Deceased mother's lover forcefully recreates relationship with daughter
Chelsea Rollington was puzzled by her recently deceased Mother’s finances. Growing up it seemed that her father was often involved with business investments that went bad, and also liked to gamble at the casinos and the racetrack. Although her parents had wealthy parents, the family wealth had long since diminished, and money was often tight in the household. Her parents had also mysteriously sold their house in a prestigious lake community two years earlier. They had dearly loved the home, which they had lived in for decades, but suddenly told her they wanted to downsize to a small apartment nearby. Unfortunately, shortly after they sold the house, her father passed away from a heart attack.
What puzzled her was that even though her parent’s finances were shaky, they always seemed to have the money to send her to prestigious private schools. She had earned a bachelor’s degree, an MBA and now just completed her law degree, all from Ivy League universities, along with experience in prestigious management consulting companies in between her degrees. She asked her mother a few times over the years how they could afford her schooling, when they often had trouble paying their other bills, but her mother was evasive. Chelsea thought that maybe her grandparents had set up a trust for her education, but her mother said they hadn’t.
Chelsea had her own apartment near the university campus. Her mother had cancer and passed shortly before her graduation from law school. As the executor of the estate, she was curious about what assets and debts her mother’s estate had. When the lawyer read the will, she was shocked to find out that her mother had no income except her social security, as she had only kept things going financially the last two years by borrowing money, and also had debt for medical bills. Chelsea had actually co-signed for some of the debt, which she thought was just her helping her mother out with short term cash flow issues. Chelsea was turning 30 years old on Labor Day, and although she was starting a job with a law firm in mid-September after her birthday, she was worried about how she would pay off the portion of her mother’s debts that she was personally liable for, as she had no money of her own.
When she went through her mother’s personal papers, she found a letter from her mother addressed to her. The letter told her that if she ever needed help after her mother passed, she should contact James Peterson. The letter said that he lived in the very large house that was across the lake from Chelsea’s family home. Chelsea had always admired this house, which was modern in design and had several levels built into the side of the hill rising up from the lake. Along with the letter were several pictures of her mother with James, including a picture of her mother reclining on a couch in a beautiful knee length blue nightgown.
It all made sense now. Her mother had told her stories of a mystery man that she went to college with. The man came from a blue-collar family and attended the college on a scholarship. She was madly in love with him and they had a passionate love affair. But her grandparents were against her mother dating James, as they felt he wasn’t good enough for him and wouldn’t be able to financially support her. Instead her mother met her father through mutual family friends. While he had the right pedigree and her mother got along with him well, you could tell there was no passion in their relationship.
Chelsea was a stunningly beautiful woman, 5’-8” tall, with auburn hair and green eyes, and a slender yet athletic figure. She had several boyfriends over the years, but she hadn’t yet met a man that would send her heart racing and would be the only one for her. Men also tended to focus on her looks, not her intelligence, often wanting just a sexual relationship. Chelsea packed up her mother’s belongings and put them in storage, as the rent was way past due on her mother’s apartment. Chelsea’s new job was several states away, so she was staying with a friend for the summer and had just vacated her apartment too.
The next day at her friend’s apartment she decided to call James Peterson. She was very nervous as she called him. “Hi, is this James Peterson?”
“Yes, who is this calling?”
“It’s Chelsea Rollington. You don’t know me, but my mother said I should contact you after she passed if I ever needed any help.”
She wasn’t sure how he would answer. “Chelsea, it is great to hear from you. I thought I might hear from you someday, but I assume there is some bad news about your mom?”
“Yes, she passed last month from cancer and I am the executor of her estate. In her papers I found a letter telling me you live in the beautiful house across the lake from our home. Well it was our home, but mom and dad sold it about two years ago.”
“That is surprising to me. They loved that home. I first met your mother when we were in freshman year of college, when her parents owned the home.”
“James, I think they were having some financial problems over the years.”
“That doesn’t surprise me Chelsea. Your mother and father were far better at spending money than at making money. Why don’t you come up this weekend and we can get to know each other,” he said in a friendly way.
She was concerned about what his intentions were. “I would like to come meet you, but please don’t get the wrong idea. I don’t even know you and not sure what you are expecting of me.”
