Darlene's Ideal Lover (Be My Bottom)
Joe was a school teacher. He taught first grade. He enjoyed teaching, and he was exactly the kind of person fit to teach kids that young. He had patience, and he had a way to get the best out of even the most unruly children.
He was single and didn't have much of a love life. He lived a quiet life at home. There was a local coffee shop that he enjoyed frequenting on the way to work, and he also enjoyed attending the occasional baseball game. Though he wasn't the most athletic man, he kept himself in reasonably good shape.
It just so happened that he was doing parent and teacher conferences when he met her. Her name was Darlene. She was an attractive brunette woman. She dressed conservatively, but she had certain assets that he couldn't help but notice. She had an impressive bust line and a beautiful smile.
They were discussing her son Devon. "And he's the most helpful student in class, " Joe explained. "He'll get done with his work and help the other students."
"That's my boy, " she smiled proudly. "He's so well behaved around the house too. Sometimes I worry. Is that normal for a boy his age?"
"Well, I find that most young boys have a lot of energy, but some of them save it for the playground. From what I've seen, he's always out there running around or climbing on the jungle gym."
"Is he getting along with the other kids, " she asked?
"From what I see, he's one of the most popular kids in his class." He paused in thought. "I don't recall him ever getting into a fight with anybody. In fact, I've seen him break up a few fights."
She smiled. "That's a relief. You know, being single and everything, I worry about him not growing up with a father."
"I can't believe you're single, " Joe was surprised he said that. This was a conference, not a time to be flirting, he thought to himself.
She smiled. "The problem is I don't have time. I keep so busy at work. I never have time to meet anybody."
"Well if you want, " the voice in Joe's head was warning him not to say what he was about to say, but he did it anyway. "Maybe you might want to have a cup of coffee with me sometime?"
"I don't know, " she had a glint in her eye. "Maybe I shouldn't be dating my son's teacher."
Joe began to blush. "Well, I wasn't saying it was a date or anything, I mean, I just thought that maybe."
She giggled flirtatiously. "Okay, what the heck. Let's have coffee sometime."
"Great, how about Jamie's Coffee House around the corner?"
"Sounds good to me." She looked in her purse for her schedule book. "Oh hey, I have free time tomorrow morning? Can we do it then?"
Joe thought maybe he should pinch himself. Things were working out perfectly. "Tomorrow it is. I'll see you then."
It was one of those nights where Joe had to take home papers to grade. He was having a hard time focusing. He couldn't help but think about Darlene. She had the most beautiful blue eyes, and that smile. "I wonder if she would consider dating me, " he caught himself thinking. "Oh, you're being foolish. A woman that pretty has better guys than you after her attention."
The morning couldn't come soon enough. Joe arrived at the coffee house to see Darlene already sitting at a table. She was wearing a nice pair of jeans and a burgundy blouse. She walked over to him. "Hi there. I was afraid you were going to stand me up."
Joe shook his head. "Not a chance. Shall we order something?"
"Absolutely. I didn't want to get anything until you showed up."
They brought their coffee to a table at the far end. Joe took a careful sip as his coffee was very hot "So, if you don't mind me asking, what do you do?"
She took a sip of her coffee, leaving a trace of her Pink Champagne lipstick on the cup. "I'm in Tech. I set up computer systems, surveillance the whole nine yards."
"That sounds interesting."
She smiled. "It keeps me busy. Of course, being a single parent means I don't have time to take some of the bigger jobs I used to. But that's okay. We do okay."
Joe took a nibble of a cookie. "I hope I'm not being too forward in asking, but what happened to Devin's father?"
Darlene paused for a moment, as if she didn't expect the question and wasn't sure what to say. "Oh, well, she, I mean, he passed away three years ago. So, I decided that I needed to be there more for him and not to take on jobs that would take me out of town. There's a couple of accounts I keep, but most of the time I go to my office job and make it back home that evening. I have a good babysitter, so it works out."
"Still, it must be difficult."
"I manage." She took another sip of coffee. "So, how do you like being a teacher? Seems to me that it could be challenging having to put up with so many children."
He shook his head. "Not at all. Children are easy. Every once in awhile, you'll get one who acts up, but they're pretty well-behaved."
"I don't know." She looked at him with a hint of admiration in her eyes. "I think one child can be a handful. You have a classroom of 20."
He Shrugged. "I like kids. Unfortunately, I don't have any of my own, but being able to teach them and help prepare them for the future is the next best thing."
They had a pleasant conversation and talked briefly about things that they like, music, entertainment. Basic small talk, but they found that they had similar interests. Before Joe knew it, he was off to work and she was off to do her thing.
