They Called Her Teaser Jeans

Teresa Jean was her name and she lived in a small town where everyone seemed to know everyone. It was also her hometown when she was growing up. She was twenty when she married and moved away. She had returned eight years ago after her divorce.

A mother of two with three grandchildren, the forty-six year old divorcee with hazel eyes and the sweet innocent smile was an attractive middle aged woman. When she returned to her home town, Teresa Jean became the hot MILF to the single men.

Many of the men had known Teresa Jean in high school. She was the cute skinny girl that no one gave much attention. Her long dark brown hair from her younger days is now frosted and is cut to a bob length.

Time and motherhood have been good to Teresa Jean in her development. She has firm breasts and wears a thirty-six inch B cup bra. Her derriere is wide but not fat and protrudes out nicely in back. With her thick chunky thighs, her butt has a nice heart shaped appearance.

It's Teresa Jean's butt and thighs that men really like. She is well aware that men enjoy looking at her shapely tush and she often dresses in tight pants or leggings that accentuate her big bottom. She knows how to strut in a manner that draws attention to her butt. Teresa likes the attention she gets.

Despite their interest in her by many men, Teresa Jean has gone on very few dates in the eight years since her divorce. She flirts excessively and often uses her charm to get things she needs or wants.

Whenever Teresa needs a repair done in her home or to her car, she can always find a willing man to help her. They never charge her for the work they perform but sometimes hope there might be some form of payment waiting for them.

Teresa will occasionally cook a nice dinner for her handyman and usually dresses provocatively for the event. After an evening of flirtation her friend at best gets a thank you and a good night kiss.

None of the men have expectations of being paid by Teresa with some form of sexual pleasure but her actions often led them to believe they may. It wasn't a surprise that after each had been disappointed more than once the men gave her the nickname Teaser Jeans.

In the small town where Teresa lives her male friends know each other well. Many of them play in the same softball league. They often are out together at a local bar for beers.

As each of the men became increasingly frustrated by Teresa, their discussions frequently included their latest episode with her. Many of them had already decided to no longer assist with her many repair needs without charging her appropriately for their labor.

The joke among them would usually begin as to what the appropriate charge would be. Each of the men commented on the type of payment they desired. Most had the same common idea and the consensus among them was generally the same.

"I'd have her suck my cock."

"She could bend over and beg for me to fuck her big ass."

"Teaser Jeans needs each of her hot slut holes filled with a cock and lots of cum."

One night when the guys were out drinking, Derrick relayed the story of his most recent Teaser Jeans experience. He was one of the few that was still doing work for Teresa.

Derrick was a qualified electrician. He had done some work for Teresa on his own time that his company would have charged over five hundred dollars. When he received his usual payment of dinner from Teresa, he did convince her to also go on a date with him.

After dinner at an upscale restaurant, Derrick and Teresa went to a bar for drinks and dancing. They had an enjoyable evening together.

Teresa danced seductively, often grinding with Derrick. She did not hold back in getting his hopes up. When the evening came to an end, Derrick received the usual good night kiss. Nothing more.

"That's the last time I do anything for that prick teasing slut. I can't believe how much she led me on. I thought I was finally going to score with her and she ended up leaving me with my cock hard."

His friends weren't sympathetic over the situation.

"You should know better by now Derrick. Just fucking quit patronizing her. Maybe she'll figure it out that we're not here just to serve her."

As the men were leaving the bar Derrick noticed one of Teresa's close friends was there. He stayed a while longer to talk with her, hoping that Erica could give him some insight as to why Teresa acted in the way she did.

Derrick got Erica away from her friends to talk privately. He bought her a drink and quickly turned the conversation to Teresa.

"You know I think Teresa is really hot. We've always been great friends but that's about as far as it gets. She seems to like me but I can't get anything started with her? She seems to be nothing but a tease."

Erica listened as Derrick went on.

"There's lots of other guys around town that feel the same way. She acts interested but then resists when any guy approaches her for more than friendship. I don't know, maybe she just doesn't like guys. She's not a lesbian is she?"

Erica laughed at Derrick's suggestion.