“Chelsea don’t be silly. I am old enough to be your father and would never disrespect the memory of your mother by making a pass at her daughter. After your mother left me, I was very sad for a while, but eventually met my late wife and we had a great 30 years together, but like your mother, cancer took her from me about a year ago. Your mother and my late wife were the only two women I ever dated, and I haven’t dated anyone for the last year.”
“I am so sorry to hear that and I’m sorry I misunderstood. I would love to meet you. My mom talked about you sometimes and I could tell by the look in her eye when she did that you had something very special together.”
“Don’t get me wrong Chelsea, I loved my wife. But your mom was the love of my life and I regret that her parents kept us apart, and that she went along with them. I spent many years trying to prove them wrong about me and ended up becoming quite comfortable financially, owning several companies. As you know, your father came from a wealthy family, but he lost it all over the years. Your grandparents eventually realized who was the better man, but by then your mom and I both had married so we didn’t want to break up our relationships, as our mates were good people and didn’t deserve that.”
Chelsea drove towards James Peterson’s lake house, through the woods on a Friday afternoon. She was planning to stay in a hotel in town after meeting with him. As she was nearing the house, a sudden heavy thunderstorm rolled through and it became very difficult to see. Lightning hit a nearby tree, and it fell across the road in front of her and she couldn’t stop in time. Her car hit the tree trunk, and everything went black.
When she awoke, she was in the house laying on a couch and looked up to see James looking down at her with a worried face. “Chelsea, are you okay?”
“Yes, I’m okay. How much damage did I do to my car?”
“Well let’s put it this way. You are in much better shape then your car. The roads are blocked, and it will take until Monday for the roads to get cleared enough for me to get you to town to your hotel. I took your suitcase out of the car and put in the guest room. You might want to go take a nap while I make dinner for us.”
“James, thank you so much. You are everything my mom always said you were. A kind gentleman who always thinks of others. This was a strange way for us to first meet, but fate has a strange way about it.
“Well she did bring out the best in me. It is good to finally see you in person. You look exactly like your mother did at your age.”
Chelsea was puzzled by that comment. How did she know anything about her if her mother was not in contact with him for the last 30 years? How would he know what her mother looked like at 29 if they stopped dating when they 19? Although he was nearing 50, he was very good looking, with brown hair with flecks of grey and piercing blue eyes that just looked right through you.
After Chelsea woke up from her nap, she saw that James had made an early dinner for them. Over dinner and all evening, they talked about their lives and about Chelsea’s mom’s dating James during college. Her mother had actually told her that for a brief period she was dating both James and her father, and she wondered if James was actually her father.
“James, can I ask you a question that you might not want to answer?”
“Sure, what is it?”
“Are you my father?”
“No Chelsea. After your mother got pregnant, we both wondered who the father was, but a test showed it wasn’t me. Any father would be happy for you to be their daughter though. You obviously have turned out to be a very accomplished woman and your mother was very proud of you.”
“James, how do you know that? You didn’t have contact with my mother after you two broke up.”
“Well actually we did. Each year on your birthday, she would send me pictures of you and update me about your family, and I would do the same about my life. We never told our mates or you about us being in contact, because they might not understand and get jealous.”
She now looked at this stranger and she was so jealous that her mom got to be his girlfriend and could have been his wife. He was confident without being cocky and smart without being pretentious. Although he was 20 years older than her and very mysterious, she was growing excited with the way he seemed like he was looking at her, although she thought maybe it was just her imagination.
“James, I found these photos of you two with the letter."
He looked at the photos fondly, especially the one with Chelsea’s mother in her blue nightgown. "Yes, I remember these photos well, especially the one of her in the blue nightgown. That was taken the night she gave me her virginity.”
Chelsea blushed a little. “That was a little too much information.”
“Sorry Chelsea if I embarrassed you. Your mother and I were both very shy when we first met but we just clicked and became very comfortable with each other. Our relationship was both intellectually and very physically passionate. We just couldn’t keep our hands off each other. We were a little kinky too after a while,” he smiled slyly as he spoke.
“She would sneak out of her house to see me when my parents were out and would keep some clothes over at my parent’s house. I actually kept them after she left me as a remembrance of her but hid them from my wife. They are in the closet of the guest room. I even have the blue nightgown in this picture.”
