The Sex Tutor
 

CLIENT: STACY
Stacy was a sophomore in college and she was a self-confessed "hopeless virgin." She was extremely awkward and deathly afraid of starting conversations with guys let a lone getting involved in a relationship. She was raised a strict Catholic but longed to have a real boyfriend. She wore thick glasses and had long straight hair. She was book-smart and often carried her books in front of her chest. Stacy constantly had her head down and avoided eye contact with everyone except for her only confidant - James.
With James, Stacy could open up and share her concerns and feelings. He was always there for her and he was an excellent listener. He often gave her advice but she rarely had the courage to try his advice in the real world. One Friday night they were alone in her dorm room. They were gabbing as they often did about there day. Stacy broke down crying. She explained that she had her first date with a guy and it was an absolute disaster. James sat next to her and asked her to explain further.
I went to the frat party and ended up in a really cute guy's room. We were both drunk and he put my hand down the front of his jeans! I had his cock in my hands! James smiled and said, "That's great Stacy - you've been dying to have a boyfriend."
"I was awful!" confessed Stacy. I didn't know how to ah - ummmm get him off. He laughed at me James and looked at me with disgust. I will never date again! I'm so useless!”
James held her in his arms quietly whispering, "It's alright sweety. You will always have me to rely on."
Stacy looked up slolwy and locked eyes with James through all the tears. Would you really help me with anything?
James replied surprised, "Of course - I'd do absolutely anything for you."
Stacy sat up taller and wiped the tears from her eyes which only streaked the little bit of eye liner she used.
"James - will you teach me how to touch a man?" she asked.
"That's simple Stacy - do you want a hug? We've hugged hundreds of times…"
"No James, I need to learn how to touch you down there - looking at James' crotch."
"Oh myyyyy God" said James in the most astonished tone Stacy ever heard.
"Ummmm - I guess so" stated James after a long awkward silence.
"I don't want to have another man laugh at me James - pleaseee."
James propped himself up on Stacy's bed. He leaned back against the wall. His heart began to race and pound within his chest and his hands started to tremble. Stacy touched his stomach and massaged his chest. She reached down to the front of his pants and unbuckled the belt and dropped it onto the floor. James could see Stacy's hands were trembling too. She slowly unzipped the top of his pants and he felt his penis slither in his pants. He went from soft to medium hard in an instant. Stacy saw the outline of his cock and remarked, 'My God James - you're really big."
"Thank you" he replied.
She pulled the zipper all the way down and began to see James' black bikini briefs. She curiously pulled the top of his undies down and saw the rim of his blond pubic hair.
She whispered, "Ohhh."
She continued pulling downward until she felt his erect cock head stuck underneath the underwear band. She needed to reach in with her other hand and hold back the band to get to his cock. James moaned and closed his eyes. She gripped the staff shaft and tugged James pants and undies down to his shoes. This was the very first time she had ever seen a man up close. She thought to her self how amazingly beautiful he was. She was surprised at how soft his scrotum was. she firmly pressed into the center of his ball sac and he jumped a bit. "Easy down there Stace."
Stacy responded, "Sorry."
James reassured she was doing just fine.
Stacy asked coyly, "What do I -- ahh do?"
Run your hand up and down the shaft. Relax. Realize that it all feels great for the man. Mmmmmmm that’s good.
“Oh my God – your veins are showing. Is that normal with every guy?”
“Yes, some veins show more than others.”
Suddenly, Stacy felt the urge to taste him. “James?”
“Yes, Stace.”
“Can I taste you please?”
“Yes you can sweety – help yourself.”
Stacy took a last glance over at the dorm room’s door and made sure it was locked before putting her face a few inches from James’ penis. She smelled a mixture of soap and cologne on his body and she loved it. She gripped his swelling cock and lightly touched her tongue on the back of his shaft. James let out a soft moan. Stacy pressed her tongue harder on his shaft and ran her tongue up the back of his thick cock. She licked again and again each time getting closer to the tip. She couldn’t stand it any longer. She inserted his entire swollen cock head into her mouth. She smiled slightly to herself as she felt his penis slither around in her mouth. She took his penis out of her mouth and a line of drool and pre-cum dribbled down her chin. She wiped her chin quickly and smiled with embarrassment. James reassured her she was doing great. She began gaining confidence and momentum and quickly shoved his prick back in her mouth. She held the base of him firmly and angled the hard cock straight upwards and seemed to be enjoying allowing his prick to spread her lips apart as she pushed her face into his crotch. She experimented with taking him deeper and deeper in her mouth until she gagged when his prick tickled the back of her throat. She quickly took his cock out of her mouth and started coughing and laughing.
James whispered, “Take your time – you’re awesome.”
Stacy looked up at James from his groin area and asked, “What does deep throating mean? I hear the girls in the locker room talking about it”
James, “It’s when you let the penis go to the back of your throat. That way when a man cums, you don’t taste it. The sperm just goes right down your throat in an instant.”
Stacy thinks quietly for a moment. “But I want to taste it – is that wrong?”
“No, it’s fine. Do you want me to tell you when I’m cumming?”
“No it’s alright, I want to be surprised. How about if I just keep my mouth open and you can shoot it inside my mouth as you umm play with yourself.”
“That’s perfectly fine. Are you sure Stace? A lot of girls dislike the taste,” warned James.
“Yes I want it in my mouth. I’ve been thinking about it for a few years now.”
“OK sweety.”
James stood up and began jerking himself hard. Stacy felt her heart racing with excitement. She closed her eyes and opened her mouth wide. She heard James let out a really loud moan and she couldn’t believe how warm the cum was in her mouth. In fact, she had a line of cum on the side of her cheek. He spurted at least six times. She waited until he stopped squirting and then closed her mouth. She felt the ball of cum in her mouth and she really loved the taste and smell. She swallowed hard and felt a surge of sperm coarse down her throat. She even wiped the cum on her face back into her mouth and swallowed that as well. She smiles looking up at James. He looked at her and smiled too.
“Again” she whispered.