When he arrived in the classroom, he realized that didn't ask her on a date. This was something he really wanted to do.
Joe went a few days without seeing Darlene. He did have her phone number, but he felt like it might be inappropriate to call her. She didn't say anything about wanting to date him, and he worried about things like sexual harassment. He had taken the sensitivity classes that were mandatory among the school staff.
He still couldn't get her out of his mind. It was five days later when he happened to run into her at the grocery store. She was dressed casually. She wore a cute red top that didn't leave a lot to the imagination and a tight pair of shorts.
Boldly, he walked over her. "Oh, hey you. Fancy meeting you here. Do you come here often?"
She laughed. "Only when I run out of food. How you doing sweetie?"
"I'm fine. How about yourself? I've been thinking about you."
"I'm okay. Just busy with work. I had a really big job offer." She frowned. "Unfortunately, I can't take it. It would be really good money too. The kind of money where Devon and I could even move to a nicer house."
"Why can't you take it?"
"It would require me to be gone for a couple of weeks out of the year, maybe more. I won't leave Devon for that lomg, even though I trust the babysitter. I swore to his... I swore that I wouldn't neglect him for work, and I intend to keep that promise."
Not really thinking about what he was doing, Joe put his hand on hers on the shopping cart. "I'm so sorry. I wish I could help."
"Anyway, I should get my stuff and go. Nice seeing you again." She moved on. Joe felt like he needed to say it now or the opportunity would get away from him. He didn't get everything that he needed, but he made sure he was in a line next to hers. They both left at about the same time.
Joe approached Darlene at her car. "I hope I'm not being too forward, but I have something I really need to tell you. It's just that..."
"Joe, don't, " she interrupted. "Please."
"Just let me say this. Darlene, I like you a lot. And I think maybe we could be good friends. Maybe more than that, but."
She frowned. "Joe, I have to tell you something, and I know you might not like it."
"You can be honest with me. I'll understand."
"It's just that I don't think you'll like it, but you need to know so you can move on with your life."
Joe was worried. "You make it sound like you don't ever want to see me again, " he remarked with a little bit of fear in his voice.
She shook her head. "No, that's not it. It's just that." She paused, very nervous about what she was about to say. "And please, can you keep what I say between you and I?"
He took her hand. "Darlene, you can tell me anything. I'm your friend. I'm not going to tell anybody."
"Joe, I'm a transsexual."
There was surprise in his eyes. "Really? Amazing. I never would have known that, you're so. You're so beautiful and I'm. I'm sorry I said that, I mean it's not like..."
She smiled. "Thank you sweetie. You really know how to make a girl feel good. But..."
"Darlene, I really don't care. I like you, and I want to see you more. And..."
"There's more. Joe, I. Well, there's a lot of transgender women who, will they don't like to."
"I told you that you can tell me anything, Darlene. Go ahead. You can trust me."
"Well, I. I have my, you know, penis. And, I like to use it and. I prefer to. I don't know how much you know the terminology, but I like to top."
"Top, " he asked confused? "Do you mean you?"
She smiled and blushed at the same time. "It means I like to use it on my partner. I. Well, my wife never had any complaints, and the couple of men that I dated, they didn't seem to mind, but I feel you should know."
Joe was intrigued at the idea, but societal conditioning won out in the moment. "Oh, " he said. "Well, thank you for telling me." He turned and walked back to his car.
Darlene watched him walk away with a hint of sadness in her eyes. She actually found Joe to be quite attractive and had hoped that he would react differently when she told him the news.
Joe had a million thoughts racing through his mind as he drove home. "She wants to fuck me? I'm not gay. No way. How would that even work?"
The thoughts didn't go away even a few days later. All he could think about was how beautiful she was and how much they had in common and how happy he felt in her presence. So, why was this a problem?
As another week went by, Joe started wondering how it would feel to be anally penetrated. He resolved to go to the adult store and get a dildo. He had to know.
Nervously, he walked into the store and in a roundabout way to the dildo section. He felt awkward standing there, so he headed to the adult DVD section and looked around for a while. There were videos with transsexual women and he noticed their penises were blacked out on the cover. They looked gorgeous.
He strolled around the store, looking until a female clerk approached him. "Can I help you?"
He blushed. "Oh, well, I'm kind of curious, I mean, I want to maybe get a, a toy."
She giggled. "A toy? Do you mean a dildo?"
He nodded.
"No need to be ashamed. This is exactly what we're here for. I think we have just what you're looking for." She led him to the dildo section and picked out a modest six inch dildo. "This one vibrates too. Do you have any lube?"
"Lube? I have Vaseline and home."