"Oh god no, she's far from being a lesbian. Teresa definitely likes men, a lot. She's always talking about how hot some guy is and I know she's not putting on an act."

"I'm not sure why she resists getting in a relationship again. I know she had a rough divorce. Her husband cheated on her with one of her friends. Maybe it's just going to take time."

Derrick shook his head and shrugged.

"Yea, that's too bad. I think it's been six or eight years since she got divorced. How long does she need? She's such a good looking woman."

"Well don't give up on her. I'd like to see Teresa find a guy who can make her happy. She has mentioned you when she talks about hot guys. I remember one time specifically after you two had a night in the hot tub."

Derrick has a hot tub at his house. There have been times when Teresa joined him in using it. They usually make plans in advance but sometimes it's a spur of the moment decision.

Teresa also plays in a softball league and occasionally her games are on the same night as Derrick's. It was on those nights when they had not made prior plans that they sometimes ended up in the hot tub with no swimsuits.

There had never been any contact between them and nothing sexual ever happened. Teresa and Derrick would always cover themselves with a towel as they got in and out.

Derrick prodded Erica to tell him what Teresa had said.

"So what made Teresa say something about me after one of our hot tub nights?"

"Oh my god, I should not have brought that up. That really just slipped out."

Erica was hesitant but Derrick was persistent to know what was said.

"Well on one of those nights she saw you with an erection."

Derrick was a little embarrassed and surprised. Erica was blushing as she thought of the best way to proceed.

"God I'm so embarrassed but since I mentioned it, I guess you have a right to know. Teresa had told me that one time when you got out of the hot tub she accidentally saw you had a hard-on."

"What? You've got to be kidding me? How?"

"Yea and her exact words were, he looked really sexy. His cock was so big and thick."

"No way she said that, you are bullshitting me now Erica."

"Seriously Derrick, that's exactly what she said. She told me she had to resist attacking you because she's always wondered what it would feel like to have a cock that big in her pussy."

Derrick was nearly speechless at hearing Teresa had not only seen his cock but would have liked to have it in her pussy. He shook his head in disbelief.

"Holy shit, what is wrong with that woman? I would have gladly fucked her if she wanted my cock. I'd fuck her anytime."

"Well maybe you should give her another chance since you know she has an interest. Get her over to your house again for some naked hot tub activity. Get a few drinks in her then find a way for her to see your hard cock."

Erica smiled at Derrick.

"She probably won't be able to resist it again."

With Erica being so open and talkative, Derrick ordered another round of drinks to keep the conversation going. Most of it was about Teresa's avoidance of relationships and how she led men on to get favors from them.

Erica agreed that Teresa was a flirt and a tease.

In a joking manner Derek brought up Teresa's sexual activity or rather lack of it.

"So she hasn't been in an actual relationship for eight years now? I'm not sure how a forty-six year old woman goes without sex for that long? She must either be horny as hell or she has a lot of toys."

With the amount of alcohol Erica had consumed she was completely uninhibited in the things she was telling Derrick.

"I don't know but maybe both. I know she has some wild fantasies but I really can't say anything about that."

"Come on Erica, you can't make a comment like that then leave me hanging. With everything else that you've told me you may as well tell me about that too."

After a few minutes of Derrick badgering her, Erica gave in.

"God, I can't believe I'm going to tell you this. Teresa would absolutely kill me if she knew."

Erica and Teresa had been out together one night. After several drinks their conversation had turned to sex. They talked about things each had tried and things they had fantasies of doing.

After Erica divulged her wildest fantasy she asked Teresa about hers. She was surprised by Teresa's response.

"Oh my god Erica, my wildest fantasy would be having sex with multiple guys at the same time. Two would be fun but three or more would be the best."

Derrick was also shocked by what he was hearing. He was happy to let Erica continue.

"My god Derrick, you would not believe how much she blushed but the excitement in her voice was obvious. It sounded like something she had thought about a lot and really wanted to experience. I only told Teresa what my fantasy was. She went into a descriptive detail of hers."

Derrick asked about the details and Erica quoted Teresa.

"I know it probably sounds really slutty but can you imagine how wonderful it would be to have one hard cock after another in your pussy. It would keep the pleasure going on for who knows how long. I'm sure I would cum over and over."