“Really, that is crazy. I would love to try on the nightgown if that is okay with you. I am the same size my mother was.” She didn’t know what possessed her to ask to wear very sexy lingerie that her mother wore, in front of this total stranger. But her heart was racing, and she wanted this man to want her like he wanted her mother.
“Chelsea, I would love that, if you feel comfortable. But I can’t guarantee that this old guy will be able to control himself if I get flashbacks of your mom,” he laughed.
“James, you are not that old and look even younger than you are. I might like if you can’t control yourself and you seduce me like one of those cheesy romantic comedy movies my mom said she used to watch.” She winked at him. She couldn’t believe she was flirting with this man, but just couldn’t help herself.
She went into the guest room and opened the closet door and saw the nightgown, along with some dresses, as well as shorts and tops folded on a shelf. James had clearly loved her mother and never gotten over the breakup. Chelsea stripped off all her clothes, except her panties and put on the nightgown and looked in the full-length mirror and smiled. A shiver went through her, as if her late mother’s soul had entered her body and she knew what she wanted from this man she had just met, since it had so quickly felt like she had known him her whole life. She opened the door and walked out in the nightgown and stood in front of him. While she was changing her clothes, he had also changed into red silk pajamas.
James was shocked. She looked so much like her mother. It was if he had gone back in time 30 years. “Chelsea, you look enchanting; just like your mother did. I feel guilty though, like I manipulated you into putting on her nightgown. I hope you don’t mind that I changed into my pajamas.”
“You didn’t manipulate me. I wanted to do it. I had to do it. I want to feel like she felt when you two made love together. I want to do the things you two did.”
“Chelsea, are you sure about this? Like I told you, we were a little kinky. Your mother and I had a bit of a fetish that when we were together, she had to do anything I wanted sexually, wherever and whenever I told her to. She wasn’t allowed to ever say no.”
“James, I want that too.” Her mind was lost now in whatever was going on, which felt like she was channeling her mother from the other side.
“Okay. We had a ritual at night before bed. She would come out of the bedroom in that gown and reach down under it and take off her panties. She would lie across my knee on the couch and tell me the naughty things she did that day.”
Chelsea just nodded her head and reached under the nightgown and pulled down her thong panties and took them off and let them drop to the floor. James walked over to the couch and sat down. He put up his hand and motioned her to come over to him. She obediently laid across his lap.
“Chelsea, tell me what you did naughty today so you can get your punishment.” He started rubbing her buttocks on the material of the gown in a circular motion.
“I went over to a strangers house and decided I wanted him to have me, even though he dated my mother. Only a naughty girl would do that.”
“Okay then you need to be punished.” He started spanking her over the material of the gown, moving his hand to each spot of her butt cheeks. But then he surprised her and suddenly pulled up the hem of the gown, exposing her bare ass.
She became embarrassed and was shocked and pulled the hem back down. “Hey, I was just kidding around. I didn’t say you could do that.”
“I guess you are just like your mother with the fake shyness. Remember you made a deal to be just like her. You can’t say no after we start our little game.”
He pulled the material up again, exposing her ass to him, but she didn’t resist this time. He started spanking her again, but the spanks got harder and harder and her ass got red. Tears started welling up in her eyes, but her pussy also starting to get sopping wet and she started grinding against his crotch and could feel his hard erection through his pajamas. She could tell he was not wearing underwear. She wanted so bad for him to make her cum but was too embarrassed to ask.
He sensed her excitement and dipped his finger down and inserted it into her sopping wet sex. “Chelsea, you are very naughty. It looks like you want to get this old man to scratch that itch you must have.” He started rubbing her clit in circular motions while he still slowly spanked her. She could feel her orgasm growing. He stopped spanking her though while he kept fingering her and wet a finger on the other hand. He reached to her rosebud and as soon as she felt his finger touch it, she got very scared.
“James, no one touches me there. I’ve never even put my finger in there.”
“Well you are going to feel this finger inside it now. Remember the word ‘no’ does not exist anymore. He slowly inserted it and she didn’t feel any pain. Just a weird sensation. He moved it around inside her in a circular motion, like he was doing on her clit with her other hand. She couldn’t take it anymore and started shuddering as the orgasm overtook her body. James felt her asshole contract in pulses as she came.
After she recovered, she turned over on his lap and looked up at him shyly. “What would you guys do next after mom’s spanking.”
