Diane Part Five, Debra Part One  

rm_harshawj 52M
761 posts
10/4/2005 11:29 pm

Last Read:
3/5/2006 9:27 pm

Diane Part Five, Debra Part One

[This is by far the longest post I have ever written. There is a lot of meaning in it for me because aside from the fact that it is a “Diane Story”, it is also a turning point in my life, though I would not know that for almost a year afterwards. It is presented here as a piece of erotica, but it is my life and as true to the actual events as I can remember.]

This will be the last story I relate where Diane figures prominently. There are other stories, but for sheer erotic content, this still ranks up there. I could relate other more prosaic acts of exhibitionism and public sex, but they would not compare to the first three I have related. So rather than bore you, I will lay out one last Diane story and be done with her (maybe).

I pick up this story directly where I left off in Diane Part Three:

I stealthily removed myself from her, adjusted and zipped. Diane finally got up and excused her self for the women rest room, me looking none the worse for wear except for the cum drenched briefs, conveniently stowed in my pants. I just sat there for a while.

Later, Debra sat down beside me, put her arms around me and said, “Dog. What are you two doing later?” And that was a night and another story.

After The Dance:

Well what was I going to say, “Well, I plan on have wild sex all night with Diane.” It would have been the truth, but why rub it in. I had not hooked up with Debra before, so it was not as if I was at liberty to have her join us, but was that what she had in mind?

“Not sure really, kinda left the evening open, you know…”

She put her hand on my cock and said, “Well let me know” and walked away to get something to drink.

Ok, now that was a pretty clear message, she wanted to fuck me and she wanted Diane there too. So when Diane came over I asked her if she wanted to have some company for with us for the evening? I knew the answer, but she wanted to know it if was another guy or a girl. I told her about Debra and she said “Even better!”

Now Diane was good looking I have mentioned that, but Debra was 5’4”, slim in all the right places and stacked with healthy 38DD’s. She has incredible brunette hair and the sweetest face you could ask for. In truth, I was very attracted to Debra but I did not know the extent of that attraction at the time. For now it was just an animal attraction, yeah, I wanted to fuck her too.

A few more songs later Debra joined Diane and I for a few “group dances” and the dance finally ended, but not before Diane and Debra got together and had a little talk. Do I know what was said? Nope, and I do not care, but it turned out that we were giving Debra a ride home.

Now Debra had a couple of secrets that she did not share with us at the time. The first was she had skipped 11th and 12th grade in high school and was all of sixteen years of age. The second secret we found out later.

We got into my car, Diane made sure she was in the back and let Debra ride up front with me. Seems Diane had some plans for Debra and they became clear as we started driving back to my place. Diane wrapped her arm around Debra’s neck from behind and started caressing her from the back seat. She worked her way down Debra’s blouse and before long she was fondling Debra’s breasts. Debra seemed very nervous at first as Diane’s slender fingers found their way under her bra and started playing with her nipples. But a few words from the worldly Diane seemed to ease her enough for her to relax.

So here I am, driving home and my girlfriend is fondling another woman, and I could not participate. Not fair, not fair at all, so I found a dark street and pulled over.

Debra, oblivious to everything other than Diane’s hand finally realized we had pulled over as my hands explored her lush hair and I was leaning over to kiss her and her nape… She loosened her blouse a little and pulled my head down to her breasts to lick them and nibble. She was writhing in pleasure very shortly, Diane acting as conductor, directing the action.

Debra got her wits back a bit and started to fumble with my belt. It seemed she had no idea how to release my pent up manhood, and Diane put a stop to things immediately. I would have helped the action, but Diane stopped that too. Seems Diane had something on her mind and suddenly they were out of the car leaving me behind. When I got out to join them Diane shoved me back in the car with a “Down Boy” and so there I sat.

A few minutes later the two were back in the car, Diane in the front this time and Debra riding in the back seat. All I got was a “OK, just get us home, do it quick…” and so I did. I may have even blown a few red lights but it was all good, “Cop didn’t see it, I didn’t do it” was my driving motto in those days. We got home in record time.

Up to the apartment we went and Debra was immediately on the phone, I could here her making an excuse to her mother about staying at a girlfriends house and she would be home in the morning. Meanwhile Diane grabbed me and took me into the bedroom. There she threw a robe and some shorts at me. She told me to put these on and leave the two of them alone until she called me and pushed me back out into the living room. Debra was just getting off the phone and Diane immediately pulled the two of them into the bedroom.

So there I sat, me with raging hormones and two hot women in the bedroom and I was not allowed to participate. I couldn’t hear any action happening, so just sat down on the couch and waited. I didn’t have to wait long, fortunately.

