Jerking off a virgin twice [F18][MassageParlor]

Walking into the room, Jenn saw a boy right around her age. He was incredibly short and skinny with worried eyes and a bad haircut. He was also fully dressed, yet his hair was wet.

“Did you already shower?”

“Yes, yes I did,” he nervously replied.

“But then you put your clothes back on?” Jenn questioned.

“I wasn’t sure… so I… umm… I – ”

*Another complete newbie!* Jenn moaned in her head, then resigned herself to wear her kindest smile and drag this poor young man across the finish line.

“Ok… well, sweetheart, what is your name?”

“Umm… I don’t think I should – ”

“Tommy… your name is Tommy. Why don’t you take your clothes off and get on the table?”

“Ok….”

“Are you from around here, Tommy?”

“Yeah, I’m a freshman at the University,” he whispered, as if it were a secret.

“Is this your first time here?”

“Yes.”

“Ok, take off your clothes and I’m going to be very gentle with you, ok?”

“Ok,” he agreed, then took off all of his clothes, but became very embarrassed when it came time to take off his abysmally unattractive white briefs because he had an erection protruding from inside.

“All of it… those too!” Jenn snapped, talking to the young man as if he were a small child and not her age.  

The Freshman dropped his briefs and hopped up on the massage table as if it were a doctor’s office. He did his best to use both hands to hide his prick, which was standing at full attention.

“Ok, Tommy, I’m going to tell you everything before it happens so it won’t surprise you, do you understand?”

“Yes.”

“Ok, you’re going to lay on your back and uncover yourself. You specifically showed up here for this and I’m going to put oil on your dick and then I’m going to very gently touch it. I want you to relax, do you understand?”

“I do!” he excitedly whispered.

“Have you ever jerked off before?”

“Oh, so many times!” he replied with a little more confidence.

“Well, I’m going to do the exact same thing. When you’re ready to cum just do it, ok? Don’t worry about anything. Just stay relaxed, ok?”

“Ok!” he breathed.

Jenn went over to the cart and retrieved the giant bottle of oil and walked it to the quaking young man splayed out on the bed. He had placed his hands along his sides and closed his eyes. He was skinny, and pale with little muscle tone but he wasn’t unattractive.

*Probably a flat virgin!* Jenn surmised.

She squirted a healthy dose of oil into her hands then gently wrapped them around Tommy’s quivering prick. He was circumcised and well groomed. His penis was very clean, symmetrical, and not unpleasing to the blonde teenager tasked with rubbing it. She gently gripped his cock and slowly began twisting and sliding her hands up and down the shaft.

“OOOHH!!” Tommy jolted, then bucked as a massive spurt of semen erupted from his shaft.

“Gooooood!” Jenn soothed as she continued to stroke.

“HHHHHAAAANNNN!” he continued to groan as burst after burst leapt from his throbbing head. The semen pirouetted in the air and fell back directly on top of Jenn’s hands, still gliding.

In total, Tommy grunted and shot no less than six bursts into the air. When he was finished he gasped catching his breath.

“Wasn’t that nice?” Jenn soothed.

“Ahhh! Yes!” the young man breathed.

“Now, turn over and I’ll give you a massage,” Jenn comforted.

The man turned over and she dripped oil all over his body, lovingly rubbed into his shoulders, his back, his neck, and his arms. When she began to massage his ass at first he became noticeable uncomfortable but then settled down and enjoyed the blonde girl in his class grind her hands into his ass cheeks and even slide her fingers along his crack. As she slide, he started to become aroused again.

“We’re going to make you cum a second time, ok?”

“Yes!”

“But before we do, I need you to give me my tip. You understand that I need a tip, hon?”

“Yes… how much?”

“I usually get a hundred, but that’s only for once. I’d like you to give me another hundred for the second time, ok?”

“Two hundred is fine!”

“We can do other things if you’d like… doesn’t have to just be my hand…,” Jenn eased.

“Well… I could take off my top… I could use my mouth and suck you… ,” she winked.

“Oh! Yes! Please!” Tommy begged.

“How much money do you have?” she queried the naïve young man.

“I brought four hundred… I gave the woman one so I have three left!” he announced.

“Are you a virgin?” Jenn sweetly asked.

“Well… I mean… I’m technically… yes, I am,” Tommy stuttered.

“Have you ever kissed a girl?”

“Only once but it didn’t go very well… I tried to kiss a girl in high school and she… well she got upset… and it wasn’t a real kiss… she didn’t kiss me back,” he admitted.

“Have you ever touched a woman?”

“No, I haven’t.”

“Would you like to?”

“So much… it’s all I think about!”

