tagFirst TimeJeffrey

Jeffrey

byWannabeboytoy©

Jeffrey Boyd was a simple university student. The young man stood at 6-foot-1, dirty blond hair, a good build and had what some would say 'a face of a model.' He was a few months into his first semester, thus far having a good year. He had a 3.8 GPA and was very happy with his job, friends and new girlfriend, Mary.

Mary seemed to be a gift from God. She had virtually everything that had been missing in all his previous girlfriends. She was a fun girl with a bubbly personality. Mary let him tease her more than any other girl he had dated. The two of them had virtually everything in common. They agreed in sports, movies, and politics and most importantly, they were both Christians and virgins. Although, they had both had oral sex on many occasions. During high school, Jeff was abstinent. But less than a year ago, he realized that abstinence was a waste of time to himself. So he decided that once he met the right girl to lose his virginity to, he would go through with it. He wanted it to be special.

One flaw to Mary may have been that while her body was really well fit, her face wasn't that cute. But Jeff had made the decision that it would be perfect with her. Jeff had never liked anyone more than Mary.

Jeff walked up to his university quad. It was an open area with many students relaxing and talking between classes. Jeffrey made his way over to his friends and there was Mary. She emerged from the group and gave him peck on the lips with a smile.

"Hey sweetie! How's your day been?" she asked with sincerity. Jeff liked that about her too. She actually cared about how he felt almost more than her own current state.

"It's been good so far, but now it's getting even better." He hinted at her being the cause.

Mary smiled and leaned in close, "Why are you so good to me?" the most common question she asked him.

"Because you're so good to me. You deserve it anyway." Jeff was actually getting tired of answering that question. It was getting far too repetitive. She held him as he held her and leaned in and kiss him hard.

"Well just so you know, I really appreciate it." She kissed him again. "I got to go to class now."

"I know."

"I know you know. It's good to see you in between classes like this. You help me get through my day." This was the extent of their relationship so far. When they weren't teasing or kissing, or the foreplay that comes after the kissing, they were complimenting each other. Jeff wondered if they were going to get through everything in the English dictionary by the end of the month.

"Ditto." He replied with a smile that was returned by Mary with another kiss. Mary returned to their group of gathered friends and retrieved her bag.

The auburn hair-colored girl kissed her boyfriend one last time before saying goodbye. "Call me later?"

"Of course."

Jeff's girl smiled and trotted of happily. Jeff started walking over to his friends. He was thankful to be out of high school, so that he avoided the immature friends who would make fun of him being too lovey-dovey with Mary. He partially sat on the bricks that were around some of the quad plants. Jeffrey was a little on the outer edge of the group.

"Hey Jeff," he turned his head, "be careful today. Rita is here." His buddy Justin made him aware.

Rita was a complication. She was before Mary, but Jeff had never gotten with her or gone out on a date. The girl had dropped out of school so that she could work more often and get more money. Jeff and Rita liked each other quite a bit at one time. They had a lot in common. The problem was that Rita had a reputation for being a slut. Though Jeff's friends called her a whore. But whenever Jeff was interested in someone, he always decided that he would be the judge. After all, it was his opinion that mattered most.

The one thing that kept Jeff the most interested in Rita were her breasts. They were a natural DD cup; bigger than Mary's and Jeff was indeed a breast-man. Mary's were nothing to complain about, a C cup. They just weren't Rita's. But Mary had Rita beat in the physically fit department. Rita had an ass and a pair of legs that were a little over the top proportionally to her boobs.

Jeffrey, much like what he was doing with Mary, didn't need his girlfriend to be a perfect model that made him salivate, he just needed her to make him happy. And Rita had the potential. The two had made it clear that they liked each other. However, one night when things were moving along and Jeff was on the verge of kissing her things went wrong. He had taken her to a party. Rita was being a little anti-social and it was getting on his nerves. Later in the party, she finally became social, but it was too social. Rita was kissing another guy with Jeff in plain view. It then became obvious to Jeff that her reputation was indeed doing her justice. He cut off their relationship that night before it ever got started.

She was not happy about it. Rita felt that what she had done was perfectly okay and that Jeff was way overreacting. But Jeff just didn't have the heart to tell her the real reason was her sluttish lifestyle, and that she wasn't the girl for him. They had an argument and she told him never to call her again which was fine with Jeff.