She shook her head. "No, you need something better than that. Here, " she handed him some lube from another shelf. "This will be better. You want to be nice and loose down there. It will feel better for you, trust me. I know it helped me."
He looked at her for a moment. She grinned. "Well, come on. Gay guys aren't the only ones who like anal."
He blushed. "I'm not gay. It's just this woman that I met, I mean, well I think I might have blown it with her, but."
"Relax sweetie. Here, let me ring you up. Unless there's anything else you want to get? Maybe one of those transsexual DVDs you were looking at?" She was teasing him.
"Well, I don't know, but."
"Sweetie, if you're curious, I've had a couple of guys rave about Shemale Ass Bandits 3. It has Vivian Fox in it. She's so sweet. I'd let her do me too."
He thought for a minute. "What the heck, I'll get that too."
Joe found that his heart was racing as he walked out of the store. It was like he had done something against the law, which wasn't the case. He took his lube and DVD and new toy and headed back home.
He didn't wait. He pulled the DVD out of the wrapper and put it in the player. The dildo was next. He forgot to get batteries, but he had some size C batteries laying around. Soon, the DVD was playing. There was a white guy sucking the penis of a rather attractive Brazilian transsexual woman. She had an impressive seven inch cock, and the man was going to town on it with his mouth.
The man was smooth all over his body, but Joe was not. He also had a slight tummy. Not too big, but certainly not as fit as the guy on the screen. He was fixated on her cock. "Can I suck her cock, " he wondered as he watched?
He took the dildo and started licking the head. Then he opened his mouth and started sucking on it. Soon, he was trying to take it as deep as the guy on the TV screen and he gagged. He felt embarrassed by what he had done. With a tinge of guilt, Joe put the dildo back in the bag and stopped the DVD.
It was a night when Devon was at his grandmothers. Darlene had done a job for somebody she wasn't too fond of. The pay was okay, but his wife was a bitch. She was barking out orders and generally being too demanding. But, it was one of the best paying gigs she had. Inevitably somebody would do something stupid with the computers, and she would have to come in there and fix it.
She went to the Sam's Lounge to have a few drinks that night. She felt like glamming it up just a little bit, though she knew picking up guys was a bit risky. She just wanted to go out and flirt a little bit. She wore her sexy red dress and did her makeup up in a flirty style.
Darlene needed it badly. She really wanted to take out her aggression on a nice tight ass, but she doubted she would find a willing man. As expected, guys were buying her drinks all night. There was even a couple of women flirting with her. One blonde woman in particular was practically throwing herself at her.
"You should come home with me, " the woman said.
"Really, " Darlene smiled? "Why should I do that?"
She leaned over to her and and rubbed her back. "Because you and I could have a really good time together sweetie."
"You think so?" Darlene was curious.
"I know so baby. I could lay you on the bed and stick my tongue in that sweet pussy of yours. I'd have you quivering in delight."
"Really, " Darlene said, getting an idea in her head.
"Yes really. We should go. I have alcohol at home. We can take the party back there. Get nice and intimate." She brazenly kissed Darlene.
"What if I had something else?"
"What do you mean something else," thew woman asked in confusion? "Come home with me, baby."
"What if I had a cock, sweetie? Would you be okay with me taking you to bed and fucking you like a rabbit?"
The woman stopped and looked at Darlene for a moment, trying to figure out what was being said. She looked surprised and then started to laugh. "What are you talking about?"
"I'm talking about what if I had a cock? What if I bent you over your couch the minute we got home and fucked you up the ass? Would you like that too?"
The woman laughed. "You don't have a cock. Come on. You don't." She paused for a minute. "I need to go to the little girl's room." She kissed her. "Don't you go anywhere, sweetie."
Darlene thought for a moment. The lady was attractive, and she liked the idea of taking her to the bedroom, but she doubted the woman was ready for what she had. She didn't want to cause a scene. She finished her drink and paid her tab and headed out the door.
As she walked out the door, a man noticed her and stood watching her for a moment as she walked to her car. "Darlene, " he called her.
She looked back. She squinted as she looked at the guy. It looked like Bill Anderson. Bill ran a company that ran surveillance. They traveled all over the world. They might be checking on a spouse cheating on their significant other. They might be looking into somebody who engaged in suspicious activities such as embezzlement or plotting an act of terrorism. They made really good money.
"You, " he said with a smile as he walked up. "Darlene, why won't you work for me?"
"I told you dear, I can't work for you. I can't be away from my little boy. I made a promise."
"Come on, there's good nannies out there." He looked at her. "God, I miss you. The guy we've got doing our tech right now sucks compared to you."
"Well, I am the best, " she said confidently. "But that's not why you miss me now, is it dear?"