Teresa also added that in her fantasy she's tied or restrained.

"I would be totally helpless and the guys would use me however they wanted for as long as they wanted. I even fantasize that they fuck my ass. I've never had that done but I get really turned on when I think about it."

Derrick was stunned.

"Wow, that is one wild fantasy for sure. Was there anything else?"

"Oh my god yes. Teresa seemed so excited telling me about it that she didn't leave out any details."

"Well don't leave me hanging either. Tell me everything."

"Apparently Teresa has never let a man finish in her mouth. In her fantasy she's not only tied but her mouth is held open by a ring gag. She's helpless to stop the men from fucking her mouth and making her swallow their cum."

"I'm just amazed. I never would imagine Teresa having fantasies like that."

"Yea, I was shocked too."

Derrick got quiet for a moment as he took in everything Erica had told him.

"So maybe I should try to make that fantasy come true for her."

"I don't know Derrick? For now you should probably just concentrate on the hot tub and getting your own cock between her legs."

Despite Erica's suggestion Derrick couldn't get the fantasy out of his head. There was nothing he would enjoy more than being involved with some of his friends in using Teaser Jeans pussy, mouth, and ass for a night of pleasure.

Over the next few weeks Derrick continuously thought about getting Teresa to his house and in the vulnerable helpless state she had described in her fantasy. Despite having no specific plan he purchased wrist cuffs and a ring gag at a local sex toy store with the hope of using them on Teresa.

Derrick told a number of his buddies about Teresa's fantasy and how he was working on a plan to make it happen. It was no surprise they were interested in being involved. Each of his friends wanted to have their cocks pleasured by Teaser Jeans.

Six weeks after Derrick's conversation with Erica it appeared he might get the opportunity he was waiting for. At the last minute Teresa had something come up that ended any hope for that given night.

Two more weeks passed and a better opportunity presented itself. A co-ed softball tournament that both Derrick and Teresa were playing in was on the upcoming Saturday.

Derrick was certain that everyone would go to the bar after the games as they usually did. He knew it could be the perfect time to ask Teresa to his house to relax in the hot tub. The previous times they ended up naked in the hot tub had started in a similar manner.

Although Derrick was confident this time would be the same, he still didn't know how he could get Teresa in a helpless and vulnerable state. For the time being he planned to play it by ear if the opportunity arose.

On that Saturday everything progressed as Derrick had hoped. Teresa went to the bar after the games were over and Derrick reminded his buddies of his intentions.

"Be ready later. I'm hoping to get Teaser Jeans tied up and in the mood for some cock."

After a couple hours of drinking Derrick approached Teresa.

"Hey, what do you think about getting out of here and sitting in the hot tub for a while?"

"Sounds good to me. I'm ready to go whenever you are."

When they finished their drinks Derrick smiled and nodded to his buddies as he and Teresa walked out. Things were going as planned and his friends would now wait for a text message inviting them to join Derrick and Teresa.

After arriving at his house Derrick mixed some drinks while Teresa stripped and got in the hot tub. They each had a number of drinks at the bar and even though Teresa was already feeling good, Derrick mixed her drink extra strong.

Derrick had a towel wrapped around himself as he brought the drinks out. After handing one to Teresa he stepped into the tub.

He usually keeps himself covered until he's all the way in the water. Derrick was already getting anxious. He opened his towel a moment too soon to allow Teresa a quick glimpse of his cock.

With the thought of what he was hoping to do that night Derrick was already slightly aroused. When he sat down in the tub he was certain that Teresa had seen his semi-erect cock.

As the two talked it was obvious that Teresa was feeling no inhibitions. At one time Derrick noticed she had an odd expression on her face. From the way she was sitting it also looked as if she had her hand between her legs.

Shortly after that Derrick went back inside to mix a few more drinks. He sent a text message to his buddies at the bar.

"Naked in the hot tub. I think Teaser Jeans is horny and wants cock. The plan may work. Gate is open. Join us."

Before going back outside Derrick looked out the window. He could see Teresa sitting in the hot tub with her head laid back on the edge.

