A Most Unusual First Time

by Wayne Gibbous

Copyright© 2009 by Wayne Gibbous

Erotica Sex Story: Like any girl, I had daydreamed about my first time. I just never expected it to happen with two male friends of mine who are lovers.

Caution: This Erotica Sex Story contains strong sexual content, including Ma/Fa   Consensual   Romantic   BiSexual   Heterosexual   First   Safe Sex   Oral Sex   .

I was going to be nineteen in three weeks and was still a virgin. Oh, lots of my friends, most, actually, um, really all of them, had given up their virginity long ago. Here I was, a sophomore in college in the fall, vagina never penetrated even by a finger. A guy's finger, that is. My own have been in there lots. But, I know it's just not the same.

Why was I still a virgin?

Well, I really got my figure later, around fifteen to sixteen, even then, I didn't get the big boobs that seem so popular with boys. I'm a nice B-cup but no more.

Also, I just didn't look to get fucked just to tell my friends I'd been done. No, with all the horror stories I'd heard about screaming and pain, blood, all that, I wanted someone gentle, caring, tender. A guy who would stop if I asked him to. How many would do that?

And, I grew up in a pretty small farming town in the Midwest. Secrets just didn't exist and so many guys bragged about every sexual conquest that I didn't want my reputation smeared all over our small town.

It was the summer after my freshman year and I was working in a summer stock company. No, not acting, more along the lines of set and theater production. It was a Monday night, no performance that evening, and I was with my two best friends, two guys, at their apartment drinking some cheap wine that we had.

"I'm ready to lose my virginity," I said, "I'm just not ready to be manhandled or treated too roughly, if you know what I mean. I know too many girls who've had a lot of terrible experiences with all the pain and bleeding and guys just pushing their way inside, that I'm really leery about it."

Now, maybe I'm making a play for these two guys to be the ones but before you assume that, I need to tell you that Steve is bisexual and Brian is gay. They are lovers and live in this apartment together.

They'll be seniors in the coming fall term and I had gotten to know them really well and trusted them completely. The truth is that, yes, I had wondered about Steve, if he might be the one and, yes, I rather liked him in a guy-girl way.

They were both medium height, I was actually as tall as either of them, and they were both gentle and caring guys, I think that's why I trusted them as much as I did. I did have guys at school tossing out the same old, tired pick-up lines that they thought were so fresh and clever, "Is it hot in here or is it just you?" or, well, you get the idea. They made Steve and Brian look pretty good.

So, I was ready. I had begun taking birth control pills last spring and had taken care of my hymen with a few of my favorite dildos back in high school.

I'm not sure exactly how much wine we had had but it was enough that I was feeling pretty good, when I began to understand that these two guys just might the right ones to see me through my quest.

The big problem was that they were lovers. They lived together and slept together. I liked them both as friends and would never do anything to come between them. That, I didn't want.

If this was to happen, I was sure it would be Steve, who, from what he had said in the past, was bisexual though it was back in high school when he had his last girl. Brian, on the other hand, had told me he was only experienced with other guys, never a girl.

So, I decided that maybe we had all had enough wine for me to risk actually proposing that my virginity be done away with that very night, in that very room, in that very bed.

So, while we all lay there on the bed, me between them, I asked, "Brian, would you mind if Steve did the honors of taking my virginity? I mean, I don't want to come between you two. I'd never, ever want that. I want us all to still be friends and I need help getting through this."

"I really don't know what to do but it's okay with me if you want to make love with Steve. Um, I'd like to be with you two if you do it, if that's all right with you?"

"Yeah, that's fine with me," and Steve rolled toward me, got up on his elbow and gently kissed me running his tongue between my lips as he slid his hand up under my sweatshirt and began gently rubbing my stomach. It felt so nice and relaxing, the wine helped, too, of course, and I wanted to move things along a bit not knowing if Steve felt very sure of himself at this point. So, I sat up, reached down and pulled off my sweatshirt and tossed it off the foot of the bed.

As I lay back down, Steve's arm was under me and I could feel Brian's hand caress my butt, then rub along the curve of my waistline. Brian then unhooked my bra in the back and I rolled onto my back and Steve pulled my bra up off me, leaned over and began kissing my breasts.

"Oh, Dottie, you're breasts are wonderful, just perfect," Steve said as he fondled and kissed them.

"You always wear baggy sweatshirts," Brian added. "They are really pretty."

I felt my nipples harden as my breasts were caressed for the first time and I felt pleased that they both liked how they looked. I sat up and pulled off my socks and Brian got up to get us some more wine. Meanwhile, Steve continued to touch and kiss my breasts. It sure had me breathing harder, that's for sure. And, there was a definite tingle going on down inside my panties.

I reached over and took Steve's belt and began to try to pull it open. I had never ever seen a penis before, well, little boy's when I babysat but that hardly counts now, does it? Steve got the picture and stood up and took his shirt, pants, then briefs off.

Well, there it was. A little longer than I expected, a little slimmer than I expected and rather curved upward toward his stomach. Well, well.

I reached over and took it in my hand. My first penis.

As I rubbed it back and forth, I told Steve, "Your's is the first I've ever seen. I'm impressed. This is all new territory for me."

"Oh, wait until you see Brian's, it's bigger than mine," Steve said as he put his hand between my legs and rubbed me through my jeans. It did feel nice but I was definitely ready for more, so I reached down and unbuckled my belt and unzipped the fly and Steve pulled them down off my hips to my calves and pulled my panties down as well. I could feel, as they slid down my legs that they were wet. I was turned on pretty good and was feeling ready for more.

As I kicked them both off, I glanced over at Brian and he started to take his clothes off as well. Steve lay down next to me and began kissing me again, on the mouth, then down my shoulders and my breasts. Oh, did I love him kissing my breasts and sucking my nipples.

Steve's left hand was rubbing on my stomach which felt quite good, then it started moving down across my abdomen to my mound. I closed my eyes and widened my legs and felt his hand caress my pussy. I could tell that I was very wet. No wonder, my heart was thumping, my breathing almost in gasps.

Oh, then, a finger slid inside me. It was really happening. I was really having sex, real sex. And, then, a second finger. Oh, that was so nice.

"Does this hurt at all?" he asked.

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