The Initiation

by Ann Douglas

Caution: This Erotica Sex Story contains strong sexual content, including Ma/Fa, Consensual, Fiction, Oral Sex, .

Desc: Erotica Sex Story: Pledging Alpha Sigma Rho was going to be the hardest thing Thomas Jackson had ever done. And in the end, one of the most fun

"All right, move it along, especially you, Jackson," Tim Nelson said as he herded the last of the pledges into the roadside bar and closed the door behind them.

The large room beyond the vestibule ahead was dimly lit and it took the eighteen-year-old freshman a few moments to adjust and take it all in. He let out a low but audible sigh of relief when he saw that the establishment was exactly what it had been advertised as.

The last two weeks had certainly been hell, Thomas Jackson thought as he surveyed his fellow pledges, but after tonight, it would be worth it. Or so he hoped.

The pledge class of Alpha Sigma Rho had originally consisted of thirty-two initiates, but over the last twelve days that number had dwindled down to himself and the nine others standing around him. The rest had been found wanting in one way or another as they failed to complete the tasks giving to them by the pledge committee. It surprised Thomas at times that he hadn't joined their number. Especially once it became apparent that Tim Nelson, who headed the pledge committee, had taken an instant dislike to him from the moment they'd met.

A dislike that had no real cause, other than the fact that his cousin, John, had been a senior in the fraternity back when Tim had been a pledge. Evidently, John had given Tim a hard time and now he felt it was his chance to return the abuse.

"Okay, gather round," the pledge master said as he drew them all into a corner of the waiting area, "cause I'm only going to explain this once."

The ten pledges and a smaller number of brothers closed tight around Nelson, who now stood back against the far wall. There was a sharp contrast between the looks on the faces of each group. Between those who knew what was coming and those who could only be a little fearful of what the harsh taskmaster had saved for last.

"All of you have proven yourself worthy so far," Tim began, the tone of his voice carrying less than a full belief in his words, "even you, Jackson." he added, unable to resist again singling him out. "But now it's time to really separate the men from the boys."

Each of the ten took a long moment to flash back on the dozen challenges that had felled so many of the other candidates. Would any of them survive what they were all sure had to be a final, near impossible task?. If they could, then they would be part of what was unquestionably the best fraternity on campus.

"All you have to do to pass the last test," Tim said, taking a long, pregnant pause in mid-sentence, "is simply get laid."

"What?" several of the pledges said almost in unison, certain that they'd heard him wrong.

The rest had heard him right, but reserved comment as they waited for the other shoe to drop. If the last two weeks had taught them nothing else, it was that with Nelson, there was always a catch to what at first seemed relatively simple.

"Of course the challenge has a few, simple rules," Tim Nelson added, confirming their fears. "There is of course a time limit, shall we saw midnight at the latest," he went on, "and of course we don't expect you to do it here on the premises, after all this is a public place and we have better things to do with our time than to haul our asses all the way down to the police station with bail money."

A few of the brothers laughed at that.

"Just down the road, about a quarter of a mile," Tim went on, "is the Lotus East Motel. We've arranged in advance for rooms that you can use, and just to make sure that you actually got there, a few of the brothers will be parked outside and keeping tabs on who goes in and with who."

Four hours to meet someone in a bar, and then have sex with them. The pledges shared a similar look among themselves. A daunting task perhaps, but not an impossible one. After all, they were all young, in good shape and reasonably good looking. On a good Friday night, that was how some of them might expect to spend it. Okay, so it was only Wednesday, but it couldn't be that much harder, could it?

Thomas was sure that there had to be something else, a hidden catch of some sort. Nelson had made him that paranoid. Based on what the older student had come up so far, the initiate wouldn't have put it pass him to have taken them all to a gay bar or something.

That reality of that thought wasn't that far from the truth as Nelson's original idea had been to take them a few miles further down the turnpike to the Pink Pelican, a notorious hangout for lesbian bikers. It was only the intervention of the other committee members that changed the venue, insisting that if they let Tim have his way, they might just wind up with no new members this year. The final challenge they'd come up with might be difficult, but not insurmountable.