"What? What do you mean, " he asked, knowing fully well what she meant.
"Do I have to spell it out for you, dear?"
"I'm just asking what you mean. Darlene, I need you to come out to Florida and check out a few things for me. We got this job we're getting ready to do for a guy in Switzerland. I'm telling you, it's a big deal. I can't say much, but I really need your expertise."
She smiled and nodded. "Yeah, I know. I know what you really need, but I want to hear you say it."
"Come on, Darlene."
She put the key in the door of her car. "Nice seeing you again, Bill."
"I need you to bend me over and fuck me like a little pussy boy. I need you to make me your bitch. Please, Darlene."
She smiled proudly. "There. Now, was that so hard, dear?" She kissed him. "But. I can't take your job offer, Bill. I can't leave Devon. I made a promise to his mother."
He frowned. "I know. I wish I could move you into my house. I'd give you guys a good home."
She laughed. "Yeah, and what would Helen say about that?"
"I guess I hadn't thought about that, but I'd think of something. She could take care of that monster of yours too."
She laughed. "Helen's up tight sweetie. If you told her what was going on between you and I, you'd be losing half your company right now."
"I know you're right." He looked around. "Hey, what do you say we do something crazy?"
"Like what?"
"What do you say we go off behind those bushes and I give you something to remember me by?"
Darlene laughed. "Yeah. What do you say I just bend you over the hood of my car and go to town on that tight ass of yours?"
"Darlene, everybody would see. Come on now. Let's go behind the bushes."
"Yeah, everybody would see what a little pussy boy you are. But you are one, aren't you?"
He nodded. "I am. I'm your little pussy boy. God, I can't stop thinking about you. I want to suck it."
She looked around. "Okay, behind the bushes. Let's go."
They stood behind the bushes. "Okay, get on your knees. Mama has something you've been missing."
"That monster she cock of yours, " he asked as he got on his knees?
She lifted up her dress with her little bit extra tucked between her legs still. She pulled down her red panties and removed them, handing them to him. "Here you go, sweetie, I want you to do something for me."
"What? Anything."
"Take off your pants."
"Here?"
"Right here, right now." She smiled. "Take off your pants."
He removed his pants, and the bulge in his underwear was obvious. "Now what?"
"Take off your underwear and put on those panties."
"I can't wear panties, " he complained.
"You can and you will, " she insisted. "That is if you want a taste of my sweet candy."
He removed his underwear and she stood behind him, poking him in his rear end. "When's the last time you had it?"
"The last time I was with you, " he frowned. "What's it been, three years?"
"You mean you haven't had your wife buy a strap-on yet?"
"I can't do that, " he said as he faced her. "She would never go for it."
"Reach down and grab it sweetie, grab what you want."
He reached down and took her monster she cock in his hand. He looked at her. "I want to suck it for you. And I want you to cum in my mouth."
She laughed. "Well, of course I'm going to cum in your mouth, and you're going to swallow it like a good little bitch. You always were a good little bitch, weren't you?"
"Yes, I'm a good little bitch."
"We both know why you really want me to come back there. It's not because I can fix your silly equipment. It's because my sexy equipment is just what's needed to fix you, isn't it?"
"Oh God, I missed you so much." He started sucking her cock and trying not to break eye contact. He was thinking about how it would feel inside his ass again.
"Sweetie, bring up the subject with Helen."
"What subject?"
"Don't play that game with me, " she smiled. "Talk to her about getting a strap-on and bending you over the kitchen table. All over the house. Tell her you want to be her bitch."
He shook his head. "She'd never go for it. No way in hell."
"Do yourself a favor, " she insisted. "Just ask her. Figure out a way to do it subtly, then ask her. You're begging for this, and you never know with some women."
"I'll think about it."
"Will think about it while you're sucking my cock. Submit to my superior cock."
He was on his knees with her cock in his mouth. There was a desperation in how he was doing it as he greedily sucked her. "Slow down, sweetie. Take your time. Savor this."
"God, I need you to come back and work for me again."
She laughed. "Less talking, more sucking. Come on sweetie. Show Mama that you know how she likes it."
He slowed his pace, taking care to lick her tip the way she liked it before going down deep and gagging as he tried to take as much of it in his mouth as he could. She laughed. "That's it, gag on it you little bitch. Gag on my cock."
He continued sucking. It had been a while since Darlene had anybody do this for her, and she was enjoying the experience. She was enjoying the control she had over the wealthy businessman. She also knew that he was the best client her business ever had.
He could taste her and that made him more desperate for her sexy reward. "Baby, I'm gonna cum." He hummed on her cock as he continued sucking it. "Baby, I want you to swallow it all."
