Teaching Her Friendsbypeanutbutterjellytime©
I met Jill online. We had very similar views about a lot of things, and when we met in person we could tell intuitively that we could trust each other. Neither of us had any romantic interest in the other, but we got along great and enjoyed the same things, so we wound up hanging out frequently, especially after the following event.
It was the first time that Jill had invited me to her house. She shared it with two other women, Melissa and Caitlyn. Jill made a light dinner which we all shared and we talked and by the time we were done we were all quite comfortable with one another.
And just like that, out of the blue, Jill asks me:
"Oh, could you help us with something? I wanted to teach these two how to give a first-rate handjob."
I blinked a few times, and then a few more, trying to make sure that I had heard her right.
"Uh," I stammered, "how exactly can I be of help?"
"Well telling them about it is all well and good, but I think it would be better if they had a hands-on tutorial," Jill said with a wink. I was still stunned and hadn't come up with a response when Jill made up my mind for me. "Come on, now, it's for the common good. We wouldn't want their future boyfriends to miss out on mind-blowing handjobs, would we? No. Now follow me."
With my brain temporarily out of service, Jill took my hand and led me up to her bedroom, Melissa and Caitlyn following behind.
"Your job is simple," said Jill. "You just be your handsome self, and just sit back and enjoy the ride. But first, I'm going to need you to take off your pants."
The girls were enthusiastic but I hesitated as I started undoing my belt, feeling something akin to stage fright.
"Maybe it would be easier for you if you were blindfolded. You can pretend whatever you want and don't have to think about everyone watching you," suggested Jill.
"Um, okay, that makes sense," I said.
Jill pulled what looked like a very wide piece of ribbon from a drawer by her bed. I briefly wondered what else she might have stashed in that drawer as she tied the blindfold around my head. She wrapped her arms around me and gave me a little kiss on the cheek, then slid her hands down my body and squeezed my ass.
"Now let's see what I've got to work with. Drop 'em!"
I finished undoing my belt and, resolving to go through with this, dropped my pants and boxers to the floor in one motion. This action was met with murmurs of approval from my audience. I'm only slightly above the national average in penis size, but I fall in the "just right" category for a lot of women. I tried to suppress a grin.
"Ahh, very nice... it looks like you're enjoying this," Jill traced her fingernails up the sides of my bare thighs, bringing me to a full erection. I could feel her breath on the tip of my cock, and shuddered with anticipation.
"Lie down on the bed, and get comfortable." Jill helped me onto the bed, gave me a light pat on the thigh, and stood up. I heard her open her drawer of tricks again. "Now girls, the first rule of handjobs is: lube, lube, and more lube! Melissa, I'm going to need your help in a moment. Thanks."
I heard her open a bottle and squirt a liquid into her hands, and then a shlick-shlick as she rubbed them together.
"If he weren't completely hard already I might tease his inner thighs a little bit first... but I think we can go straight to the main event." And she did. Her hands wrapped around my cock, squeezing and massaging the lube all over the length of my shaft. Her hands went in long, slow strokes from the tip to the base and back again. I stretched my arms out and sighed a contented sigh.
She kept that up with one of her hands while the other one caressed my balls, testing the weight in her hand, and then cupping her fingers around them.
"Okay, Melissa, go ahead."
I felt metal clasp around one of my wrists. Startled, I tried to sit up, but Jill squeezed VERY firmly on my balls until I lost my strength and all I could do was whimper. Melissa pulled my arms together and cuffed the other wrist.
"There's a rope you can attach those to under the bed," Jill told Melissa as she maintained the pressure on my balls and continued to lightly stroke me. I felt something pull on the handcuffs until they were taut. I guess Caitlyn figured out what they were doing because a third pair of hands bound my ankles as well. I was stuck there until they decided to let me go. Which, I thought, as Jill's skilled hands worked me over, was not so bad.
Jill explained to Melissa and Caitlyn what she was doing as she stroked, twisted, squeezed, teased, tickled, swirled, and stroked some more. I usually have a lot of stamina, but she was a real pro and it wasn't long before I was moaning and writhing.
"There's no need to fight it, boy... I'm not going to let you come yet." And she didn't. Jill showed Melissa and Caitlyn how to keep me right at the edge, slowing down and speeding up at just the right times, using upstrokes and no downstrokes, running one finger along the length of my shaft, making it twitch and jump.
Just when I thought I couldn't take anymore, Jill stopped her torments and slid her hands up my chest, wiping off the excess lube. She climbed on the bed next to me and kissed me. "I don't think we need this anymore," she said as she pulled off the blindfold. "But don't worry, we're just getting started." She gave my cock a hard SMACK! and got off the bed. "So who wants to try first?"
Melissa was first. It was obvious that she wasn't as experienced as Jill, but she was a fast learner and being as I hadn't completely cooled down from Jill's working over, she had me squirming in no time.
"Careful, Melissa, he's going to come soon," Jill said. "It's an incredible experience for a man when a girl brings him off, but it makes a mess!"
"I want him to come on my tits," said Melissa. "Guys go crazy for that, right? Do you want to come on my tits?"
I gasped an affirmative as she took off her shirt.
As per Jill's instructions, Melissa grabbed onto my dick with both hands and started pumping like crazy, her large breasts hovering just above. "Oh yeah... come for me, come all over me..."
I wasn't about to let her down. After all of Jill's teasing, I had a monster load ready to blow, and with a moan that was almost a scream I covered her breasts with cum.
My ears were ringing and I was dizzy, but I could still hear Melissa squeal with delight. Through my half-closed eyes I saw her lift one of her breasts up to her mouth and lick it. If my hands weren't bound I would have pinched myself to see if I was dreaming.