Diane came out in a shear camisole of peach, a very pretty thing I had bought her a few months back as a special treat. She looked so good I wanted to do her right there and then. She put her arms around me, brought her lips to my ear and said, “If you laugh or giggle or anything wrong, I will kill you.”

I backed away, what the hell was going on? “You’ll see … I have a feeling it is going to be a night of firsts.”

Oh my god, then it dawned on me. Debra was still a virgin.

“You just do as I say, I know you will like it, but just be cool” was the last warning I got as Diane ushered me gently into the bed chamber.

The room was lit in candle light, the bed was covered in a sheet that Diane and I used for food play, and Debra was sitting on the end of the bed in one of Diane’s frilly white wraps. It was not big enough for her (up top) but it did not matter as I had a feeling it would not stay on long.

Diane brought the three of us together at the end of the bed and she started to kiss me. I followed suit and kissed her back. I ran my hands through Diane’s hair and she pulled Debra into the act. I started kissing both of them, running my hand though their hair, kissing necks in turn, licking ears and tongue play. After a lot of this Diane pulled us down to the bed and we both explored Debra’s bountiful tits. I licked them and sucked on them gently playing with the nipples and the sides, Diane’s and my lips occasionally meeting over a breast and kissed with Debra’s hard nipple in between.

Eventually Diane turned the exploration over to Debra and she explored Diane’s firm bosoms and then my chest. Eventually the two put me in the middle and they started to explore my body, slowly and methodically. First one then the other kissing my chest and nipples, kissing up and down my neck, running their hands over my body. It was agonizingly hot, I so wanted to fuck them both. I so wanted to be in them.

Then Diane did something I did not expect at this point. We had this thing, if she wanted me to go down on her she would flick my ear till I got the clue. She flicked my ear.

I slowly started moving down her body, taking time to suck on her tits nice and hard, getting her all excited, I moved a hand down to her pussy and began massaging her clit. Oh, she was so turned on, it was incredible. I continued with light kisses down her tummy and her pubes. Finally I repositioned and allowed my tongue to caress her swollen clit.

My hands worked Diane’s tits as I plied deep kisses to her labia, tongue darting in and out ever so quickly and lightly. I could feel and taste her orgasm as I did it, I know she loved this. I picked up the tempo and Diane pushed my head harder into her slit, forcing me to tongue her deeper. She was really going.

Debra picked up my hand and put it to her breasts inviting me to entice her more, and I did. I could feel her trembling under my touch, this girl who had never been touched like this. She moved my hand down her body.

Diane noticed the progress and had me pay the same attention to Debra as I had to her, so again, I repositioned and began kissing Debra, first on the lips and neck then slowly down to excited nipples. I think she had an orgasm right there, but I was not sure at the time. I continued down to her secret garden and heard Diane telling her to relax and just enjoy it. She told her if she did not like something, just pat me on my head and say no. I tongued her belly button on the way down and she shuttered again. I repeated that little action since she liked it so much and she relaxed into it.

Eventually she pushed me down to her pussy. Her hair there was incredibly fine and felt nice on my face. I applied tongue to clit and she nearly jumped up. Diane held her back and I continued. She squirmed under my application but did not stop it. She pushed my down further and I darted my tongue in, but not too deep, I could not go too deep after all, there was an intact hymen there. I had never encountered this so played it for what is was, something new and interesting. I licked it, I rimmed it and poked the tip of my tongue past it a bit and she came in gushes. It had never occurred to me that a virgin would cum that hard and caught me by surprise. I lapped it up and she just kept cumming.

Diane pulled me off her and we all rested for a while regaining our composure, me on one side and Diane on the other, worshipping Debra’s virgin body.

I was still horny as hell even though they had gotten off well, but I could wait. Then I felt it. A hand sliding into my shorts. Diane smiled and the two of them pulled the garment off me slowly and then they moved down to my cock. I guess it was show and tell time as hands moved over my manhood, at first just touching it, then down to my balls. Diane did this thing with her finger tips, lightly stroking up from my balls all the way to the tip is my cock. I always loved that. Debra tried it too. A little rough, but good all the same and the two giggled.

“Go ahead, taste it. It’s good. Like this” and I felt the tip of Diane’s tongue on the head of my prick, lapping up a little of the fluid that the two had evoke from me. Diane smacked her lips… “Umm, try it” and I felt another tongue slowly take what Diane had left her. “Not bad?” Debra agreed, it was not bad, and wanted to see if she could make me produce more. Diane assured her there was plenty more where that came from (ha ha) and slowly took me into her mouth.

I have said it before, and I will say it again, I do not know where Diane learned her oral technique from, but she was good, and now she was teaching Debra. I guess I was just there willing guinea pig.