"Okay boys," Tim said as he led them to the opening in the neck high wall that separated the vestibule from the rest of the bar, "the clock is running."

Thomas stepped into the bar with his roommate, Tyler Wayne, and was relived to see that the patrons spread out across the large tavern were exactly what one might expect. In fact, if anything, there seemed to be more women than men, which could only make their task easier. It was only when they got up to the bar that the two teens realized what was different about the crowd.

With only a few exceptions, just about everyone in the bar was twice their age. Sure there were twice as many women as men, but none of them looked to be anywhere under forty.

"I think I'm beginning to see Nelson's catch," Thomas said to Tyler.

"You think?" his blonde haired friend replied, pointing out a notice on the whiteboard on the wall that Wednesday was "Over 40's Night."

"Fuck!" Thomas said under his breath when he saw the sign.

Trying to at least look undaunted, the two teens continued up to the bar and ordered a near beer, the only legal drink they could. As they slowly sipped them, a look around the bar showed a few of their fellows already engaged in conversation with a few of the unattached women.

"Might as well go down in flames trying," Tyler said as he took a long drink from his glass, wishing it was something stronger. "I for one am not going to let Nelson win that easily."

"Me neither," Thomas agreed, draining his own glass, wishing he believed it himself.

The two split up and headed for opposite ends of the bar, each wondering if their best pick up lines might work on women old enough to be their mother.

An hour and a half later, they'd found that they certainly didn't. Only a few of the woman they approached and tried to buy drinks for actually went so far as to laugh at them, but none seemed to be interested in what they were offering. Discouraging as that was, more so was the fact that two other pledges had more success and were each seen walking out of the bar with a woman on their arms.

Thomas was watching Tyler talk to a dark-haired woman in blue over in a corner and based on the amount of time they'd been talking, it looked like his friend's luck might be changing. A conclusion proved false five minutes later when the brunette abruptly walked off.

Thomas was about to head over in Tyler's direction, thinking to compare notes and see what they might be doing wrong when someone called his name from one of the small tables. It was a woman's voice, one he didn't immediately recognize.

"Thomas, Thomas Jackson, is that you?" a short haired redhead asked as she rose from the table and walked towards the teen.

It took a few seconds for him to recognize her, after all, it had been almost three years since he'd see her, but once he did, he felt a mixture of delight and embarrassment.

"Aunt Caroline!" he said in surprise.

"My God, I thought it was you," the woman said as she leaned forward and kissed him on the cheek. "I almost didn't recognize you, you've gotten so big."

If it hadn't been for the dim light in the bar, Thomas would've doubtlessly recognized her immediately. Standing almost a half foot below his own five foot five, the slim forty-one-year-old had been married to his Uncle Ken for almost ten years, having divorced him shortly after Thomas had turned sixteen.

"What in the world are you doing here?" Caroline asked. "How is everyone back home?"

"Everyone is fine," Thomas replied almost automatically, remembering that Caroline had taken back her maiden name and moved upstate after the divorce to start a new life, "and I'm going to school over in Fredrick Falls."

"My, it is a small world, isn't it," she smiled, "I live in Lafayette, that's only about a half-hour north of Fredrick Falls."

"Yeah, I guess it is," Thomas replied, thinking this night couldn't get any worse.

"But what are you doing here?" the redhead repeated. "I'm sure there are a lot of closer and much better places to hang out over by the college?"

"Well, I'm err ... I'm pledging a fraternity and ... well..." he stuttered.

"Hell week huh," Caroline smiled.

"Something like that," he answered, wishing it had only been a week.

"Been there, done that," she softly laughed, "you wouldn't believe the things I had to do back when I was pledging my sorority."

Not sure what to answer, Thomas just smiled.

"So what do they have you doing?" she asked curiously.

Thomas let out a loud sigh. There was no way he could explain what he was doing there. Not to his Aunt.

