A First Time for Everything

During my time in college I attended a commuter university in my home city, so I still lived at home until I went to work full-time. I had a very active social life at the time since most of old high school friends and my new college friends were almost always around.

My bedroom was small and full of my stuff, as it was the only space of my own that I had. Almost half of that space was my waterbed. So when company was over, which was often, somebody sat on the bed and somebody sat on the one chair. One day my friends Deanna and Jenna had dropped by to visit. Deanna was a rail-thin brunette and Jenna was a 'plump' red-head.

Deanna was an old friend from high school who lived in my neighborhood. We had ridden the bus home together for quite some time. Jenna was a newer friend from college who had recently begun dating another of my old high school friends, who she had met through me. I had never so much as kissed either of them. We'd never even flirted. We were all unquestionably "just friends."

I was sitting on a chair with my legs up on the bed. Deanna and Jenna were both sitting on the bed. As we sat and talked Deanna made herself more comfortable by innocently putting her feet on my lap. A few minutes later she shifted her foot and accidentally rubbed my crotch with it.

"Sorry." she said.

Jokingly, I said "Don't appologize. You can do that anytime you want." She got a coy little smile and left her foot where it was. We went back to our previous conversation, and slowly she started massaging me with her foot.

We kept talking and she kept rubbing me through my jeans, as if nothing was going on. She was making a game out of if to see if she could get me to stutter or forget what I was talking about, and doing a good job of it. She and Jenna were both getting a big kick out of this.

After a few minutes her foot got more brazen and I stopped trying to pretend I was having a conversation. I laid my head back on the chair and moaned.

"Ooh that's good..." I said.

She said "So you like my footjobs?"

"I'll say he does!" Jenna said, starring at the bulge I was making against my black jeans. "Do you think you can make him cum doing that?"

"Let's find out." Deanna replied.

She rubbed my cock with her feet for a long time, hoping to make me cum in my jeans, but I was nowhere near it. Suddenly, she sat up and put her hand on my bulge, gripping it hard and massaging it with her fingers.

"Oh, goddd..." I moaned.

Jenna sat forward and lifted my shirt over my head. Deanna ran her other hand up my chest lightly. Before long both of them where licking my chest, sucking my nipples, and teasing me with their hands. Then Deanna turned her attention back to my cock.

Jenna said "I think I had better just sit back and watch now. I have a boyfriend."

"Arumph..." I said. I'm not even sure what I meant, but I doubt it was anything particularly deep.

Deanna said "Are you going to cum soon?"

I said "The truth is, I've never cum from a handjob, not even my own. I always have to resort to... other means."

Deanna grinned like a cat with a cannary. She turned to Jenna and said "That sounds like a challenge."

"Go for it." Jenna laughed.

"I'll just keep rubbing you through your jeans," Deanna said "because I have a boyfriend too."

"You can do whatever you want." I replied. Then she told me to lay down on the bed. I got up to move and my cock nearly broke through my jeans it was straining so hard against the black denim.

"You really are enjoying this!" Deanna said.

"Well what did you expect?" I answered. She gave me that coy smile of hers again.

With me on my back she attacked my cock with renewed fervor. She rubbed it gently for awhile, then hard and slow, then hard and quick. I moaned and bucked in pleasure but was still nowhere near cumming.

Deanna said to Jenna "I don't think I can do it through his jeans!"

Jenna said "So take them off."

"Do you think I should?"

"You might as well now. What's the difference?"

Deanna turned to me and said "Do you mind?"

I launched my arm at my zipper and had my pants and underwear off in no time. My throbbing, erect cock stood eagerly at attention.

"Ooh..." Jenna sighed.

"Nice." Deanna said.

She wrapped her hand around my shaft and started pumping, slowly at first and then steadily faster. I just lay there moaning with my eyes rolling back in my head. After awhile she laid down beside me cradling her head on my shoulder, never taking her hand from my erection. She kept fondling and pumping me for about 15 minutes and I still was nowhere near cumming, not that I wasn't enjoying myself! She whispered in my ear, where Jenna couldn't hear "If it will help you, you can put your hand down my pants."

Deanna was a very skinny girl and she always wore very loose jeans. I easily slipped my hand under her jeans and underwear without Jenna being able to see what I was doing.

First I slowly rubbed her ass with the palm of my hand, squeezing it gently and checking out her curves. In all the time I had known her I had no idea that Deanna had a great figure hiding under all of those loose clothes she wore! It turned out that under all that tom-boy clothing, she was really fine! She had one of the cutest, curviest little butts I'd ever had the pleasure of touching.

I reached down the crack of her ass and found her slit. I wasn't the only one enjoying this! She was already so wet that I had no trouble at all sliding my finger into her. She was so skinny I had no trouble getting it in deep. She had an amazing pussy! The inside wasn't just soft and formless like most girls. Hers was lean and had a sort of ridged texture to it, almost herringbone. It was great. I rubbed her g-spot for awhile and then moved my finger back out to her clit and began circling and gently pinching it. All the while she slowly gave me the best handjob of my life. After about 5 minutes of this I could feel myself getting ready to cum.

"I think I'm going to cum!" I said.

"Good. About time" Deanna said as she picked up the pace.

I started fingering her faster, still without Jenna knowing, and my cock started to pulse. First just a little cum leaked out, then a little more, then I erupted all over my own stomach and Deanna's hand and lower arm.

"Oh god!" I said "No one has ever been able to do that! You're unbelievable!"

Deanna smiled coyly and said "Thank you."

Then we just laid there holding each other for awhile, talking to Jenna about what had just happened and how wierd, but cool, it was. After a little while Jenna told us she had to get home and Deanna was her ride. So we all got in the car and drove to her house. She said goodbye and headed into the house, I'm sure to masturbate like crazy.

Then Deanna and I went back to my house to continue what we had started.