While I was coming down from my orgasm there must have been some removing of clothes, because the next thing I remember a naked Jill cuddled up next to me and cradled my face.
"What a performance! You're being a very good boy and very, very helpful. But we're not done with you yet. We're going to need you hard again. Do you think you could do that for us?" Jill must have known I was too wiped out to reply, because she continued, "Mmm, I think I know what kind of encouragement you need."
She kissed me again, slowly and deeply, and then broke away suddenly, a hunger in her eyes. She brought one of her breasts to my lips. "Suck on it." She had a way with words.
Awash in bliss amongst her ample cleavage, I sucked, licked, nibbled and bit Jill's nipples, while she moaned and held tightly onto my hair. At least one pair of hands started lightly scratching my inner thighs and idly playing with my genitalia, more curious than anything else.
Jill was enjoying my minstrations but was unsatisfied. She pulled her nipple away from my mouth with a POP! and got to her knees. "Let's really put your tongue to the test," she said, and straddled my face. "I'm so fucking horny! Ohhhhh god, lick my pussy!"
She certainly was horny... as soon as her pussy made contact her juices started to drip down my chin. I started using every move that I knew, utilizing every inch of my tongue, lips, and even nibbling with my teeth, assaulting her wet snatch like the hungry dog that I was.
Not surprisingly, Jill's sexual agression (and, quite possibly, her moans and shudders) got me hard again. I could feel a pair of hands start stroking my dick in earnest... they felt different from Melissa's, so this must be Caitlyn. She wasn't quite as skilled but her enthusiasm was much appreciated!
After a few minutes of this, Caitlyn's stroking lost some of its vigor and she asked Jill for some tips. Jill gave a frustrated grunt and reluctantly dismounted my face. She knelt beside Caitlyn and started giving her tips and cheering her on, a bona fide handjob coach. A thought flashed in my head of Jill and I going into business as a handjob instruction team.
"This is a lot of work! I'm getting tired," Caitlyn said, her stroking slowing down a little bit.
"I'll let you in on a little handjob secret then," Jill said, as she went back to her bedside drawer of tricks. "An advanced technique." She took something out but I couldn't see what it was. Caitlyn took her hands away from my cock and there was some whispering and giggling and activity below my field of vision. Finally Caitlyn looked at me with renewed excitement and a gleam in her eye.
One of her hands started stroking me again, and then I felt a light pressure on my anus. Caitlyn teased around the rim of it for a bit, then started tapping it with increased pressure. Her eyes were fixed on my face in excited curiousity. Slowly she eased her finger inside of me, her other hand still stroking my dick. She timidly -- as timid as someone can be when they have a finger up your ass -- searched around until she found my prostate, which was confirmed by a jump and a moan from me, and got into a rhythm of lightly massaging my prostate and jacking the entire length of my cock.
Words were exchanged by the girls but I didn't hear as I let myself get lost in the sensations, until I came a second time, back arching and cum shooting straight up in the air. As my post-orgasmic spasms started to subside, Caitlyn made sure to squeeze out every last drop of cum, and it dripped down over her hand. I don't think I've ever seen a woman look so proud of herself.
The three women cleaned up the mess that I made, but I had a feeling that they weren't done yet. They were all still visibly excited, glancing at me and my cock lasciviously.
"Well," announced Jill, "this concludes the educational portion of our evening. Now it's just for fun." She grinned at me as the others helped her to untie my legs and turn me over, re-tying me so that I was kneeling on the floor with my torso face-down on the bed. Jill lay on my back, her naked breasts and rock-hard nipples pressed up against me, and whispered into my ear: "For what we're about to do to you, I hope that you'll pay us back in kind some day soon."
"All right, girls," she said, getting back to her feet. "Who wants to spank him first?"
I don't know who went first, but they all had a great time as they smacked my asscheeks, making sure to get every inch dark pink; sometimes slow, powerful and deliberate, sometimes rapid-fire... sometimes both cheeks at once. I enjoyed every minute of it, pleasure mixing with pain... especially when two of them went to work on my cheeks, alternating hard fast slaps and rough kneading, while a third pair of hands squeezed my balls and once-again hard cock as I moaned into the bed.
Finally, my ass red and sore, the three of them grew tired and turned me back over again. They were breathing heavily both from the effort and from excitement, and I saw Melissa's hand sneak down into her pants.
"Looks like you're ready for more," Jill leered. "It would be a shame to let that hardon go to waste." She practically jumped on top of me and roughly grabbed my dick, lubed it up sloppily and started going to town. As my mouth opened to let out a moan, she brought her leg around and lowered her pussy over my face in a classic '69' position. She was twice as wet and twice as excited as before, grinding her pelvis into my face, hands working furiously. All I could see was Jill's jiggling asscheeks, but I could hear Melissa and Caitlyn moaning, and I assumed they were masturbating while watching the assault on my cock.
Jill proved that she was a master as I shot my load once again, moaning into her pussy. Her gyrations on my face became even more rapid and desperate as she kept stroking my cock, my brain got lost in the overload of sensation but somehow I managed to keep licking her clit and then she was coming, gushing her sweet liquid all over my face, screaming and arching and then she collapsed and rolled to the side, her hands finally releasing me, panting and shuddering and laughing and grinning.
As she was catching her breath, still panting and gasping, Jill crawled over and untied me. I rubbed my wrists as she gently cradled my head and licked her juices from my face.
"I think you should stay the night," Jill said softly. "You're going to need your strength for the morning, when we tie up Melissa and Caitlyn."
I stayed the night.