"Oh come on," Caroline urged him, "couldn't you always come to me with anything when you were younger. That hasn't changed."

"This is kind of embarrassing," Thomas admitted, hoping she would leave it at that.

"Those are the best kind of secrets to share," she grinned.

"Oh hell, I never could keep secrets from her," Thomas admitted to himself as he then proceeded to tell her the whole truth of why he was in the bar.

"Hmm, not every original," she remarked after hearing the story. "Our pledge master might've been the original bitch from hell, but she was pretty creative I'll admit."

Thomas wanted to ask what Caroline had to do to pledge, but thought that might be crossing a line.

"So what's the problem?" the older woman asked further. "I would think a good looking young man like you would have no problem attracting women."

His silence made Caroline wonder if there was another problem.

"Thomas, you're not a virgin, are you?" she asked in a soft, quiet voice so only he could hear.

"No," he instantly answered. "It's just that I don't know how to talk to the women in here, women older than me I mean. I was just about to give it up."

"I see," Caroline mused.

A second passed, then two, as Caroline considered what advice she could give him.

"I did notice a few young men leaving a little while ago with older women, were they friends of yours?"

"Yes."

"And they were headed to that motel you told me about, the one up the road?"

Again he answered yes.

"Well, I guess the answer to your problem is pretty simple," she said, a broad smile filling her face.

The look on Thomas's face said he didn't understand.

"Well, since you've decided to give up the chase, you and I could sit down at a table and catch up," Caroline said. "Or, if you really want to turn the tables on this prick of a pledge master, we could go up to that motel and have our chat there. Once that door closes behind us, no one has to know what did or didn't happen."

The suggestion took Thomas by surprise. His first reaction was that doing what his aunt had suggested would be dishonest to say the least. Then he balanced that against how badly he wanted to get in to Alpha Sigma Rho.

"Wouldn't someone see you leave with me?" he asked, worrying about what anyone she knew at the bar might think.

"It's nice of you to consider that," Caroline replied, "but aside from Mia, that's the friend I was sitting with, no one in this place knows me. We were just on our way home from a business meeting when we decided to stop for a drink."

"Oh."

"So, do you want to turn the tables on Nelson or what?"

"I guess so."

"That's the right decision, trust me," Caroline assured him. "Just let me tell Mia that I'm going and we'll be off."

Thomas watched as Caroline went back to her table and talked for a few minutes with the long haired blonde that had been sitting there. About the same age as Caroline, Mia looked past her for a long moment and right at him. Then she smiled and assured Caroline that she'd have no problem getting a ride home.

Wrapping her sweater around her shoulders, Caroline walked back to Thomas and asked if he ready to go. He wondered for a moment if he should tell Tyler that he was leaving, but then decided against that when he spotted his friend talking to someone. Hopefully, he'd have more luck this time.

As they headed for the door, Caroline asked Thomas to point Nelson out to her and she made sure the pledge master saw the two of them leave together. Before they were out the door, she heard the college senior let out a loud exclamation of surprise. Evidently, in his opinion, none of the other pledges has scored a woman that looked as good as her.


It only took five minutes to drive up to the Lotus East and step into the management office. As he had been told, the pledge committee had already worked out an arrangement with the motel owner to set aside ten rooms. Even if they went unused, the pledges were obligated to pay for them.

As he handed Thomas the key, the man behind the counter was pretty blatant about the once over he gave Caroline. With rooms that rented by the hour, there was little secret as to why anyone was checking into the Lotus East. From the smirk on his face when he was done, it was obvious she met with his approval.

"Not much, is it..." Caroline said as Thomas closed the door of their room behind them.

Looking about the small room, he had to agree. A bed and a small television on top of a six drawer dresser were all the furnishings the room held. And given the amount of time most people rented the room for, it was doubtful the dresser had ever served as anything but a TV stand. His college dorm was more hospitable.

"Well, we'll only be here an hour or so," Caroline said as she carefully laid her bag and sweater on the edge of the dresser.

"I really appreciate this, Aunt Caroline," Thomas said.