She began gently thrusting as he continued sucking, and she put her hands on the sides of his head. He became her object. "Here it comes, oh God yes. Here you go baby, yeah."
She released spurt after spurt inside his eager mouth, and he greedily obeyed her command to swallow it all. He didn't stop until he was sure he had gotten it all.
She smiled. "Good boy." She looked at him. "You look cute in the panties. Why don't you go ahead and keep them to remember me by."
He picked up his pants and reached into his pocket handing her a card. "Consider my offer. I'm being serious. We could use your help."
"Yeah, I don't know if I'd be able to do it."
"Think about it, darling. You know my money is good, and you'd be able to do things for that boy of yours. Start a college fund."
She took his card.
He put on his pants. "You know, I'm in town for a couple of days since I have some important meetings. Maybe you and I can hook up before I head back?"
She grinned. "Maybe. Let's get out of here before people notice us."
Joe went through another day of teaching the children at school and brought home papers to grade. All the while, he thought about what he had done the night before and why he had done it.
He thought about Darlene. Midway through grading the papers, his curiosity got the better of him and the DVD was back in the player again. He pulled out the toy and the lube.
The scene of the man sucking on the transsexual cock soon changed. She had her mouth in the man's ass. She was getting it ready for something, and Joe knew what that was. A few minutes later, she was pushing her cock at his rear passage and was soon fucking him from behind.
Joe's mouth was wide open in amazement. Was this gay? But that was a beautiful woman who happened to have a penis fucking a guy. The lines were blurred. Joe was very turned on by what he witnessed. He pulled out his penis and begin stroking it as he watched. The man on the screen appeared to enjoy what was happening, and the woman seemed very into it.
The scene played out for quite some time as they changed positions. Sometimes, she was stroking the man's cock, as she fucked him and other times he was stroking himself. Soon, he shot his load on his own stomach while she was fucking him. Soon after, she pulled out and shot her load on his face. Joe came hard.
He was embarrassed yet again and put everything up. He went back to grading the papers, but Darlene was on his mind again. Would he let her do this to him? She was adamant that she liked doing that to men. Joe knew that being with her meant that she would do that to him. After grading the papers, he went to bed, drifting off to a dream where he and Darlene were together kissing and making out. He just couldn't get her out of his mind.
After another day of school, Joe came back to the DVD. Vivian Fox was in the next scene, and she was a fox. A flirtatious, cute blond woman with a big cock. Teasing and verbally humiliating her man as he sucked her. Joe was incredibly turned on. This time, he reached for the lube.
As the scene played out, she was making the man beg her to fuck him. And the man begged her. The word play between the two as the scene went on was amazing. Joe had fingers of lube inside his tight hole, getting it very wet. Next came the dildo, which he set on a low vibrate. It hurt trying to push it in, and he spent a few minutes trying to get over the pain before finally succeeding.
He wasn't sure how to feel. It hurt. "Could I do this with Darlene?" But he persisted. Darlene enjoyed doing this to men, but the men must have enjoyed receiving it too, right? Was there pleasure? As he continued to insert the toy deeper, he got more comfortable. The pain gave way to pleasure. The scene on the screen showed Vivian Fox and the guy very much in the throes of passion and pleasure.
Joe felt strange. Did he have to pee? Was that an orgasm building up? He didn't know, but it felt strange and good at the same time. He slowly stroked himself as he sat on his dildo watching the scene on the screen.
The scene was filmed in Brazil, and sometimes they have bareback creampie scenes. Vivian Fox was famous for giving men creampies, but Joe had no way of knowing. He had only discovered transsexual porn with this DVD. As he slowly stroked himself and felt the pleasure, he was surprised when Vivian unloaded her seed inside the willing man's ass.
Soon, Joe was cumming all over the carpet In front of him. He could not deny that he enjoyed what he had just done. Now, he had to work it out in his mind as the shame tried to build up.
There was one thing that drove him back to these thoughts. Darlene. He was attracted to her. But he liked her. He still wanted to be with her, but he didn't know if he would see her. He didn't bump into her at the grocery store. He hadn't seen her anywhere. Though he had her phone number, he resisted making the call out of concern that he might be seen as harassing her.
Joe had it bad. His life consisted of him having his morning coffee at the coffeehouse, teaching his students, grading their papers and having more fun with the toy as he got used to the pleasure it was giving him. This played out for the next couple of weeks before Darlene showed up at school to pick up Devon.
Devon was playing with his friend when he saw his mother and ran to her. Joe walked over to her. "Darlene, great to see you."
She frowned. "Is it? I didn't think you wanted to see me again."