Part 2
 

CLIENT: Jocelyn
A few weeks went by for James and nothing much new happened until he got a call on his cell phone from an older woman. She said her name was Jocelyn and she is the professor of Stacy’s American Literature class. James thought it so strange that a professor would be calling him on his cell phone.
Jocelyn went on by saying, “I have a proposition for you and your umm services.”
James queried, “My services?”
“Yes, I’ve heard from a very reliable source that you give special lessons.”
“Oh you must have talked to Stacy.”
“She’s one of the only students I can trust.”
“I see,” he replied with a widening grin.
“Well, I never thought this would become a business. I just tried to help a friend out by showing her how to give a good blowjob,” he said matter-of-factly.
“Well, I desperately need your help James. As you know, I am not a very popular person. I am very cranky and know it. I don’t generally like being around a lot of people. However, I’ve begun reading a lot of erotica and it made me come to the decision that I am really missing out by – well being a virgin.”
“Still?” James replied in complete shock.
“Don’t get wise with me dear. I was kissed behind the barn at home but that’s when I was a child.”
“What kind of money are you prepared to spend?” he asked.
“I have a huge inheritance so price is no object. I want hot sex from a young athletic man like yourself and I want it right now.”
“But you’re sixty-seven years old!” he cried.
“I’ll pay you one thousand dollars an hour to be at my beckon call whenever I want sex. If you tell anyone about this, I will make your life a miserable hell.”
“Where do you want to meet?” he asked.
“My beach house at 397 Oceanside Parkway in El Condido. Be there in an hour.”
The phone line went suddenly dead.