He watched her for a moment. Derrick wasn't certain but it looked as if Teresa may be masturbating. His cock started getting hard. As he walked towards the hot tub he had a full erection under his towel.

Derrick was quiet as he approached the hot tub. He thought he heard Teresa sigh. When he finally made some noise she seemed startled. As Teresa quickly sat up, Derrick saw her hand move from between her legs. He felt certain that she had been pleasuring herself.

When Derrick handed the drink to Teresa his towel dropped. With his erect cock fully exposed he quickly slid into the tub.

"Whoops, sorry. That was a little embarrassing."

Teresa Jean smiled at Derrick.

"Don't worry. It's not like I've never seen a man's penis before".

Over the next few minutes Derrick apologized more than once for the towel incident. Teresa insisted that it wasn't a big deal. A few minutes later they heard Dan.

"Hey Derrick, are you back here in the tub?"

"Yea, the gate is open. Come on in."

Dan and another friend Rick entered the yard. As they walked towards the hot tub they could also see Teresa and Dan apologized.

"Oh wow I'm sorry. I didn't know Teresa was here too. We can leave if we're interrupting."

Teresa was quick to respond.

"You guys aren't interrupting. We're just soaking and enjoying some drinks. You're welcome to join us if Derrick doesn't mind."

"Nope, I don't mind. There's extra towels inside the door."

As Rick grabbed some towels Teresa commented.

"I'll just close my eyes while you guys get undressed."

It appeared that Teresa had closed her eyes but she kept them open slightly as both guys stripped. It wasn't enough to be noticed but it did allow her to get a glimpse of their cocks.

Rick had brought a twelve pack of beer. As soon as the two sat down both guys opened one. He offered one to Derrick and Teresa but they were fine with their drinks.

Dan commented to Teresa.

"I bet you never thought you'd be sitting naked in a hot tub tonight with three guys."

She laughed and agreed.

"Yea but we're all good friends. With the low light and our bodies under the water it's not a big deal."

Less than five minutes passed before Michael and Joey arrived in a similar manner as the two before them. It was pretty much the same scenario. Teresa Jean made sure to get a peek at both men's naked bodies.

Even though it was a little crowded Teresa didn't seem to be bothered by sitting naked in a hot tub with five nude men. For the next fifteen minutes or so the six of them joked and laughed but mostly talked about the softball tourney.

Derrick offered to get Teresa another drink.

"That sounds good but it'll probably be my last. If I don't start sobering up I'll be here all night."

Teresa jokingly commented when Derrick got out of the tub.

"You may want to keep a firm grip on that towel when you come back this time."

"Oh yea, I will definitely do that."

When Derrick returned with the drinks Teresa and the other four guys were talking non-stop. It was obvious that Teresa was drunk and not feeling self conscious in the least about being naked in a hot tub with the guys.

The five men were enjoying themselves as well. They especially enjoyed the occasional glimpse they would get of Teresa's nipples peeking out above the water.

Teresa Jean had been on dates with each of the men at least once over the years. There had never been any sexual contact in any manner between any of them. Other than those glimpses of her nipples, none of the guys had seen any part of her body unclothed.

As the six of them continued laughing and joking Rick added a comment.

"I have to admit this all seems pretty crazy tonight. If this were a porn movie the orgy would probably be starting about now."

When Dan agreed Teresa shook her head and laughed.

"Oh my god you guys are way too funny thinking about something like that. I don't even know how the women in those movies can have sex with more than one guy? I would feel so slutty and guilty. Wouldn't any of you feel strange in that situation?"

Almost in unison the guys said it wouldn't bother them. They all agreed if they had the chance they would be happy to give it a try.

Teresa's tone got more serious.

"So it wouldn't bother any of you to stick your cock in a pussy that was filled with another guys cum?"

Each of them laughed.

"Nope."

Teresa wasn't buying it.

"Well I don't believe any of you. I think that's just guy talk."

Rick was quick to chime in.

"Well there's one way to find out."

"You are way too funny Rick but you can stop what you're thinking. I'm not that kind of a person."

Since the subject had been brought up, Derrick wasn't going to let things go easily.

"So you've never thought about that or wondered what it would be like?"