"I'm glad to do it," she smiled back at him, "I always liked you and whatever happened between me and your uncle hasn't changed that. And lets have no more of this Aunt Caroline nonsense, you're more than old enough to just call me by my first name."

"What did happen between the two of you?" Thomas found himself asking. "No one in the family ever seemed to want to talk about it."

"They never said anything?" Caroline asked in turn, a touch of surprise in her voice.

"Well they said that Uncle Ken had some drinking problems and that you couldn't deal with it," Thomas replied.

"I couldn't deal with it," she repeated. "Is that what they said?"

Thomas nodded.

"Okay, I usually take the attitude of letting sleeping dogs lie, but I wouldn't want you to think that I had simply walked out on him simply because he had a few too many drinks now and then," the redhead said as she sat down on the edge of the bed.

Thomas followed suite, sitting on the opposite edge.

"I could deal with your uncle's drinking," she said, "Lord knows there were times when both of us could tie one on. What I finally couldn't deal with was the fact that when he drank he also found it impossible to keep his dick in his pants."

That Caroline would use such a graphic phrase surprised Thomas more than the admission of his uncle's failings.

"The day I walked in on him and Sylvia Norris, you remember her don't you, she worked in Peterson's Diner, well that wasn't the first time I'd found another woman in my bed."

A quick memory of Sylvia Norris appeared in Thomas's mind. He remembered her as a thirty-something bleached blonde with a set of knockers that brought good sized tips from even the teenagers who always wanted to sit at her tables when they stopped by the diner for a snack.

"There comes a time when you have to say, enough is enough and that was it," Caroline finished. "I just wanted you to know that."

Thomas smiled and nodded his head, thinking he was glad to finally know what really happened.

"You know, Mia and I never really got a chance to have any dinner," Caroline said, changing the subject. "You think we'd get away with having you run down the block and get us a couple of burgers from Burger Barn?"

"I guess so," he answered, checking his watch and seeing they'd only been there ten minutes. "As long as we stay here a while after I come back, to make them think, well you know."

"Yes, I know," Caroline smiled. "That's not a problem, as long as I get something to eat. In fact, we could even spend the night here and really given them something to talk about."

"That would be great," Thomas thought, not wanting to actually say it because he was sure it would come out wrong. Instead, he just asked Caroline what she wanted from Burger Barn.

"Just a couple of regular cheeseburgers and a diet coke would be fine," she said as she got up off the bed and reached for her purse.

"No, I'll get it," Thomas said, thinking it was the least he could do.

"Okay," Caroline agreed. "You know, I could also use a shower, Mia and I were on the Road almost all day. Might as well take advantage of what we have here while you're gone."

Thomas watched as she took off her shoes, lifting her bare legs as she leaned on the dresser for support. Then she turned around and asked him if he would be kind enough to help her with the zipper for her dress.

Pulling down the zipper all the way to just above the crack of her ass, Thomas found a black lace bra against smooth white skin. Almost totally oblivious to his presence, Caroline lowered and stepped out of her dress, giving him an even better look at both the back of her bra and the matching panties. His mouth almost dropped open when she turned around, displaying a set of breasts that while not anywhere near the size of Sylvia Norris's, seemed perfect for her muscular yet lean frame. Back when he was younger, his aunt was really into long distance running, having even done a few marathons. Evidently, it was something she'd kept up.

"Oh don't tell me this embarrasses you," she laughed when she saw the look on her face. "I don't remember you being so uncomfortable when I used to sit around your family's pool in my two-piece."

"I guess it is kind of silly," he agreed, remembering that the two-piece in question had been rather daring as well.

"I'll be done by the time you get back," she said as she opened the door to the small bathroom. "I just need to wash off a little."

Stepping out into the parking lot just outside the door, Thomas spotted the car with the two members of the pledge committee that had been assigned to watch over them.

"Done already?" Carl Burke asked, his tone filled with sarcasm. "I kind of figured you for a quick-shooter."

"Just grabbing us a couple of burgers," Thomas replied, "It might be a long night."