Back to the present, it was now around five months after that incident and Jeff figured if he saw her and unless she approached him, then he would honor her wishes and not talk to her. But his mind flashed to her breasts. They truly were magnificent. She also had a cuter face than Mary with make-up. He wished to himself that he could switch Rita's top half of her body with Mary's, then Mary would be perfect.

"Hello Jeffrey." Rita was in front of him. She said his full first name with a hint of loathing, but there was also regret and sultriness in her voice as well. Jeff turned his head around and stood up slowly as if he had somewhere to be, but he looked at his former love-interest.

Rita had her black hair pulled into a ponytail. She looked good. But more importantly was her waistline. The slut had lost a lot of weight. It was just the right amount of weight too. Her legs and ass were now directly proportional to her massive boobs. She encased her lower half with a pair of tight black stretchable pants. Heels were on her feet, which didn't make sense to Jeff, but it worked. Her jugs were only partially covered by a tight long sleeve red shirt that put a lot of focus on her cleavage. To top it all off, she wore a necklace with a fairy pendant dangling right above the valley between her tits.

"Hi Rita." Jeff said with surprise, as he looked her up and down. "You've lost weight."

"I know." She replied with her hands on her hips. It looked to Jeff as though she was pushing her tits out towards him more, trying to get him to down at them.

"How'd you do it?" he said while resisting the temptation to keep glancing at her cleavage.

"Exercise and a more balanced diet." She stated like the know-it-all she claimed to be. Rita seemed to be closer to Jeff than when the conversation started.

"Well, you look good." Jeff said honestly. That was one of his biggest problems. He couldn't help but be honest virtually all the time. The only time he lied was to make someone feel better, but even then it wasn't easy. Both Mary and Rita knew this. Little did Jeff know, but Rita was intending on using this to her advantage.

"So, I hear that you're dating Mary." Her breasts were less than an inch from his chest now. Mary and Rita knew one another, but neither was fond of the other and Jeff knew this.

"She's my girlfriend." Jeff replied with a half smile as if to say 'Ha!'

Both Jeff and Rita looked over at the rest of their mutual friends. All but two were gone and the last ones were gathering their things to go. The others must have gone to class or home. Rita stared into Jeff's eyes with a look of intent.

"You know I never would've put you two together."

"Oh really?" Jeff asked wondering if she was just trying to make him feel bad.

"She just doesn't seem like your kind of girl." She stepped into him and pushed her tits into his lower chest. Jeff was surprised by this and lightly stumbled back against the low brick wall. Rita put her hands on his arms to balance him but he just sat down. Her hands moved up to his shoulders right as he sat down in that instant. She moved in closer between his legs. "Look..." she raised the bottom of her shirt, "Since I lost weight I was finally able to get my navel pierced. What do you think?"

She brought one hand to the back of his head while the other started to make circles around her belly button and her shining silver and gold stud. Jeff was so shocked by all this that he was motionless. Rita the whore was obviously trying to seduce him, even though he had a girlfriend. But at the same time he was becoming hypnotized. Rita began moving both her hands through the back of his hair, her tight shirt stayed above her navel.

Jeff was near putty in Rita's hands. She had made the decision to seduce and bed him once she heard that he was with Mary. Then she would probably add him to her list of fuck-buddies. But she didn't think it would be this easy.

"Do you like my piercing? My navel?" she asked, expecting an honest answer.

"It's very nice." Jeff practically gulped.

"Do you think it's sexy?"

"Yes, I'd have to admit that." Jeff looked up to her, over her peaks. "What are you doing Rita?"

"Do you like my tits, Jeffrey? You look like you do."

"They're... er... not... bad." His honesty was once again getting the best of him.

"Are they better than Mary's?"

It was the make or break question. Jeff thought about it for a few seconds then realized that Mary was still his girlfriend and this was not what he really wanted.

"I gotta go." He said while jumping up and pushing her back with his body. This was a mistake since Jeff hadn't noticed that he was rock hard.

"Oh I see you do. Hmmm." She looked down at his dick and licked her lips so that he would see. Jeff began to hurry away. "Where do you think you're running off to?"