“She would get down on her knees and pull my pants down and suck my penis.” Chelsea wordlessly got off his lap and got on her knees and pulled his pants down to his ankles, as his stiff large cock sprang to attention. It was above average size, but very wide. She just looked at it for a moment and dove down on it with her open mouth, like a robot at his command. She didn’t even bother to tease him. She just put it down her throat as far as she could until she started choking on it and bobbed back and forth on it. This older man could certainly still get it up like he was a teenager again, but she didn’t want him to cum in her mouth. She wanted it inside her.
“James, what would the two of you do next?”
“She would straddle me and ride me like a cowgirl,” he laughed again. Like she was in a trance she straddled him and didn’t even wait for him to insert himself into her. She put his thick cock inside her vagina and started rocking back and forth on him. After a while she could feel him breathing harder and she was afraid he would cum inside her and she wasn’t using birth control that day.
“James, you need to pull out, I am not on anything and I don’t want to get pregnant.”
“It’s okay Chelsea, I’m not able to have children. I can cum in you.”
Chelsea was relieved and started rocking back and forth on him again. She felt another orgasm rising and felt him starting to lose control too. They both came at the same time with thundering orgasms and she could feel his sticky fluid flood into her pussy.
After a while he became soft but kept his cock in her and held her tight as they kissed each other lovingly, as his fluids leaked out of her. “Wow, James, that was quite a load you put in me,” she grinned.
“I haven’t had sex since my wife passed and that was unbelievable. It felt like it did with your mom all those years ago.” Chelsea smiled and felt like her mother was looking down on them approvingly.
“Let’s go to bed Chelsea. You wore this old man out. I am glad I didn’t cum in your mouth. I would have never been able to go a second round and get the honor of being inside you.” She smiled at him and walked with him hand and hand into his bedroom. That was the nicest thing any man had ever said to her. She didn’t even put her panties on again, as she was hoping he would take her again.
They spooned together in bed as she fell into a deep sleep. But as dawn broke, she felt a strange feeling between her legs, like she was dreaming of having sex with James the night before. She opened her eyes and saw James between her legs greedily lapping at her pussy and clit. She smiled at him and said, “was this a tradition between you two also?”
“Yes, whoever woke up first would wake the other person up with their tongue before we had sex again.”
“That sounds like a great wake up call.” He got up on his hand and knees and turned around and straddled her so she could suck his cock while he pleasured her with his tongue. She sucked on it and eventually stopped and started licking his balls while she jerked on his hard member.
“Chelsea it is time for the main course.” He rolled her over on her back and told her to pull her knees up to her chest, which she did. He reached into the draw and pulled out a small butt plug and a bottle of lube.
She got scared again. “Hey James, I let you put your finger in my butt, but that is too big for me.”
“Relax Chelsea. Your mom liked to feel very full when I was inside her and I want you to feel that way too. Remember you promised not to say no.”
He smeared the lube around the inside of her tight hole and opened her up with his fingers, then slowly inserted the butt plug. She winced a little but then got used to the size of it. She put her legs down and he entered her in one swift motion. Her mom was right, it felt very strange, but felt wonderful after a while. He pulled her nightgown up above her breasts, which he had never seen before, and started sucking on them as he rocked in and out of her slowly, as she softly moaned with pleasure. She wrapped her legs around his waist and grabbed his ass cheeks to pull him into her deeper and deeper. She wanted to feel his cum in her again and he did not disappoint, as he soon groaned and released hard into her, as she came with him again.
“Wow, James, you and mom sure had some tricks up your sleeve. And in her ass too,” as she gazed at him dreamily and they kissed again.
They eventually got up and took a long shower together, rinsing off all the sweat and cum from their trysts. This wasn’t like one of those porn stories though, where the guy can come 5 times consecutively. James always needed time to recover before he could get hard again, even when he was younger. They had breakfast and then Chelsea said, “what are our plans today?”
“Well, it is going to be very warm, so let’s go for a swim in the lake. I have a little beach and private dock with my boat there.”
“That is a great idea. But I didn’t bring a bathing suit with me.”
He smiled at her.