The second Alpha Sig, Ron James, gave him a thumbs up which had the opposite effect than he intended. It made Thomas feel more bad than good. It made him feel like a fake, one that really didn't deserve to be part of the fraternity.

Coming back From Burger Barn, Thomas spotted Chris Parker coming out of one of the rooms with the woman he'd just bedded. She looked to be in her fifties and hardly the sort of conquest he'd be bragging about tomorrow. Still, at least he'd actually done it for real.

By the time he'd reached the door to his own room, Thomas had decided that as much as he wanted to be a part of Alpha Sigma Rho, he couldn't get in on a lie.

"I'm back," he called out to the empty room as he closed the door behind him, in case Caroline heard the door open and worried who it might be.

"Just in time," Caroline replied as she opened the bathroom door and stepped out, "I'm famished."

Even for her petite frame, the bath towel Caroline had wrapped around herself seemed too small. It was all she could do to keep it from coming undone and slipping off.

"Silly me had a little accident in there," she remarked as she took a large bite of her burger. "I splashed water all over my underwear and had to hang them up to dry."

"Accidents happen," Thomas agreed as he unwrapped his own meal.

As they ate, they chatted more about years past and Thomas was reminded how much of a friend his aunt had been. Things he wouldn't have imagined going to his parents for seemed to be easily explained to her.

"What ever happened to that nice little girl you had such a crush on, what was her name, Ginny Paris or something like that?" she asked.

"Ginger Paris," he corrected her, remembering at the same time how she had given him some of the best advice in getting Ginger to notice him.

"Oh that's right," Caroline said, taking a drink of soda. "I didn't want to say it at the time, but I always used to think that was the kind of name a porn star would have, not some innocent little girl. What happened to you and her?"

"Well, I guess Ginger lived up to her name then," Thomas laughed, going on to explain that by senior year, his former crush had earned a reputation as class slut.

"Did you and she ever?"

"No, we didn't," he answered. "I think I was one of the few guys in our class who didn't."

"Who was your first then?" Caroline asked curiously.

"Doris Piekarski," he answered.

"I don't think I..." Caroline started then hesitated for a moment. "Oh wait a second, that cute redhead in your math class, the one who used to tutor you."

"Yeah, that was her," he said. "We dated for a while, but then she won a scholarship to MIT."

"I see," the older woman said as she wrapped up the uneaten half of her second burger and tossed it into the waste basket. "And are you seeing anyone now?"

"No, not really," Thomas answered, the regret in his voice evident. "There never seems to be enough time, with classes and everything."

"Well you should find the time," Caroline told him, "if only for stress relief. All work and no play as they say."

Thomas rolled up his own trash and dropped it on top of Caroline's. His hesitation about using a lie to get into the fraternity returned and he told her about it.

"Well, the decision is yours of course," she said, "but I think you're being foolish."

"It's just the way I feel."

"Well, I guess you have to go with your feelings, I really can't fault you for that, can I?"

Caroline paused a moment, again readjusting her too small towel.

"Promise me this at least," she went on, "stay the night like I said before and if you still feel that way in the morning, then fine."

"I guess I could do that."

"Then again, there is another option," Caroline said unexpectedly.

Thomas looked up at her, not seeing what that could be.

"We could find a lot more interesting way to spend the rest of the night than just watching television," she said, the widest of smiles on her face.

"She can't be suggesting what I think she is, " Thomas thought, a sentiment reflected on his face.

"Yes, that's what I mean," she said in answer to that look.

"But you're my aunt!" Thomas exclaimed.

"Used to be your aunt," Caroline corrected him, "and even when I was, I was never more than a woman who was married to your uncle. We were never related by blood or anything like that."

"This is unreal," Thomas said. "Things like this don't happen in real life."

"Don't be so sure," Caroline smiled. "Let me be a little more honest for a moment, okay. I told a little white lie earlier when I said that Mia and I had stopped by that bar to just have a drink on the way back From a business meeting. Truth was, we had a little more unwinding in mind. It wasn't the first time we'd been there and it's not a hard place to find a guy also looking for someone to unwind with - no strings attached."