"I need to use the restroom." Jeff wished he could just go home, but he had a class in 45 minutes. He nearly scampered off, but walked as steadily as he could and adjusted his hard penis in his pants. 'That was a close one.' He thought. 'Damn she got hot! Now Rita is hotter and more voluptuous than Mary. But I can't cheat on Mary and what's more is that I'm a virgin, and I am not losing it to that whore, even if she is hot.'

Rita eyed her prey as he ran off. She knew exactly where he was going.

Jeff was serious about going to the restroom, although he didn't actually intend on using it. He needed to clear his head, maybe the sperm from his balls, but more importantly get away from Rita the whore.

He walked into what he thought was the cleanest yet most isolated bathroom on campus, so that he could have more time to himself if he needed it. Jeff opened the stall, hung his backpack on the hook and sat down on the toilet. He was still hard and he really needed to take care of it. The now sexually frustrated student undid his pants and lowered them with his boxers. Jeff Boyd had never done this outside of his home, but desperate times call for desperate situations.

Jeff wrapped his hand around his hard-on and began to pull on it. He closed his eyes and thought of his usual fantasy girls, then Mary. But then Rita's tits popped into his head and that really got him fired up. He jerked almost twice as fast as before while he pictured her bouncing up-and-down on his fuck-stick.

Suddenly the bathroom door opened. Jeff stopped what he was doing and held his breath, trying to slow down his breathing to avoid an embarrassing moment. He then heard the sound of heels on the cold, hard floor. They stopped and he could hear someone bending over to check if it was he in the stall.

"I'd recognize those shoes anywhere." Rita said. Jeff was still wearing the same shoes he had when he and Rita almost dated. "What are you doing in there, Jeffrey?"

"I should ask you the same thing. This is the men's bathroom." He still sounded out of breath.

"That may be, but I put a sign on the door that says 'Toilet leaking. Bathroom closed' on it, so that no one will disturb us."

'Dammit!' thought Jeff. 'She's always been clever. But she is not going to seduce me. And I'll stay in this stall all day if I have to.'

The door to the stall swung open nearly hitting him in the face. There stood Rita the whore, looking as voluptuous as ever.

"How'd you get the door open?"

Rita showed Jeff the side of the door and the latch that was non-existent. Jeff was so distracted that he never saw it. But then again, it was there the other day.

"I took care of this earlier today, as well as the realistic sign that I made. I've been planning this for a while." She moved closer to the exposed Jeff.

He was terrified of what they might do and didn't think to pull his pants up. "How'd you know I would come in here?"

"You think no one pays attention to what you do? I watched your every move while we liked each other. I had you figured from head-to-toe." Rita placed her legs on the sides of Jeff's; his cock was below her pant-covered pussy.

"So you think you know exactly what I'll do in this situation, huh?" Jeff asked, about to push her into the wall and run away. 'But her tits are so huge.'

"Of course I do. I was a psychology major. And I have done this enough times to even know how a virgin reacts."

"How'd you know I was a virgin?"

"Please, I told you I watched your every move. It was easy to see."

Jeff had always been proud of the fact that no one could tell if he was a virgin or not, including Mary, but so much for that.

"Rita, I don't want to do this. I am not going to do this!" he stated while still sitting with his cock out in the open and the whore above him.

"Oh but you do! I know that. And you will know it soon enough. But I don't want to make you do anything that you don't feel like doing. I just want to talk to you right now." Jeff looked at Rita with a confused, quizzical expression on his face. She then lowered her ass and backed away from him, causing the inside of his cock to rub her pants against her vagina. Then she leaned back on the wall facing him. "What I mean is, I may have dropped out of school, but it's only temporary. I intend to come back next semester and renew my major, but this time I'm going to have an edge."

"And what the hell kind of edge are you going to have?"

"I'm going to have the benefit of the experience with a patient."

"What the hell are you talking about?" this really wasn't making any sense to Jeff.

"Let's talk about Mary. Now I can see that you're already in a relaxed position so I'll get right to it. Jeffrey, tell me about Mary."

'What the hell?!?! Has she lost her mind? She couldn't actually be serious could she?' Jeff thought. Maybe he would agree to this, but not with Rita, not about Mary and certainly not in the campus bathroom with his cock out in thin air. Jeff looked at her, and then he glanced at her tits and the rest of her body. It still didn't make any sense. But he figured as long as he didn't tell her anything bad about Mary, since there wasn't, then he could humor Rita. Also, it gave him a chance to stare some more at her juicy body.