James knocked on the door and Jocelyn answered wearing a summer dress with purple floral designs. She wore horn-rimmed glasses and a lot of silver necklaces. Her hair was up and she had wrinkles on her neck and cheeks.
“Come in.” she said taking a step backwards.
She escorted me into her bedroom overlooking the ocean. The windows were open and breeze filled the room in gushes.
“Take your clothes off,” she stated firmly.
She sat in a Colonial chair and reached for her glass of gin. James felt her eyes focusing on him like a laser.
“I need to see you up close so come closer to me,” she commanded.
He pulled his t-shirt over his head and she seemed to have a half-smile on her face upon seeing a muscular, lean upper body.
“You are a beauty my dear. Come closer still.”
He stood with his surfing shorts and sandles directly in front of her as she reached up and stroked his chest. Her hands clasped onto his hips and kissed his chest warmly. She felt him arms and shoulders as if she had never seen a man before. She rubbed his biceps and let out a quiet gasp of joy.
He crouched down and gave her a soft kiss on the cheek. Her skin was soft and warm. She began to moan lightly and he kneeled in front of her and kissed her neck. She arched her neck back to allow me more access to her throat. Their lips connected. He felt her grab the back of his head and they kissed for a long while. She began to develop the coordination to breathe while kissing. Her tongue was warm. She took to tongue kissing right away although she occasionally had to stop to breathe. As he kissed her, he began realizing that he started to become erect. He was shocked. In fact, his biggest worry coming over was that he wouldn’t get excited. His cock was beginning to press against his shorts. She looked down at his hard-on and saw a small damp spot. She sat back and said, “I have to see it.”
James looked down at her eyes and saw the desperation and pain that she had been feeling for decades.
“Why don’t you pull my shorts down?” he asked quietly.
She reached her hands up and slipped her warm hands underneath the back of his shorts. She cupped her hands over his ass and pushed his shorts down exposing his manhood. She looked at him and admired the vein that pulsing in his growing shaft. Her hand reached up and gripped his hardness firmly.
“Beautiful,” she moaned.
She began to stroke him and loved how his skin moved with her hand. She brought her hand all the way down his penis to his scrotum. She moved her hand up and down each time moving closer to his crotch with her face. She noticed a tiny clear drop formed at his tip.
“As that what they call cum?”
James explained, “No, that is pre-cum. It helps to lubricate the inside of my cock.”
She broke the bubble of pre-cum and smeared it over his cock head. His head became very slippery. The pre-cum continued to trickle as she stroked. She cupped his balls and stretched his sac upwards and let it settle back down.
James crouched down to eye level and said, “Well now that I’m comfortable how bout if we get you more comfy?”
Jocelyn leaned back in her lounge chair as the breeze floated in lightly. James lifted the strap on her shoulder and released it to past her elbow. He did the same with the other side.
Jocelyn murmured to herself, “I can’t believe this is finally happening.”
James buried his lips into her luxurious neck. She makes a point to take excellent care of herself, exercising religiously everyday. The feeling of his hot tongue on her neck made her to become moist. The front of her dress began to slip downward exposing her bare breasts. Her breasts were full and shapely. Her nipples were pink and erect. Her nipples hung down just a bit but were still amazing to look at. James couldn’t help sinking his face into her breasts. He raised her shapely tits upwards with strong hands. He latched his lips over one of her nipples and sucked it inside his mouth. He felt his mouth fill up with her breast. He massaged his face in between her boobs until he felt his own saliva covering his face. He rose from his kneeling position and placed his cock between her tits. She knew enough to cup her tits and squeeze his manhood between them. His hips began gyrating and her was titty fucking her. He pushed his balls into her chest time and time again until they were both ready to explode.
“Carry me to the bed. I want you to fuck me,” she sneared.
James picked her up in a swoop and delivered her to the bed.
James couldn’t help himself. He tore her summer dress of her lower half. She had a beautiful brown bush. It was about an inch thick and he saw her red clit swollen and popping out from her pubic hair. She laid back in her bed and he pulled her knees apart. He stuck his tongue out and slowly moved his face into her crotch. She watched him with anticipation as the tip of his young tongue moved closer to her clitoris. She closed her eyes when he got within an inch and as his tongue touched her clit, she felt her entire abdomen tighten with pleasure. He continued to flick her swollen clit with his tongue until her hips began to buck on their own. He reached up and pulled her legs apart further. Her pussy spread with ease and he saw a trickle of womanly wetness trickle down towards the back of her ass. He ran his tongue through the folds in her pussy and up until he reached her now red hot clit. She shouted with pleasure and arched her back splaying her vagina widely for him. He pressed his face against her widened pussy. Her juices were running at a maddening rate. He loved how his face became slippery with her wetness.
James reached up and began massaging her clitoris and his thumb slipped inside her with ease. In fact, he didn’t realize he was inside her until he looked down. Her insides were even warmer than her pussy lips.
James murmured, “Oh my God,” under his breath causing Jocelyn to widen her smile.
“I just can’t wait anymore hunny,” James whispered in her ear.
“Please go easily James – I’ve never done it before,” she said coyly.
“Really?” James queried.
“I thought you were joking.”
“No I am really a virgin. Make love to me James.”
Jocelyn reached up and pulled her knees back towards her meaty breasts.
James assumed a mounting position. The tip of his cock was so swollen it hurt him. Pre-cum had been dribbling down his shaft and dripped off the base of his sac. He braced her hips with his hands and moved his straight-as-an-arrow prick to her opening. The mattress was soiled with a huge wet stain already. He lined his cock up carefully and pushed forward slowly with his athletic hips. Her vagina gently parted as he entered. He felt his penis stop for a moment. He pressed a little bit harder and felt a resistance. He had never had intercourse with a virgin.
“Keep going my dear. Keep going. Keep going.” she begged.
He held her ass cheeks and pushed harder.
“Ohhhhh Yesssssssssss!” she screamed in half pain and half ecstasy.
James was shocked to see a gentle trickle of blood spouting from her opening. The mattress quickly began bleaching red. James was slightly unnerved to see his cock covered in blood when he detracted it from its place.
“Keep going – fuck me James – pleaseee.”
He drove his penis back inside her to the hilt and felt her hips buck violently towards him. Jocelyn stopped suddenly and coiled her body slightly only to let out an enormously loud moan.
“Oh my Godddddd!” she cried.
“I’m cumming!!!!!!”
After she came it only took a few minutes for James to erupt. He squirted what seemed to be a half-pint of sperm inside her warm opening. Her body seemed like it could continue to receive his surges of cum.