Debra tried the same thing on me only with a little too much tooth. Diane warned her of being too rough, after all, would she have like teeth on her clit? Debra got the picture and did better. Diane taught her to use her tongue with it too, the lips play the pussy and the tongue springs a dynamic surprise that a vagina can never match. Oh it was so good.

They moved to kissing and licking my shaft and balls and I had to stop them several times. Diane told me not to cum till she wanted me to, so I had to be sure not to crest the ridge of climax. I would pat them on the head as I got close and they diligently stopped, sometimes just examining my member.

Diane saw that I was just about there, to the point that I could not hold back even a moment and she told Debra I was ready to explode because they had done such a good job. She wanted Debra to watch as I ejaculated for them. Debra had never seen a man cum before so Diane performed the final blow.

I came like a god damned fountain all over Debra’s and Diane’s faces. Diane bent over and sucked me and then let Debra do the same as the last of it flowed into Debra’s mouth. Diane bent over and licked up the spew from Debra’s face and Debra did likewise, enjoy the new flavor she had discovered. Finally the two soul kissed and shared the bounty.

Diane assured Debra that I was a horn dog and that the evening was not over just because I had come once (well twice but the first time was hours ago at the dance) and that there were still matters to be attended to. But we all took a break and had a drink and cuddled for a bit.

She was right, the evening was not over, but they wanted action a bit sooner than I was ready for, so Diane suggested Debra practice giving head on my flagging member. So Debra bent over and took my whole cock into her mouth and sucked on it as Diane instructed. Seeing as I was still only semi, Diane figured I needs some encouragement and straddled my face giving me full access to her cunt. That did the trick. I became erect while still in Debra’s mouth and she loved it, gobbling on it like a greedy little slut, becoming more and more enthusiastic as it grew.

Diane finally put a stop to Debra’s practice, both of us kissing her as we laid back on the bed. Diane positioned herself in the middle and pulled me on top of her. It was time to finally fuck my girlfriend in front of an attentive audience. Diane told Debra that some guys need a little help with entry and showed her how to position a man for better access and I slowly slide home into Diane. Debra watched and played with herself as Diane came several times, god I loved feeling Diane’s cunt squeeze me in orgasmic bliss.

“Your turn” and Diane rolled out of the way and Debra was placed squarely in the middle. “Don’t worry about positioning, he knows where it’s at. And you, veeeeerrry slow. So slow it hurts, you got it?” I got it. “Beside, I know you, you like it tight. You wouldn’t want her to be loose for the rest of her life would you?” I had to agree, who would want a loose pussy. “Then take it real slow.”

She explained to Debra that it may hurt a bit but that was okay. Concentrate on the good feelings and enjoy the pain if she could. Debra relaxed and I mounted her slowly. First just the tip of my prick slowly massaging her labia, then putting a bit of pressure on her hymen. At first I could only get the tip in a little bit, but after about five minutes I was able to get a little more in. Diane slowed me down even more, it would not do to rush her defloration. Slowly, oh so slowly, I got the head of my cock in and started to work ever so gently into her. As I got half way Diane started to encourage me to speed up the pace and I did. With a stronger thrust I was in, all the way in and a look of pain crossed Debra’s face. Diane stopped me as I was shaft deep and we held it there.

Debra relaxed and again I stroked my rod slowly in and out of this virgin pussy. Like Diane, Debra was very tight and it was oh so sweet. I could not help it, I started to pick up the pace and Debra pulled my hips even closer. Diane propped a pillow up under her and I fucked Debra even deeper. Debra’s cunt tighten and grabbed me like a vise and then tried to push me out, Diane told me to go deep and hold it there as Debra had her first vaginal orgasm.

As this orgasm faded I took up the beat again, this time concentrating on depth and short hard strokes. I could feel the back of Debra’s vagina on the end of my cock, tickling her deep and again I could feel the waves of pleasure coming over Debra. I worked it harder, I was getting close to exploding and Diane knew it. She started talking dirty and Debra picked it up, Debra was loving this. I rammed it deep and Debra shock in massive waves of sex and cum and I did likewise, over and over and over again.

Diane would not let me pull out until I was flaccid, either she wanted me to savor the virgin I had just inducted into womanhood, or she knew something I didn’t. Either way I stayed in Debra’s secret treasure for a good ten minutes as we both calmed down and relaxed.

When I finally did withdraw the sheet was soaked in cum, and to my surprise very little virgin blood. Diane produced a tampon and inserted it gently into Debra, telling her to change it a few times over the next couple of days, but no sex for at least a week. Where did she come up with this? It didn’t matter, we were all exhausted and I fell asleep with two women, one on each shoulder.

Later the next morning I made love to Diane again and Debra participated in every way but sex. It was a glorious night and day.

The next week Debra came back for more and it was wonderful. Little did I know at the time I had deflowered my future wife.

Become a member to create a blog