"Alright, what do you want to know, Doc?" he said with a chuckle while reaching down to pull up his pants.

"Leave them down." She ordered. "I'm the doctor and I know what's best."

Jeff thought about it for a second, and then figured whatever. He was proud of his size, 8 in. "Alright Rita. Since you seem to know me so well." He rested his hands on his knees.

"How're things with Mary?"

"They're great. Never been happier."

"Does she know that you're a virgin like she is?" she could even tell that she was one too. This surprised Jeff again because he didn't know for sure until Mary told him.

"Yes she does." This was a time when Jeff could've lied with a straight face, but thought that it was possible that Rita might know that he was lying and call him on it. So he figured, 'what the hell.'

"And are you two planning on doing anything about that?"

"No, we haven't discussed it or anything." Jeff lied. But he was cheering on the inside. That was the best, most believable lie he ever told.

"Liar! Tell me the truth!"

"That is the truth. We've only been dating for 4 months."

"I know when you're lying. And I saw you two together today. You've done more than discuss it, you two have made a decision. And judging by your happiness and eagerness to lose your virginity, I'd say she's gonna give it up to you."

"Wow Rita! I gotta hand it to you. You really know your stuff. No wonder you want to major in psychology. You've got a real knack for it. Just lay off the stalker stuff, not very good for doctor and patient relationships." Jeff waited for a reply.

"I liked your teasing better than your insults."

"Most people like jokes better than insults. That's common sense."

Now Rita knew why she had to have him. He really was smarter than she thought. Jeff was tougher to bring down than she had anticipated. And even harder was the fact that he had a girlfriend. But a girl wants what she can't have. Then she wondered if she could use his thoughts of Mary to her advantage. There was a possibility that since he had never had sex that he could have a wild side. It would explain why he was ever interested in Rita in the first place.

She walked up to him slowly as she spoke, "I remember when you would tease me. And how I would tease you." Jeff remembered it too. Although, the way she would tease would be sexually. But even then it wasn't as direct as she was being now. Rita dropped to her knees. "You have a big cock, Jeffrey. You need to put it to better use."

Rita took hold of his now harder penis and began moving her hand up and down on it. Jeff moved his hands to move hers off of him and stand up but she pushed his legs down with her elbows and slapped away at both his hands with one of hers. "Tsk, tsk. Remember, Dr. Rita knows what's best. Especially for your cock, your big, thick hard COCK..."

Rita had long fake red-painted fingernails. They curved just enough at the tip. Jeff stared at them as her fingers moved up-and-down on his foreskin. The sensation was incredible. The whore moved her hand in just the right way. She spit on his cock to slick it up and then her tempo increased.

"How far have you gone with your girlfriend, Mary?" she asked looking deep into his eyes.

"Not that far. Oh... you should stop. I can't do this to her." Jeff's head fell back and forth. He tried to think of something else. He tried to think of Mary, which worked before, but now Rita's body in his mind replaced his girlfriend's face. 'Rita's tits, they're so wonderfully massive!' he thought and looked down at them. They were still covered by her shirt as they rubbed against his thighs in her motion, but it was obvious now that she wasn't wearing a bra with her nipples threatening to poke through the red fabric.

Rita moved her head above Jeff's cock-head and let her spit ooze out of her mouth and off her tongue. It traveled down to his penis in her hands, allowing her to pick up the pace of her jerking once again. She noticed Jeff looking at her ripe melons.

"Tell me how far you've gone with Mary, Jeffrey. Tell me now."

"The farthest we've gone is... she gave... oh god... she gave me head."

"Did you cum?" Rita smiled. She knew she had him now; the whore was going to have her prize.

"No... We were interrupted. Didn't... have... time... to finish." Jeff was growing more and more in Rita's hands as she rotated between them, and he was running out of breath.

"You didn't answer my question earlier today Jeffrey. Who has better tits? Me or your precious girlfriend, Mary?" it was the make or break question again. Jeff looked at Rita, and then to her jugs. She rose up on her knees to give him a better view. They looked so good in her tight shirt. The cleavage made Jeff want to cum between the two big orbs of white flesh.

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byWannabeboytoy© 7 comments/ 158599 views/ 45 favorites

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