“Let me guess, you still have a bikini from mom,” as she grinned at him. She went into the closet and sure enough found a string bikini that was in one of the pictures. It was a beautiful flowered pattern. A little faded and out of date, but she didn’t care. She put it in on and came out the bedroom, and James nearly fainted. Chelsea again looked like her mom from 30 years ago. They went down to the dock and got into his boat. They took it for a spin around the lake and came back in an hour and docked it. They walked to the beach from the dock and went into the water for a swim, then laid out towels so they could sunbathe and dry off.
After a while, James reminisced in his mind about the times he spent on the beach with Chelsea’s mom and he started developing a tent in his bathing suit. He rolled over to face Chelsea, who had her eyes closed as she sunbathed and whispered in her ear. “This reminds me of days when we would find a deserted beach and make love.”
He suddenly pulled her bikini bottoms down to her ankles and pulled up her bikini top over her breasts. “James, no. Someone will see us. We can’t have sex in public. You’ve gone too far. I won’t do this.”
He rolled her over on her stomach and held her down and took off her bikini. “I am not asking you I am telling you. Your mom did it in public many times when I made her do it.” She just wanted him to finish quickly and hopefully the neighbors wouldn’t see. “Get up on your hands and knees.”
Chelsea grudgingly did what she was told. He pulled off his trunks and started massaging her breasts which were hanging down and she started getting aroused. “I don’t care if anyone sees us. I want everyone to see that we belong together.”
Chelsea was worried that James was flashing back that he was with her mother, not her, and felt a little jealous. She was getting wet though thinking about how her mother had felt when he took her in a public place. She didn’t have long to think about it though, as she felt his hard cock suddenly spear into her pussy. As he slapped against her butt over and over as he took her from behind, she didn’t care anymore about the neighbors.
He stopped and pulled out and she was puzzled. He moved around in front of her and told her to open her moth, which she did. She wanted to claim that magnificent dick for hers to own. “Chelsea you had one more orgasm than me. You owe me one.”
She opened her mouth, but said, “don’t cum in my mouth. I don’t do that with guys.”
“Chelsea, I thought we had an understanding. Your mom would suck my cock and I would cum in her mouth at the end. She would open her mouth to show me my cum and then she would swallow it and show me her mouth again to prove she swallowed it.”
Chelsea was broken now and would do anything to please James, like her mom always did. She sucked his cock eagerly now, feeling competition with the memory of her mom. He soon came hard in her mouth and she swallowed every drop and licked her lips to show him she liked it. He patted her on the head and said, “your mom would be proud.”
She was starting to get mad though that maybe James was just using her to relive his memories of 30 years ago. But she felt compelled to just do what he wanted. They went back to the house and he told her they were going to go out to dinner at a fancy restaurant. Of course, he had one of her mom’s fancy dresses in the closet, which was actually a classic that was still in style. They went out to the most wonderful restaurant overlooking the lake, which she had never been to before.
They spent hours eating, drinking and talking about their lives. She told him about her disappointments in relationships, and he talked about his late wife, but in the conversations lamented about not having children, because his sperm count was too low. They thought of adopting but he was so busy with his businesses, and his late wife had a busy job as a top lawyer, so they never got around to it.
When they got home, she went to go take the dress off, but he motioned her to come over to the couch so they could watch a movie together. “James, this odd. You and my mom used to go to dinner then watch a movie in your dinner clothes?”
“Yes, it was another ritual we had. We would watch a cheesy romantic comedy movie and make fun of the dialogue and plot.” He found a silly romcom on cable and put his arm around her shoulder, and she felt so safe in his arms as they watched it. A half an hour into the movie he slowly took down the straps of her dress over her shoulders and started feeling her breasts and licking her nipples as she watched the screen.
“Chelsea, we would start watching the movie but then make our own x rated version of the movie the way we wanted it to be. He then rolled her over on her side against the arm of the couch, which puzzled her. He pulled up the dress exposing her ass cheeks, since she wasn’t wearing panties. He pulled out a bottle of lube he had hid in his pocket and started putting his lube covered fingers inside her ass.
She knew where this was going. “James, I told you I don’t take cock up the ass. I took the small butt plug, but your dick is much thicker, and it will hurt. I don’t care what my mom did with you. What are you going to ass rape me if I say no?”
“No, I am just going to take what you never gave to anyone else. Now please give yourself to me completely like a good girl.”
