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Helping a Friend's Friend

I help my friend's best friend with his virginity.
During several “teaching” sessions with my young neighbor boy Timmy, he would bring up his best friend Scott. Timmy would tell me that Scott was very shy with girls and awkward around them. Timmy told me that his own confidence with girls had soared since I helped him with his virginity and gave him lessons on how to please a woman.

It seemed a little odd to me that we were both lying naked in my bed talking about Timmy’s best friend while Timmy’s cum was seeping out of my pussy. Timmy told me that Scott, his best friend who is a tall skinny nerdy looking kid, was constantly being picked on the popular girls in school. These girls would often act like they liked him, trying to get him to ask them out, only to embarrass him and make fun of him with the other school kids watching. Timmy told me that his friend Scott had withdrawn and was now afraid to even talk to girls. I finally said to Timmy that I felt bad for his friend but wasn’t sure why he was telling me all this.

Timmy looked down saying that he would love it if I could somehow give his friend the same confidence I had given him. He said that his Scott was really down and he was really worried about him.

I said, “Cut the shit Timmy, are you asking me to fuck your friend so he won’t be a virgin and that will give him the confidence to ask out girls?”

“Well when you put it that way, I guess I am. I know it’s a stupid idea just forget I said it.” Timmy put his head down like a whipped puppy.

I felt bad I had snapped at him so I reached over and stroked his soft cock. “I’m sorry but you had better not have told him that we have been fucking.”

“Oh no, I wouldn’t have done that. I know your husband would kill me. I just thought that if you did for him what you’ve done for me it would help his confidence.”

The idea taking Timmy’s friend’s virginity intrigued me; I have always had a soft spot for awkward boys and it really pissed me off that the “popular girls” picked on guys like him. While I was lost in thought about Timmy’s friend I hadn’t noticed that Timmy’s dick was back fully hard from my stroking and that I had been rubbing my pussy with my other hand. “I’m not saying yes, but if I did say yes, how would you propose we get him here.”

“Well Scott knows I have a date Friday night, I could tell him that I had agreed to help you with something Friday night and needed him to take my place,” Timmy suggested as his breathing got heaver from me jacking him off.

I moved over Timmy straddling his cock guiding it into my pussy. The idea of fucking his friend had gotten me very horny.

I told Timmy as we fucked again, to set it up but I was still not saying yes. I told him not to tell Scott anything other than to show up and be ready to work. I would decide then if I would fuck him or not.

I also knew that I had to ask Sam if he would mind. I already knew that he wasn’t going to be home Friday night, so that wouldn't be a problem. When I asked Sam, he made a joke of it, but in the end told me that if I could help the kid’s self-esteem to go ahead. At first I was a little mad at him for joking, but he did show his sensitive side in the end, telling me that I was helping the kid.

My next problem was how to do it. I ran though several scenarios in my head that ranged from dressing like a slut to spilling a drink on his crotch. I really didn't like anything I came up with so I decided that I would just going to talk to him about girls and see where it went.

Friday night arrived and I was wearing skirt and a silky top that showed my cleavage such that it is. The silky material made the nipples very visible with no bra on. Scott knocked on the door and looked as nervous as I would have guessed he would. Scott is a cute boy with a nerdy look. He is tall about six foot one and skinny. Scott had a hard time taking his eyes off my hard nipples as we chatted.

I thanked him for filling in for Timmy and explained to him to boxes of things I needed moved. Scott mentioned that Timmy had told him that I had helped him with girls so he could ask a girl out and hoped I didn’t mind if he asked me some questions. I told Scott that I would love to help him so he would be more comfortable with girls.

It didn’t take long to finish putting the boxes away. I asked Scott if he wanted to practice asking me out.

“Really you would do that for me?” Scott asked

Scott and I role played for a while with him asking me out. I even switched roles and showed him how I would ask him out. When I thought he was getting it okay, I told him that he should practice how to act on a date. I told him to hold on for a second and I would be right back. I ran upstairs to my bedroom and grabbed a bra. I had the idea that I would give him a chance to remove a bra on a date.

Scott asked me what he should do?

I told him first he should tell his date how pretty she looked if you think she looks pretty.

Scott said, “Oh ma'am you look gorgeous, very pretty.”

“Okay Scott, I’m just Taylor and I’m your date, not mam.” I told him. I told him to escort me to the couch and we would pretend we were at the movies. I turned down the lights and we sat down on the couch. I sat in close to Scott that he should complement the girl if she is perfume. Scott leaned into my neck to get a good smell.

“Oh yes you smell wonderful,” Scott said.

“Okay now put your arm around me,.” I told him. Scott did as he was told and snuggled in close to Scott. “Scott, have you gotten to first base with a girl?”

“What do you mean first base,” Scott said

“You know first base, kissing. You’ve heard of the baseball analogy in making out.” Scott shook his head no. “That’s okay we will go through it, have you kissed a girl?”

“Just like mom and aunts and stuff.”

“Then you need to try a real kiss, bring you lips over here.” Our lips met and I told Scott to loosen up his mouth which was locked tight. Scott opened his mouth giving me a chance to use my tongue. Scott got the idea and met my tongue with his. While we were kissing my hand fell across his lap and found Scott’s cock very hard. Scott let out a moan my hand rubbed across his cock.

