This is a work of fiction.
(Sorry for the wait guys and gals, had to go out of town for work and just recently been able to get some free time for writing, thanks again for all the e-mails and comments, they do mean a lot and I really do appreciate them, read on and enjoy!)
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Tonight was a good night I thought lying in bed. I had lost my virginity this afternoon and had developed a special relationship with my mother and my sister. One I hoped would last for the rest of my life.
Earlier in mom's bedroom I had found out that Holly, my older sister, the popular girl from school, the one that dated good-looking guys regularly, was in fact a virgin as well.
To be honest I could have gone all night, but when Mom had discovered that about Holly and had, perhaps unthinkingly, blurted it out it made Holly break down into tears.
When that had happened Mom just gathered her close and held her as she cried, she had motioned to me silently to leave and go get to my own bed. I guess she wanted to talk to her; I couldn't help but feel a little guilty as I had left the room, mainly because I felt so damn good. But nevertheless guilt was still there; I was happy and my sister was crying, just didn't feel right.
When I had got back to my room my cock had wilted and tonight's events had slowly started to catch up with me and I took a shower in the bathroom I shared with Holly in between our respective bedrooms. After showering I put on a pair of boxer-briefs and lay down to try to get some sleep.
So here I lay, waiting for sleep to come, even though I knew it would be awhile, replaying all the events of the past 12 hours over and over in my head. Strangely enough even after all the wonderful lustful sex I had had my cock still had life, just thinking of what we had done earlier had caused my cock to stir and stretch out my shorts, tenting up against the fabric.
After a few minutes of staying hard and knowing I wouldn't get any sleep if I didn't relieve the pressure I finally said fuck it and removed my shorts and slowly started stroking it. Closing my eyes I started drifting into my memories of tonight, with a smile on my face I continued stroking.
"Just what do you think you are doing?" I heard my mother ask.
I opened my eyes to see her standing there just as naked as I was looking at me with a small smile on her face.
"Well, um, I was just taking care of myself Mom." Still stroking I wondered why she was in here instead of with my sister, and said as much.
"Well I've been talking with your sister and she wants you to take her virginity, tonight." Saying this she sat down on the edge of the bed and took over stroking my cock, pushing my hand away.
"So son of mine, think you are up to it?" She asked smiling, continuing to stroke me.
"Of course I am, can't you feel it?" I asked laughing.
Mom laughed then too and got up told me to follow her.
I got up and followed mom from the room, my eyes locked on that beautiful ass as it sauntered through the doorway and into the hall.
When we entered Mom's room Holly was sitting there on the bed with her head down, she looked up as we entered.
Her eyes were still a little puffy and looked like she had been crying but she smiled at us as we entered and came over to me and put her arms around my neck and snuggled her head into my shoulder.
I just held her for a minute while Mom walked over to the bed and sat on the edge.
"I'm sorry Bobby; I hope I haven't ruined our night." Holly mumbled, still hugging me.
"No sis you haven't, we were only worried about you, not ourselves." Slowly I started stroking her hair, running my hand from the top of her head down to the base of her neck, comforting her.
After a minute of this Holly pulled back and looked into my eyes and said.
"Bobby, will you make me a woman tonight?"
I smiled and replied "Of course."
Hearing that Holly grinned and took my hand and led me over to the edge of the bed. Letting go she crawled up on the bed and still on her hands and knees looked over at her shoulder at me and winked.
"Mom, do you think you can get me ready for Bobby?" She asked, looking over at our mother.
"Of course sweetie, I'll make sure you are good and wet for him." Mom replied standing and walking over in front of me and crawling onto the bed behind Holly. Holly still on her knees shook her ass playfully at her mother as her mother's lips closed over her pussy and gently started nibbling and tonguing her pussy lips.
Holly looked back at me again and gave me a 'what are you doing stare?' Unconsciously I had begun to stroke my cock as my mother had started the fine art of cunnilingus on my sister, making it next to impossible not to become aroused at the sight.
Holly then kind of glanced over at our mother and back me again quickly and I got the idea.
Moving closer to Mom I asked "Mom, do you mind if I warm up a bit for Holly?"
Our mother knew exactly what I meant, she had been kind of half-laying on her side twisting up to eat Holly but now she moved onto her knees and spread her legs slightly in answer to my question.
Seeing the invitation I moved in behind Mom and rubbed my cock up and down her labia and found her to be slightly dry. Using a little bit of spit I polished the head of cock with it and started rubbing it up and down through Mom's outer pussy to see if I could get her juices flowing. Apparently I was doing a good job, after a minute she had started to leak noticeably, either that or the fact she was eating her daughter out and getting ready to fuck her son again was turning her on.
With Mom good and wet now I gave the head of my cock one last rub through her folds and then slowly pushed in causing Mom to moan as I entered. With this just being a warm up I knew I didn't want to cum in Mom, not this time, I was saving that for Holly, so I took my time, long and slow strokes in and out of her pussy.
Looking down, seeing Mom's pussy lips slowly coming slightly out with me when my cock withdrew was such a turn on, it was taking every ounce of my self control not to turn into a rutting beast and ravage this wiling female below me.
"Alright Bobby." Mom said suddenly, breaking the spell I was under, I had become almost hypnotized watching my cock slide in and out of my mother.
I glanced up and saw Holly looking back at me grinning and Mom looking over her shoulder at me doing the same.
I just smiled and gave Mom one last quick thrust that made her jump a bit and slowly withdrew. As the last inch came out and the head of my cock popped out into the open I couldn't help but give a sigh of regret. Mom's heat and pressure where something I never wanted to be without, but I knew I wouldn't be left hanging for long. As soon as I pulled all the way out Mom moved over on the bed and made room for me as I climbed up and got close to my sister's very wet and very excited looking pussy.
"Ok Bobby, Holly is ready for you, but listen to what I say, do not go slow, it's better to have quick pain than letting the pain build by slowly doing it, understand?" Mom asked me looking at me seriously.
I nodded in understanding looking at my sister who had her head down and her hands gripping the sheets in front of her like she was going to strangle them.
Mom then reached over and placed my cock at my sister's opening and let go.
I looked down, and suddenly I didn't want to do it, I just knew it was gonna hurt my sister and I didn't want to cause her any pain.
Looking over at Mom she seemed to understand what was going through my head.
"Bobby, this is natural, women go through this, and its better this way than in the back seat of a car or in a cheap motel with some loser that says he loves you just so he came take your cherry and cum ten seconds later. Trust your mother in this Bobby." She said, rubbing my back, lightly scraping it with her nails.
"Bobby, listen to Mom, I know it will hurt, but I also know you really do love me, so please, help me ..." Holly said, still not looking back.
Still a little unsure about it I just decided to trust the resident female expert on vaginal penetration, our Mom, and slowly started to inch inside my sister's tight sheath.
And man was she tight, Mom was tight as well but not like this, this was like a too small pair of gloves for my hands. I made progress, but slow, slowly I could feel her vaginal walls stretching to accommodate me, I knew I could go in harder but the less pain I caused Holly the better.