Part 3
 

CLIENT: Darren

James hit the showers after a great workout at the campus gym. He thought he was the only person in the shower but he heard a locker door shut. As he peered around the corner, a lean and slightly muscular guy entered the shower area. He glanced nervously at James then removed his towel from his hip. James couldn’t help but look at his cock. It was long and thin with a helmet-shaped head. Both guys resumed taking their showers.
“Good workout bud?” asked the stranger.
James responded politely without looking over, “Yeah – I really worked it today.”
“My name is Darren,” he said extending his hand.
James felt a bit uncomfortable shaking a guy’s hand in a shower room but did it since there wasn’t anybody else around.
“My name is…”
Darren interrupted suddenly, “James – I know who you are.”
How do you know me?
My Aunt Jocelyn raved about you.
James felt himself inhale quickly at the name.
She said you fucked her brains out and that you have a beautiful cock.
Darren looked at James’ equipment and smiled.
Good ole’ Jocelyn didn’t lie.
I need a special favor from you James. As you have probably guessed, I am gay. However, I am a virgin and have a mad crush on a guy on the track team.
“What can I do than?” asked James.
“I am really worried about not being able to take the pain of a man’s cock in my ass. I really want this guy on the team and I know he is gay as well. He gets around according to rumors in the locker room. I don’t want to be turned away if I can’t accept his full hardness. Your cock looks to be about the same size as him,” he explained.
“Yesss,” James continued.
“I will pay you $500 to fuck my ass,” Darren said quietly.
James thought about how he could start a healthy bank account with this new side job.
“Meet me tonight at the Heaven’s Gate Hot Tubs – 10pm.”
James got out of his car outside the Heaven’s Gate at exactly 10pm and saw Darren standing by the main entrance. Darren held the door for James. The two men were escorted to their private hot tub suite. The attendant left fresh towels and invited them to help themselves to the bar. Darren fixed up a few tequila shots and they began partying. Darren stripped nude and stepped into the steaming hot tub. James took another quick shot and murmured to himself, “I can’t believe I’m doing this.” He felt very strange taking off his clothing in front of another horny guy. With each piece of clothing he felt more and more uncomfortable. Darren slipped James an envelope contacting five crisp hundred dollar bills. James smiled and the payment definitely helped him get courage to slip his bikini undies down to his ankles. Darren watched him carefully. Both men were submerged to their chests in the steamy water. The drinks began to kick in for both men. Soon Darren was sitting on James’ lap playfully. Darren began grinding on top of James’ groin. James was surprised at how fast he was getting hard given he never so much as held a man’s hand. James figured what the hell and began massaging Darren’s muscular thighs. James suddenly found himself very curious to touch Darren’s private parts so he reached around slowly. Darren arched his back towards James’ chest to allow for James to get his hand to his pubic area. James ran his hand up Darren’s thigh and felt his right testicle. He cupped it firmly and gripped the long shaft of his cock. Darren was completely shaved and James thought how strange it was to feel another man’s cock. Darren’s cock head was plump and meaty. His shaft was a bit wider than his own. Darren began moaning loudly. Just then, Darren told James, “I’m ready James. I need you to fuck my virgin ass now.”
“OK,” responded James who seemed confused at what to do next.
Darren stood and faced the side of the hot tub. He leaned forward and grabbed his jacket. Darren took out a tube of K-Y lube and handed it to James. James stood as well and squeezed a healthy wad of lube into Darren’s waiting anus. Darren leaned forward completely so his face was on the tub’s ledge. James looked at Darren’s pink opening and felt his hard-on grow even more. James squeezed a line of clear lube onto his cock and dabbed an extra drop onto the tip of his own penis. James grabbed Darren’s athletic hips and moved up close to his bare ass.
Darren said, “Now, fuck that ass good – I don’t want you to go easy either!”
That was all James needed to hear as he plowed his manhood deep into Darren’s virgin ass. It felt like beautiful silk and Darren’s hole was the perfect tightness. James thought that it felt like he was in heaven as he buried his big dick into Darren’s ass right up the balls. James began pumping into Darren as hard as he could and Darren began screaming in ecstacy. “Yes! Yes” Fucking yes!”
Suddenly, the door to the room swung open and a young hetero couple shrieked with surprise. James quickly dislodged from Darren’s ass and submerged beneath the bubbling water.
“Whoops wrong room – sorry,” the woman said with a slight smile.
“Please forgive us and go back to business,” she added.
The door shut and Darren looked at James whose face was ten shades of red by now.
“Well, you heard the lady – let’s get back to it,” said Darren tauntingly.
“I can’t believe this night,” said James.
“Me neither now finish fucking my ass. I want to feel your hot load inside me.”
James resumed his position and started slamming his ass with a completely new level of ferocity. It only took a few minutes for James to reach a crashing orgasm. He pumped his dick very deeply inside Darren’s backside and spurted his hot load for a few minutes straight. James slowly withdrew his spent dick and watched his cum trickle out of Darren’s pink opening.
“Thank you James – Thank you,” Darren whispered as he stretched backwards in the tub.