We kissed for a bit and then I asked Scott if he was ready to try for second base. Scott gave me a confused nod; I could tell he didn’t know what second base was. I whispered in his ear that second base getting under the girls shirt and feeling her tits. I took Scott’s hand and moved it over my breast, just rub it and squeeze it gently. “Okay I haven’t stopped you, so move your hand under my blouse and feel my tits over my bra.

Scott again did as he was told; he rubbed my hard nipples through the lacy material of my bra and squeezed my tits. “Scott reached around my back and try and unclasp my bra.” Scott reached behind me and fumbled with the clasp. “Keep trying you will get it.”

“I got it!” Scott shouted as my bra came undone. He reach his hand back and found my now free naked tits under my shirt.

To his shock I reached back and re-clasped my bra. “Try it again be a little more subtle when you get it.” He got it much quicker this time and slid his hand underneath the bra.

As Scott fondled my tits I asked him how he liked second base. “Mmm I like it a lot, can I see them?” Without saying anything, I pealed my blouse off and finished removing my bra.

“Better?” I asked as Scott just stared at my now naked tits. “My nipples like to be kissed and sucked on.”

Scott quickly moved his head down putting him mouth on my tits. While he kissed and licked on my tits I move my hand down to Scott’s crotch. Scott moaned again as this time I squeezed his hard cock. He stopped licking my breasts and moved his mouth up to mine. As we kissed I continued to stoke his dick.

I broke the kiss, asking Scott if he wanted to try for third base.

“Sure, how do I get to third base?” he asked.

“You put your hand under my skirt and panties to rub my pussy.” Scott just looked at me not moving. I took his hand and place it under my skirt on top of my panties. “Now move my panties aside and let your fingers find my pussy.”

It was my turn to moan as he rubbed my pussy lips and slipped a finger into my very wet pussy. "Mmm do you like how wet I am for you?"

"Yes it is very nice, it feels great."

 I squeezed his dick hard and said to Scott, “How about we go up to my bed and you can get this hard dick to home plate.” Again Scott looked at me with a puzzled look. “We don’t have to if you don’t want to.”

“No, I want to; I just don’t know what to do,” Scott said.

We stood up and started upstairs. “It’s real easy, I will show you what to do. I will lay on the bed spreading my legs. You get between my legs and put your cock in my pussy. Keep moving you dick in and out of my pussy till you cum in me.”

As we got to the bedroom I slipped my skirt and panties off and moved to Scott helping him off with his cloths. I removed his shorts and underwear finding a nice cock pointing at me.

Kneeling in front him I said, “Mmm that’s a nice dick, about 7 inches right.” Before he could answer, I took the head of his cock in my mouth sucking on it.

“Oh shit that feels great,” Scott moaned as I sucked on his cock.

“It’s going to feel even better when you are cumming in my pussy.”

“Do I need protection?” Scott asked.

“Good boy for asking, I’m on the pill so it’s ok for you to shoot your load in me.” I said to Scott was bucking him hips into my mouth and I figured that if I kept it up he would cum. I wanted that first load to be in my pussy so I pulled off his cock climbing on to the bed. I spread my legs wide, “I think it’s time for you not to be a virgin anymore.”

Scott climbed over top of my and I lined up his cock with my pussy, “Now go slow and try to make it last.” We both moaned deeply as he slid in my dripping pussy. “Now start pumping your cock slowly in and out of me.”

“Oh God that feel’s great,” Scott said as he pumped his cock into me. Scott's dick was sliding in and out of my very wet pussy. A short time later Scott grunted and slammed his dick into me hard. I knew he was cumming. “Oh I’m sorry I couldn’t hold back.”

“It’s okay, how was losing your virginity?” I asked him as I could feel his dick softening.

“That was incredible, I love fucking I can’t believe it. Timmy asked you to do this didn’t he?”

“Yes he did, but you can’t tell anyone that we fucked.”

“Oh I won’t.”

I leaned up to him and gave him a passionate kiss using my tongue like I was fucking him mouth. I could feel that his dick was growing as we kissed and I was moving my hips.

“I think your cock is ready for round two don’t you?”

Scott had already started pumping his dick back and forth as he moaned, “Really can we?”

“Roll over I’m going to show you how it feels with me on top,” I told him as I moved over top of him.

I lined up my pussy with his cock and slid down on him. I told him to just lay back and let me be in control. I moved his hands to my tits and told him to play with my tits and squeeze them as I fucked him. I shifted around so his dick was hitting all the right spots. I started humping on him faster and harder till I could feel my own orgasm building. “Oh fuck yeah Scott, your cock feels great inside me. I’m about to cum.”

My body was shaking and my pussy muscles squeezed Scott’s dick hard as I had a strong orgasm. I was too caught up in my own orgasm to notice the effect I was having on Scott. He let out a loud grunt as he shot another load into me. We both relaxed as I collapsed on top of him. I slid up Scott’s body so his dick flopped out of my pussy and his cum was dripped on Scott’s belly. I kissed Scott and told him that his lesson was done.

“Did I pass?” Scott asked.

“That was lesson number one. You’ve got a lot more to learn.”

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