He shook his head. "No, it's not that. Can we talk?"
She leaned down to Devon. "Sweetie, go play with Mikey for a little bit, would you?"
"Okay mommy, " he ran over to his friend.
"You have a few minutes, so make them count, " she said impatiently.
"I'm sorry Darlene, " He began. "But you have to admit that it was a shock what you told me, and I didn't know. It was still stupid, and I'm sorry."
She put her hands on her hips, trying to look upset with him, but knowing what was coming. "Yeah, so what are you trying to say?"
"I want to go on a date with you, and then we'll see where things go from there. I want to get to know you."
She grinned. "Well, you know where things are going to go, dear. You're going to take my she cock in your cute little ass. Are you man enough to take it?"
He blushed and nodded.
She shook her head. "I want to hear you say it, dear."
"You're going to fuck me, " he said, still blushing. "I want you to fuck me."
She kissed him on the cheek, grabbed his ass and whispered in his ear. "Now, was that so hard?"
"So, what now?"
"Devon goes to his grandmother's this weekend, so I'll have the house to myself. What you need to do Is get yourself ready and come over on Friday night. 22 Willow Street. I'll expect you there no later than 7. Is that understood?"
He nodded.
She grinned and kissed him on the lips. "Relax baby. You and me are going to have a lot of fun together."
Friday couldn't get there quick enough. Joe rushed home and took a long shower, also giving himself a douche, which was something he learned when he looked online a week earlier. He slipped into a pair of designer underwear, slacks and a dress shirt and headed out the door.
He arrived at her house at 6. She smiled and showed him through the door. "You're early." She kissed him on the cheek. "I like that."
"You have a nice place here, " he remarked as he looked around.
She nodded. "It is nice, but I'm still thinking about that job offer. There's a house across town that's nicer, but I have to figure out what I'm going to do with Devon. I don't want him being taken care of by some babysitter while I'm out of town working."
"You're still thinking about that job?"
She shut the door. "It's a good gig, and I like my work. But I need somebody at home I trust 100%."
"I see."
She looked at him long and hard. "Joe, I like you a lot. You're a sensitive, caring man. You have a lot of patience and are good with kids. You and I have a lot of things in common, but I have to ask you something point blank."
"Of course. Ask me anything."
"What are you looking for in a relationship, or are you looking for a relationship at all? Or, is it just sex?"
"I want a relationship, " he replied as he initiated a kiss with her for the first time. "First and foremost. But sex is nice too."
"We'll just see about that," she said with a wink and a grin.
"So, where do you want to go?"
"I got reservations for Martini's, but that's not until 7:45. Then I thought maybe we could go get a night cap. But since we're early, " she added. "I thought maybe we'd have a little fun here first."
"Oh, " he said nervously as he realized what was happening.
"Let mama see what she's working with here."
Nervously, he unbuttoned his slacks to reveal his baby blue designer underwear. She laughed. "Oh, those are cute. Did you buy those just for me?"
He nodded as he removed his dress shirt, revealing his slightly hairy chest.
She ran one of her hands over his chest. "Mama likes, " she said. She ran her hands slowly down his chest and his stomach and gently caressed his crotch. "Mama likes that too."
Darlene surprised him by getting on her knees and pulling his underwear down. Then, she took out his semi hard cock. She began licking it and kissing it. She looked up. "Just because Mama likes to top doesn't mean she doesn't like a good cock in her mouth too."
With that, she began licking and sucking his cock and Joe was surprised when she took a finger and slowly pushed it into his loosened hole. She looked up at him again. "Have you been experimenting with toys down there, sweetie?"
"Yeah, ever since you told me about yourself, I couldn't help it."
"I knew it, I knew you were a little bottom boy." She stood up. "Let me Show you something. I hope it doesn't scare you, " she grinned. She removed the skirt she was wearing, revealing a rather nice bulge in her pink panties. She removed her blouse and her pink bra, showing her nice D Cup breasts. Though they weren't completely natural, hormones grew them quite well before the best breast job her money could buy.
"So, she asked, "what do you think?"
He started licking her nipples and moved up to kiss her. "I like what I see so far."
"Well, get on your knees and see the rest, pussy boy."
He wasn't really prepared for what he was about to see. When he removed her tented pink panties, a rather intimidating eight inch cock popped out and hit him on the nose. She laughed. "Don't just stare at it sweetie. Suck it."
Joe held it in his right hand. It felt soft and yet hard. He'd never held another cock in his hand before, but he liked who this smooth shaven cock was attached to. He slowly started stroking it. "Put your mouth on it, baby. Show Mama some of your oral attention."
