.

"Maybe you can help me with something else first" she said to me.

I realized that my sexual adventures were just getting started.

THE END