Thomas took a moment to take that in, admitting to himself that he'd hardly thought his aunt, or former aunt as the case was, was leading a celibate life.

"And again to be honest," she went on, "I've always thought you were really cute. Of course back when you were fifteen I'd never have done anything more than think that. I saw the way you looked at me by the pool, and I'm pretty sure that there were times you wondered what I looked like under that bathing suite. Am I Wrong?"

Thomas knew she wasn't but couldn't find the words to answer. Not when he knew that not only did he spend many nights wondering just that, he'd also masturbated to the image as well.

"So here we are," Caroline concluded, "basically, a man and a woman with both interest and opportunity. The question is, what are we going to do about it? Are we going to make you an Alpha Sig, or should we just sit and watch TV the rest of the night?"

Thomas took, what seemed to him at least, the longest time to answer that question. Then, he again looked up at Caroline, who was now standing next to the dresser.

"I don't even think the TV has cable."

Hearing the answer she wanted, Caroline reached down and gave the small towel Around her a slight tug. In response, the cheap cloth finally gave way and fell to the floor, answering the question that had so bothered Thomas on many a night.

"Wow!" Thomas gasped as he took in the sight of Caroline's naked body.

Having seen her in the before mentioned swimsuit many times before, Thomas's eyes immediately focused on those parts of her that suit had hidden. Small, well rounded breasts stood firm, capped by silver dollar sized areola and nipples that stood out almost a quarter inch. Down between her legs, he noted, rested a tightly trimmed patch of hair that attested that she was indeed a natural redhead.

"I hope the reality isn't too disappointing," Caroline offered in reference to all the times he had imagined her, turning slowly to give him an even better look at her.

Again not able to find the words, all Thomas could think was that his uncle has been the biggest of fools to run around when he had this waiting at home.

"Nervous?" Caroline asked, taking his silence for just that.

"A little," Thomas admitted, thinking it surprising that he hadn't realized that before. After all, here he was in a run down motel room with a naked woman who, after all, had once been his aunt - even if it had only been by marriage.

"Why don't you just lie back on the bed and try to relax then," Caroline suggested as she moved closer to him.

She paused as Thomas did just that, stretching out on top of the sheets, his head coming to rest against the pillows. Caroline gave him another moment to get comfortable, then stretched out next to him.

Sharing the pillows, Caroline leaned closer and brought her lips to his. Their kiss was hardly the sort Thomas remembered her giving when she'd used to visit his house. If she'd ever pushed her tongue deep into his mouth, as she was doing now, he was sure he'd have remembered it.

They continued to kiss for a few minutes, even as she took his hands and guided them to her breasts, letting him massage them. His movements were still awkward, a sure sign that he was still more nervous than he wanted to admit. Well, Caroline knew what to do about that.

"Just relax," she whispered as she kissed him once more, even as her hand ran down across his chest, past his belt which she quickly undid, and then ever so slowly, unzipped his pants.

"Oooooo," Thomas moaned softly as he felt Caroline's fingers brush against the naked flesh of his cock. A cry that grew even louder as she took a firmer hand and pulled it free.

"Oh my," Caroline practically purred as she slowly pumped the erect organ, "it seems that big cocks must run in your family."

Thomas knew that his cock really wasn't that big, at least not any larger than any of his friends. Still, it was nice to hear her say something like that. Especially since, his boasts to the contrary, she was only the fifth girl who had ever seen it, much less touched it.

Caroline took her time just running her fingers up and down his cock, gently pumping it each time she got to the base. Once she was satisfied with its hardness, she proceeded to disperse what ever nervousness he might have still felt.

If the touch of her hand against his cock was delightful, the wet embrace of her mouth as she took him inside it was heaven itself. Thomas had his first blow job back in his junior year of high school, from a girl willing to go down on a guy if he so much as just bought her a pizza and a coke. Doris, he remembered, had also been quite willing to give them, preferring to keep him happy with oral sex until they'd finally consummated their relationship the night of the prom. But neither of those girls had caused him to feel the awesome sensations that now filled his body. Nor had they brought him to the brink of climax as quickly as Caroline.