She knew she couldn’t resist him anymore and after he took down his dress pants to his knees, she got on his lap, and he entered her ass slowly. He had opened her up a lot, so it didn’t hurt at all. Obviously, James had an anal fixation, since he seemed to love spanking, using a butt plug with vaginal sex, and having anal sex. She bounced up and down on him while they watched the cheesy movie, where the guy barely gets a kiss at the end of the movie.
“Chelsea, play with yourself while you give me your anal virginity.”
“James, I’ve never done that in front of a man. It’s embarrassing.” She caught herself though before he could respond, telling her she had to do it. She started playing with her clit furiously as he came deep into her bowels while he massaged her breasts. She came right after him with the strongest orgasm yet. She wasn’t competing with her mom anymore. If she had just met James through friends, she would be doing the same things as her mom did if he just asked her to. She now liked anal sex and hoped she had pleased him as much as she knew he wanted to please her.
After they finished, they held each other for a long time and finally got up to go to bed. As they walked to the bedroom he laughed and said, “the dry cleaner is going to wonder about these stains on our clothes.”
When she woke up, she didn’t see James next to her and got scared. She found and bathrobe and looked around until she found him on the deck overlooking the lake, with a full breakfast on the large dining room table. He was wearing his red silk pajamas, which she loved the look of. She was ready for a great breakfast and a day at the lake again, when he said, “Chelsea, before we eat breakfast on the deck, we need to have an appetizer. He started taking off his pajamas and he said, “take off the robe and lay on the table.”
She knew she couldn’t say no anymore and did what he asked. She didn’t care about the neighbors anymore. She didn’t care about her mom anymore. She just wanted him whenever and wherever he wanted her. She took off the robe and sat on the table, next to her breakfast, which was now getting cold, but she didn’t care. He got on top of her and they didn’t have sex; they made love, in many different positions. They knew they had found something special and didn’t want to let it go.
Chelsea moved in the next week, and she knew they only had three months until the end of the summer, when her 30th birthday would come on Labor Day, and then she would have to leave for her new job 500 miles away. She didn’t want to have a long-distance relationship, but also wanted a career.
They had a happy, passionate and bit of a kinky relationship, but one day Chelsea started getting upset, which surprised him. She started sobbing and finally cried out, “I feel like I am competing with my mother. She’s gone and I only have memories of her, but your memories of your time with her is all you have. You don’t care about me. I am just a clone of her!”
“Chelsea, that is not true. Maybe it was that way in the very beginning, but knowing you now, you are your own person, not a clone of your mother. You may look like her, but you are unique and special to me in your own way. When we are together, I am with you, not your mom.”
She felt better and they enjoyed the summer together. James had executives managing his various companies, so he only had to work part time and told Chelsea about what each company was currently working on.
When Chelsea’ 30th birthday came on Labor Day, they were both sad that they would soon have to part and weren’t sure what would happen to their relationship. James took her out to a dinner again at the restaurant they had enjoyed earlier in the summer, and when they returned they watched a cheesy romcom and made their own x rated version while they watched it, and laughed while they were doing it.
Afterwards James told her he had something to tell her and Chelsea dreaded that he might tell her that he was breaking up with her.
“Chelsea, I have something to tell you that you should know, although you might think bad of me after I tell you.”
“What is it?” she asked worriedly.
“I was the one who paid your private school tuition all these years.”
Chelsea was shocked. “why would you do that? I’m not your daughter.”
“I couldn’t have a child with your mother and wanted to be married to her and have one but couldn’t do either. When I saw pictures of you and heard about your life, I was worried that they would never have enough money for you to get a good education, because they would waste all their money, which they ended up doing. I held the tuition funds in trust and paid the bills myself directly.”
“Why didn’t anyone tell me this when I was growing up?”
“Because your mother and I didn’t want my wife to know, because she might wonder if I was cheating on her with your mother, which was not the case.”
“James, why didn’t tell me when you first met me?
“Because I didn’t want you to feel obligated to me because of money and wanted you to love me for I am, not for what I did for you.”
“I understand. But I would have fallen in love with you either way, but now you know my love is true and not about what I didn’t even know you did for me. I want to make my own way on the world, and since I am leaving you don’t have to be concerned that I am just after your money.”
“Chelsea, I would never ever think that. I have something else to tell you.”
“I am really afraid to hear this. I am still trying to process what you just told me.”