“Ok, you’re going to give me the three hundred and I’ll be instructing you, so you don’t have to worry. First, I’m going to kiss you, just so have that out of the way! Then I’m going to get naked for you. I’ll help you to touch me, so please let me guide your hands. Then I’m going to make you cum again, but this time with my mouth, alright?”

“Yes! Yes please!” the Tommy blurted.

“Ok… I’m going to kiss you… take your time… don’t get aggressive… just relax,” Jenn instructed.

She helped Tommy sit up then stepped into his hips and leaned into him, angling her head, until she was able to touch her lips to his. At first, Tommy was incredibly awkward, misaligning his lips with Jenn’s, not opening his mouth enough, then opening his mouth too much. At first he hid his tongue from Jenn’s inside of his mouth, then finally reciprocated Jenn’s playful licks. After a few moments, he was passably making out with the pretty blonde.

“Good!” Jenn praised, pulling back from the hungry mouth. “Now, I’m going to get naked. Just sit there and I’ll help you to touch me correctly. Now remember, girls don’t want to be roughly touched. Always be gentle,” she instructed.

Tommy’s eyes grew wide as Jenn peeled off her tank, unhooked her bra, and slid down her stretch pants and thong.

“Open your hand like you’re going to pick a nice apple… but don’t be rough! They’re delicate apples,” Jenn told the man.

He reached out with open hands and Jenn stepped into his reach. Tommy gently grasped her both of her breasts at the same time.

“Never pinch my nipples… cup them… touch but be gently… very good… very good, Tommy,” she praised.

“Oh… oh my…,” Tommy cheered as he fondled.

“Now I’m going to help you to touch my pussy. I don’t want you to do anything… just let me control your hand, ok?”

“Yes!” Tommy breathed.

Jenn took the hand off her breast and spun it so Tommy’s palm was facing up, then she brought it underneath her so the fingertips were touching her labia.

“Be gentle…,” Jenn soothed.

Tommy’s fingers quivered and felt rather good on Jenn’s exposed lips. She carefully rolled back all of his fingers until only his longest finger was still extended. Jenn leaned over and lovingly sucked on the finger then raised her torso and gently slide the finger inside of her vagina.

“Oh!” Tommy quivered.

“That’s what a pussy feels like… don’t you think that would be amazing for your cock to feel?”

“Yes!” Tommy tremored.

“Now taste your finger,” Jenn instructed as she slowly pulled the finger out.

Tommy sucked on his finger as if it was coated in the purest of chocolate.

“Can we have sex? Please!” he begged.

“Let’s save something for next time, ok? Now, are you ready to have a blowjob?”

“Oh… oh yes! Oh yes!”

“Now lay back down and leave everything to me,” Jenn smiled.

Tommy quickly laid on the table and excitedly waited for the naked girl to perform a sex act on him that the young man had craved for half a decade.

Jenn was feeling aroused having been touched by a gentle young man. She might have been able to supress her desire to orgasm, until she was fingered. Still, Jenn knew that Tommy was not the correct man to scratch that itch; he’d be cumming buckets the moment she had him inside of her and would have no opportunity to gratify herself.

“Hopefully someone will come in today that I’d enjoy fucking,” Jenn whispered to herself as she hovered over Tommy’s erect cock and grasped it firmly before taking it into her mouth.

“OHHH!” the man gasped as Jenn began rhythmically slurping up and down his cock.

Had Tommy not been jerked off thirty minutes prior he wouldn’t have lasted five seconds in the blonde’s mouth. Instead, he lasted an entire ten seconds.

“OHHH! AHHHHRRRRRREEEEE!” Tommy groaned and began cumming into Jenn’s mouth.

Not wanting to ruin his experience, Jenn, regrettably, began swallowing each spurt in order to ensure Tommy would never experience a diminished pleasure. With his back arched, his hand’s pressed into the table, howling into the halogen lights overhead, Tommy entered the coven of sexually experienced men.

“How was that, Tommy?” Jenn asked, knowing he derived a level of pleasure that only heroin addicts and teenaged boys getting their first blowjob would understand.

“The most amazing thing… the best! I… oh my God!” he belted.

“Well good! Now get dressed and go home. Next time you come we will take your virginity… unless you lose it to some lucky girl in the dorms, now that you know how to kiss,” Jenn praised.

As Tommy slowly rose from the table, Jenn quickly dressed then left the room three hundred dollars richer.

“Jenn… I have another customer ask for you… room two!” Galina barked at the blonde.

Source: reddit.com/r/eroticliterature/comments/oq4isk/jerking_off_a_virgin_twice_f18massageparlor