With practiced skill, the older woman ran her tongue over every inch of his young manhood, satisfying both the craving that had brought her and Mia to the bar in the first place, as well as a curiosity that dated back several years. In and out Thomas's cock disappeared, sliding between her lips and disappearing deep down her throat. Her fingers massaged his balls as her mouth continued to play his organ like a prized musical instrument. In less than three minutes, a familiar sensation filled her former nephew.

"I'm going to come!" Thomas gasped in warning, thinking it was already too late and that he had no control over what was happening.

In the few seconds before he exploded, he was sure she hadn't heard because Caroline made no effort to disengage herself as Doris always did. In fact, if anything, the redhead seemed to be even more into it than before, her short hair tossing back and forth as her head bobbed even faster.

Such thoughts, however, were hard to focus on as, the press of her hand suddenly gone, Thomas felt his balls explode, sending more than a week's worth of built up tension deep down Caroline's throat. A second, then a third burst of whiteness erupted from deep inside him, each eagerly swallowed up by the woman bent over him.

"Oh fuck!" Thomas gasped long seconds later when he finally regained control of himself and looked down at Caroline, scattered drops of white splashed across her face. "Caroline, I'm so sorry, I..."

His apology paused in mid-sentence as, much to his surprise, Caroline wiped away the sticky whiteness with her fingers and then licked them clean. A satisfied smile filled her face as she pulled herself up closer to him, shifting her body on the bed.

"You were saying something?" she asked.

"Forget it," Thomas answered, "I don't think it matters anymore."

"Good," she replied, "and I take it you're not so nervous anymore, right?"

"No, I mean, yes," he said. "No, I'm not nervous anymore."

"Great," she laughed as she sat herself up, "then why don't we get you out of those clothes, I'm beginning to feel a little self-conscious being the only one naked."

Thomas had barely sat up when Caroline took hold of his shirt and pulled it up and over his head. Fingers outstretched, she ran her hands down his smooth, hairless chest, pausing at his nipples just long enough to tweak each of them. From there, it was only a short trip to his already open pants, which slid off just as easily. Socks and underwear followed.

"Wow!" Caroline whistled as she looked down at his nude form, "it's a good thing I didn't know you looked this good back when you were sixteen, otherwise I might've gotten myself in major trouble."

Both of them laughed, but underneath, each wondered for a moment that might indeed have happened back then if one of them had made a move on the other. The thought then faded under the reality of what was happening now.

Slipping his hand behind her head, Thomas pulled her closer and kissed her as hard as he could. Their lips locked together, Caroline pressed him down on the bed, her body coming to rest on top of his.

Their tongues continued to intertwine as Caroline rubbed her breasts against Thomas's chest. Slipping her legs so that his left leg was between both of hers, she moved her body back and forth so that his leg pressed against and massaged her already moist mound. It didn't take much of that to bring his cock back to a semi-erect state.

Still, as much as she wanted to fuck her former nephew, Caroline wasn't in a great rush to do so. She didn't want this to be just a quick fuck, there had been too many of those since she'd tossed Ken Jackson from her bed for good. No, she wanted to give Thomas a night that he'd remember for the rest of his life. For now, at least, she was content to let him continue to explore her body.

No sooner had the two of them settled into a side by side position when Thomas leaned over and ran his tongue over the extended nipple of her left breast. He twirled it back and forth a few times, pleased when a soft purr of appreciation slipped from Caroline's lips.

Again he moved his mouth over her breast, this time taking her hardness deep inside, his hand strongly massaging the soft flesh around it. Then, kissing his away across the small valley between her mounds, he repeated his actions on her other breast.

"Hmmm, you do that very well," Caroline smiled as she closed her eyes and enjoyed his attentions. "You must've had a lot of practice."