“I was afraid that your parents would go broke even after I paid for your tuition, so I set up a trust for you that you would be able to draw on once you turned 30 years old.”
Chelsea was speechless. “Why would you do that?”
“When I saw through the pictures and emails from your mom what you had accomplished, I knew you might need help after you mom passed. I knew she was sick, but she never told me she was terminally ill. I knew she had probably built up debts you might need to pay. I was going to have her tell you when you turned 30 but she passed before that.
He took out a bank statement and showed her the amount of money in the trust and was astonished. It was enough that she would never have to work, but she didn’t want that.
“James, this is generous of you, but I can’t accept this.”
“Chelsea, my company’s general counsel could use some help managing some of my businesses, and she could give you great training to be a lawyer. I wouldn’t be giving you anything, the yearly payments would just be equivalent to a market rate salary for a lawyer who also has an MBA and some experience. You could stay here with me.”
“James, I would love that more than anything.”
“But there is one thing. We won’t be able to have children of our own but could adopt one.”
“Well I have something I was going to tell you too.”
“Chelsea, what is it?"
“I’m pregnant. Your sperm count may be low but maybe I willed them to swim better because they really wanted to get to my egg. You’re not the only one who won’t take no for an answer. I want to have a family with you and spend our lives together.
“But Chelsea, don’t you think I am too old for you?”
“I don’t feel that way and your sperm don’t think so either. You have more sexual energy with me than guys my own age. But from now on sometimes I want to give the orders in bed, and you can’t say no.”
“You are a tough negotiator, but I agree Chelsea. I promise.”
Chelsea’s mom’s spirit saw this scene from the other side and smiled that they had both gotten the second chance at love they both deserved. Her spirit laughed to herself that Chelsea and James had together created the most farfetched romcom a writer could ever dream up, patching together every cliché imaginable, except every scene was true. In a good romcom, there is always conflict between the two, but the guy always gets the girl in the end. Sometimes in the rear end.
They looked at each other and he hoped they would have a great evening of wild sex. She slowly turned to him and said, “now wait here James, I have a special treat for you, but you have to close your eyes while I put my mom’s nightgown on. Go put on your pajamas too. Mom told me about everything you guys did, and there is one thing you never did with her. You have to promise though you will do whatever I want.”
“I promise Chelsea.”
He waited patiently but nervously with his eyes closed. He tried to remember what Chelsea’s mom had done with him and what they hadn’t done. He thought they had done everything a man and woman can do with other. Maybe Chelsea was going to suggest a threesome? He never did that with Chelsea’s mom.
Chelsea came out of the bedroom and walked over to the couch and sat down. She said, “now open your eyes and come over to me.”
He opened his eyes and saw her in the nightgown and walked over to her excitedly.
“Now pull down your pajama bottoms and get over my knee.”
He didn’t question her and just smiled and obediently got over her knee and thought he knew what was coming next. As she softly spanked his bottom, he reached for her pussy, expecting something warm and wet. He felt something weird though. He looked over to her as she opened her legs and pulled up her nightgown revealing what she had tucked down between her legs. He was horrified to see a strap on dildo between her legs.
“Chelsea no. I won’t do that. I am not into that. With me it is an exit only, not an entrance.”
“James, turnabout is fair play they say. And you can’t say no, remember?” She pulled out a bottle of lube she had hidden under the couch seat cushion and squirted some onto his now quivering asshole, and slowly stuck a finger in.
“Chelsea, please no.”
“Yes James. Now tell me all the naughty things you did to me these past months. By the way, have you ever heard of a woman milking a man’s prostrate?”
“Yes, Chelsea.”
“I like that word yes. I am going to enjoy hearing that word a lot more from you.”
“I love you so much Chelsea. You can do anything to me you want to.”
James winced as Chelsea pulled her finger out of his ass. “Now get down on all fours James, like a good doggy. Time to take your punishment.” She got down behind him and he knew what was going to come next. It was going to be a long night. Chelsea was right. She was not her mother. She was much kinkier than her mother and had big plans for James sexually going forward. He might not like some of her ideas at first, but she knew they would never say no to each other.
Chelsea’s mother’s spirit looked down on the scene with amusement. Chelsea had created her own version of a romantic comedy. This one is where instead of the guy getting the girl in the end of the movie, the girl gets the guy in the end. Sometimes in the rear end.
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