Joe begin licking and sucking the tip before daring to take it deeper. "Just what I thought, your a cock sucker too, " she giggled. She ran her hands through his hair. "That's okay baby. Mama likes a cock sucker."
As she got harder, she decided it was time. "Sweetie, why don't you go over there and bend over the table. Mama needs to take that tight ass of yours."
He slowly walked over to the table. "I want to tell you something, " she said as he bent over the table.
"What's that?"
"I've liked you from the moment I met you, and I think you and I would make a good couple, baby. You and me together. Do you like that idea?"
He felt her she cock pressing up against his tight hole. "Yes, I like it a lot."
She began to push in. "Good, Because I think you and me will be real good together." She pushed in further and heard him begin to moan. "Oh, God. Baby, you're so tight. Just the way Mama likes it."
She pushed in as far as she could go before letting it settle there. "Oh, God, " he moaned. "You're so big."
"Thank you, " she said with a chuckle. "You better get used to it. Mama likes to fuck. If you're a good little pussy boy, Mama might give it up for you too."
"Oh God, " he moaned as she began slowly thrusting in and out while she grabbed his hips.
"Such a nice tight ass, baby. Mama's tight ass now." She continued to slowly take him from behind. "Whose ass is this?"
"Oh, God, " he moaned. "Your ass."
She slapped his ass. "Damn right it is. You're my pussy boy now, baby."
The pain began to give way to pleasure as he loosened up and accepted everything she was giving him. He knew this was right for him.
She leaned down on him with her stiff cock still inside his rear passage. She kissed him on the neck. "Does it feel good, baby?"
"Yeah, real good."
She kissed his neck again. "It feels good to me too, sweetie."
This seductive and sensual scene played out for several minutes as she began to feel the pleasure building. Joe had one thought on his mind from the moment she entered him. The scene of Vivian Fox on the DVD. Would she?
Darlene's breathing began to get heavy as she was about ready to cum. She wasn't stopping until she tensed up, thrust in and began to unleash her seed inside of her new pussy boy's ass. "Oh yeah, oh yeah. Yeah, baby, take it."
Joe was on the verge of his own orgasm, though It didn't happen before Darlene erupted inside of him.
She leaned down on him, reached around and began stroking his cock. Her own cock still inside him. Joe couldn't hold back. After a few moments, he came on the floor.
She leaned down and kissed him on the neck. "That was incredible, " he said.
"I'm glad you liked it, " she replied. "What do you say we go clean up and get ourselves something to eat?"
They stood face-to-face kissing each other. "Sweetie, We should go before I give you a taste of round two."
Dinner at Martini's was delicious, but the conversation that Darlene and Joe were enjoying made it even better. He felt so much better in her presence that he was certain that being with her was his destiny.
They went to Skip's Lounge for a nightcap and enjoyed drinking expensive wine and chatting some more. Another couple kept playing music to dance to and were out on the dance floor by themselves.
Darlene was watching the couple and looking back at Joe. "Want to dance," she finally asked?
He shook his head. "I'm not a very good dancer."
She smiled. "That's okay, I'll lead."
He blushed. "Isn't the man supposed to lead?"
She put her hand on his. "Darling, I'm already leading in the bedroom, I don't think it's a big deal for me to lead on the dance floor."
She took his hand and led him to the dance floor where an upbeat song was playing. Joe was just trying not to make a fool out of himself, Darlene was a little bit more into it. They danced to a couple of upbeat songs before a slow song played.
Darlene held him closely. Both of them were feeling a nice buzz, and he could feel her she cock pressing against him. "I want you," she spoke deliberately into his ear. "I want you now."
"Here," he blushed. "Like, here at the bar?"
She moaned soothingly into his ear. "Oh love, you're so naive. Wouldn't it be fun if I bent you over the bar and gave you a good railing in front of everybody?"
"I don't know about that," he replied, his facial skin tone not returning to its regular shade just yet.
"No, we can go home. I figure you're going to stay at my house tonight anyways, right?"
He kissed her on the lips. "That sounds good to me."
They came home and no sooner had they shut the door than she wrapped her arms around him and gave him a passionate kiss. "We're doing this," she finally said.
He looked around the living room. "Where?"
She kissed him again. "Anywhere I want you." She thought for a moment. "I know, let's go out to the garage?"
"The garage?"
"Come on," she took him by the hand. She had a strange looking swing hanging from the ceiling, and Joe was trying to figure out what it was for. She walked him over to the swing. "I've had this for a while. I've had lovers get on the swing. It's a special kind that I had made for my lovers. It'll put you at an angle, and basically, I can make love to you while you hang from the swing."
"Oh," he blushed. "That's different."