"Actually, no," Thomas admitted, surprising himself because that was something he normally never did. "I'm really just doing what I think you would like."

"Well your instincts are right on the money, honey," Caroline replied as she opened her eyes. "You just keep on doing what you think I might like, I'll let you know it if I don't."

The smile on Thomas's face grew even brighter as he returned to her breasts and began to play with them some more. Caroline was tempted to tell him some of the other things she liked but then decided it was better for him to go at his own pace. After all, it was possible that he might find some of the things she liked rather shocking.

Finishing with her breasts, at least for now, Thomas began to kiss and lick his way down her left side. She turned her body toward him to give him easier access, guiding him to the cheeks of her ass. With great passion, he covered the rounded flesh with kisses, working his way between her cheeks and slipping his tongue up against the tight hole. Lubricating it with his tongue and pulling it open with both hands against her cheeks he pressed the tip inside her, producing a loud moan of delight.

A moan he reacted to by doubling his efforts. Caroline had the impression that this was the first time he'd ever licked a woman in that area but that it might've been something that he had wanted to try but was afraid to suggest with girls his own age. If that was indeed the case, she hoped her loud cries of approval encouraged him to try anything else he wanted.

From deep within her cheeks, Thomas worked his way around to the red haired bush between her legs. Tiny droplets of moisture reflected in the overhead lighting, samples of the satisfaction he'd already produced in her. Caroline lifted and spread her legs even further to both give him a better view and let him move his upper body between. Starting at her outer thigh, Thomas kissed his way to the center of her mound.

Lifting her head high against the propped up pillows, Caroline watched as the eighteen-year-old ran his tongue up and down the length of her pussy, sending small waves of pleasure radiating outward. Adding his fingers to the mix, and showing a lot more confidence than he had before, convinced her that this was something he'd done before. In no time at all, those small waves had escalated into powerful breakers that rippled across her body. Whoever had taught him how to lick a pussy certainly deserved a thank you note to say the least.

"Oh yeah, baby, that's good," Caroline encouraged him, "that's really good."

Reaching down, she ran her fingers through his dark hair, trying to unobtrusively guide him to her most sensitive spots. To her delight, he took the help and doubled the pleasures she enjoyed. So much so that she finally left him on his own and just let her head drop back, her eyes again closing as she let wave after wave of ecstasy wash over her.

Not able to see the clock on the wall from where she lay, Caroline could only guess at how long Thomas had been between her legs. Still, she was sure it was a lot longer than most men spent there, his uncle included. If he'd already learned that lesson on his own, he was going to make a lot of other women happy in the future. For now, however, it was time to make this woman even happier. And bring Thomas along for the ride too.

Gently getting his attention, she changed their positions so that she was now the one between his legs. In one quick motion, she slid his cock into her mouth and gripped the base with her hand. It didn't take long at all to bring it back to full hardness.

With deep, long strokes, she took him all the way into her throat in a way she was sure none of his teenage girlfriends had been capable of doing. Soft moans of delight filled her ears as she cupped his balls and went all the way down on him a third time. Following her example of before, Thomas took hold of her head and played with the locks of her hair. There wasn't anything he could teach her about the art of cocksucking, but it was a fun thing to do in any event.

Caroline deep throated him a few more times, then let his cock slip from her mouth, but not her hand. With a broad grin on her face, she looked up at him and said, "Hey big boy, wanna fuck?"

The question took Thomas off guard, until he realized it was meant to be rhetorical and funny. His only answer was a smile as Caroline, still holding onto his cock, climbed up on top of him until the tip of his manhood was pointed right between her legs.

Slowly lowering herself, she slipped his hardness deep within her, engulfing him fully. Thomas let out a loud gasp as he felt her wetness wrap around him, an excitement filled him with the thought that she was going to fuck him, and not the other way around. The few girls he had actually fucked before had simply been content to just lie there with there legs open and let him do the work. It had been fun, but had left him with the thought that it could've been even more.

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Story tagged with:
Ma/Fa / Consensual / Fiction / Oral Sex /