She eyed him lustfully. "Strip, darling, now. I want you naked and on that swing."
It didn't take long before both of them were naked, and they were kissing and fondling each other next to the swing. "You're so beautiful," she said between kisses. "Where have you been on my life?"
"I'm here now," he replied as he felt her hand wrapping around both his cock and hers, slowly stroking them. He liked the friction between the two cocks in her hand. "Darlene," he said as she kissed him again.
"Yes, love." She was slowly stroking their cocks together as she looked him in the eyes.
Desperation showed in his eyes. "I want you inside of me."
She grinned. "Well, that was the idea of taking you here. Get on the swing."
"It didn't take much to get him secure on the swing, and she was kissing him while she fingered his ass. "If I didn't know better," she said between kisses, "I'd swear you were meant to be a bottom, and you'd been doing it all your life. You're a natural."
"I haven't," he nervously smiled, "but it does feel right to me."
She put a third finger into his ass. "Oh darling, you have such a sexy ass." She positioned his ass to take her beautiful she cock, teasing him as she poked at his hole, intentionally trying not to insert it.
This sensation of her poking against his hole but not entering him had him nervous. "Is everything okay," he asked?
She grinned him. "It's perfect, but you know what I want to hear, right?"
"Darlene, would you please make love to me," he pleaded, finding the romance in the moment.
There was almost a tear in her eye. He was easing into his role as her bottom lover better than she had expected. Asking her to make love to him was something different. Usually, the guy would just flat out tell her to fuck them, and here was this beautiful little man asking her to make love to him.
She leaned down and kissed him, slowly inserting her cock. "I want you to feel every inch of me sliding into you, my dear. Feel me inside of you. I want you to get used to this feeling. This is me showing my love for you, baby."
"Oh God," he moaned, biting his lower lip and looking her in the eye. "I love you too. I love you so much."
Darlene marveled at the moment. She never thought she'd find love among her sex partners, but this beautiful school teacher was just the man of her dreams. His ass wrapped nicely around her sexy shenis, and she was slowly making love to him.
The sensation of being strapped to the swing, hanging in the air, was different. It was like Joe was helpless, but he knew that he could trust her to take control. He surrendered to the moment, feeling her cock stretching his ass as they made love. She would kiss him at times.
The moment was passionate and beautiful at the same time. They maintained eye contact for most of it, her cock slowly making him feel better, and his own cock starting to leak just a little bit.
Darlene had figured out how to make her lovers cum without even touching their cocks, and in this position, either on the swing or on his back, she took delight in making her lover ejaculate just from the pleasure of her she cock stretching his ass.
"You're mine," she told him.
"Why would I want to go," he asked, feeling something strange. His cock spurted a little bit, although not a full organism.
The look on his face let her know that she made him have a mini orgasm. She reached out to touch his cock, not squeezing it, but rubbing the tip with his love fluids. She put her wet finger up to her mouth and sucked it. "Oh lover, I want to make you cum more than that."
He bit his lower lip and closed his eyes, but she wouldn't let that happen. "Look at me, love. I want you to look at me when you cum. I want you to see the one who made you cum with her cock in your ass."
Her own pleasure levels were high, but she wasn't going to have to wait long for him to ejaculate. She was angling at just the right point, which is how the swing was made, and soon he was spurting and moaning, trying to look her in the eyes. "That's it, baby," she smiled lovingly at him. "That's it, cum for me."
She began to grab his body and thrust harder into him, "And now, it's my turn," she proclaimed as she continued to thrust.
He was still spurting a little bit when she shot her load into his ass for the second time of the evening. "You're all mine," she moaned. "You're all mine."
"I'm not arguing." There was a hint of vulnerability in his eyes. "I'm all yours."
She helped him down from the swing, and they went to her bedroom. She turned on the TV and they relaxed, cuddling in bed. They spent the weekend together and made love a few more times when she finally said what was on her mind. "Will you move in with me?"
He looked at her in surprise. "Really? But we just met?"
"I feel like I've known you forever, and don't tell me you don't feel it too," she said as she kissed him.
He looked at her for a moment, a little fear in his eyes. Then he realized, what she was asking for was exactly what he needed. "Of course. We'll move in together, Darlene. Nothing would make me happier."
Just like that, they became a couple, and it would last for the rest of their lives. Devon liked Joe as a father figure and Darlene felt confident enough to take the big job and leave Devon in Joe's care. They had plenty of passion in the bedroom, but they also enjoyed going many places together as a family.
Joe never could have imagined his life would be where it was. To the outside world, he might have looked like the man of the house, but in the bedroom, he was very much Darlene's bottom, pussy boy. He wouldn't have it any other way.
