Samantha was looking for a quiet room with reasonable rent. Richard was looking for a girl to perform the wifely duties that his late wife used to.
Richard Stevens was lonely. He was 62 and his wife had passed away the year before. He lived alone in his large suburban home on the East Coast. They never had children, just dogs and cats who had also passed on, so the house was a little too quiet. He had many friends, but most were couples and he felt like a third wheel. After a long happy marriage, he didn’t want to get married again, as it would never compare to what he had with his wonderful late wife. He didn’t want to even have a serious relationship, but he had needs. A need for some companionship and a need for sex, as he still had a high sex drive and ED medication that helped make those urges a reality. He dated some woman within a range of respectable ages, but also used the services of escorts in their 20’s, whom he had nothing in common with. He just wanted to savor their tight young bodies.
He lived within walking distance of a major university and thought of an idea that might provide the best of all worlds for him. He could rent out one of his bedrooms to a female college student at a discounted rate, in return for household duties like cooking, cleaning and laundry. He would have some companionship and not have to deal with outside companies for these services, while also paying for part of his monthly expenses.
He had no intention of getting romantically involved with someone young enough to be his granddaughter, but maybe he could manipulate her into a Sugar Daddy arrangement in exchange for free rent and food, instead of just a discounted rental rate in exchange for household chores arrangement.
He put an on-line ad on the universities’ jobs web site for students looking for housing and received a few calls, but they were suspicious of his intentions. Then he got a call from a student named Samantha, who had a real interest and was comfortable with his proposed job duties. She came over to meet with him.
“Hi Samantha, it’s great to meet you” Richard said cheerily as he opened the door. Before him stood a beautiful but wholesome looking girl, about 5’-9,” with medium length brown hair, but her outfit showed that she was in great shape and looked like she was into sports. She had average size breasts, but they were very solid looking.
“It’s great to meet you too Mr. Stevens,” Samantha replied in a giggly voice.
“Come on in and I’ll give you a quick tour of the place.”
They walked through the house and Samantha marveled at how spacious, well decorated and clean the house was. You could literally eat off the floors and it was not cluttered like you might expect from a bachelor. Everything had its place.
“Wow, your home is beautiful and so clean. Why would you even need someone to clean it?” Samantha asked with a puzzled look on her face.
“I am semi-retired, but work part time as a financial consultant and do some travel for my work, as well as travel for pleasure. “I also have some back issues, so I need to be careful about cleaning, carrying groceries and other things that could strain it.” This was a total lie; he spent many hours in the gym and was in great shape. “I am very particular about my home, so I like it very clean and am not a very good cook either. My late wife spoiled me with her gourmet cooking.”
He showed her the bedroom he had picked out for her, right next to his bedroom, and her eyes nearly popped out of her head.
“This would be my bedroom? It is so huge, and the bathroom is too, and the walk-in closet is enormous.”
“Well Samantha, we did spoil our sons a little. It doesn’t cost much to make bedrooms a little bigger when you build a house and they lived home during college and actually attended your university.”
“Please call me Sam. Everyone does.”
I am a little old fashioned so I would prefer if you call me Mr. Stevens.”
“Okay, I understand.” My Mom and Dad always wanted me to call them Mom and Dad, while some of my friends call their parents by their first name, which I think is a little too informal.
“Sam, let’s sit in the kitchen and you can tell me a little about yourself.” Richard could tell Sam was very trusting. This felt like the old poem ‘The Spider and The Fly.’
“I don’t where to start Mr. Stevens. I come from Nebraska, but the university down the street here has a nationally ranked soccer team. I started school near home, but got a partial soccer scholarship here, but it doesn’t include room and board. I am an only child and had a nice bedroom and bathroom in our house, so the idea of living in a small dorm with other girls is not that appealing to me. I also have a lot of practice time but also need time to study for my degree in finance, so I don’t want to be interrupted by partying classmates making noise late at night.
“Since I have a degree in finance, I could help with your homework any time you want.”
“That would be great. The rents are extremely high, being so close to the city. What would the monthly rent and food rate be and what would my household duties be?” Sam said shyly.
When Richard told her the rent and food cost, she looked at him in disbelief. “That is a great rent for that room, especially with the privacy.”
“Sam, I am not looking to be a landlord here. I could use a little help with the household work here and it is a little too quiet here with my sons moved out the house.”
“I understand Mr. Stevens. My mom passed away a few years ago and my Dad is a little lonely too.”
“Are you good at cleaning, cooking and laundry?” he slyly asked.
“Yes, I love to take care of a home. After my Mom passed I kind of became a substitute wife for my Dad. He has dated a few women, but never has gotten serious enough for any of them to move in and take care of him.”
“Sam, would you be comfortable living alone with a single man?”
Samantha blushed at Richard. “Of course, you are much older than my father. You are actually old enough to be my grandfather. I didn’t feel like you were a dirty old man when I saw your ad. Just someone who needed household help and some company, while I need to keep my expenses low, so my father and I don’t have to borrow too much money for school. I feel it could be a mutually beneficial relationship.”
Richard felt like this was a real possibility to get what he wanted. A Sugar Baby who is not a manipulative bitch. He had enough manipulative intent in him for the both of them. “Sam, where are you living now? School is starting soon.”
“I had to arrive in town early to start practices, so I am staying with a family friend temporarily, since she has an off-campus apartment and is waiting for a new roommate to move in.”
“Well I look forward to you moving in, I think this will be great for both of us.”
“I feel the same way.”
Samantha moved in a couple of days later and they settled into a routine. She had classes and practices most days, but she found plenty of time to do the cleaning and the laundry, since there wasn’t much to do of either. She either prepared meals in advance for Richard or made them that day. Some days they ate together and some days they ate at different times. Richard helped her with homework for her finance classes and she appreciated that.
One day she came home from soccer practice limping and in pain and Richard was concerned.
“Sam, what happened, you look like you had a rough practice.”
“Yeah, I went sliding for the ball and hurt my calf and my back and shoulders.”
“I’ll help you up to your room so you can rest.” When they got up to her room, she laid on her bed but was still in pain.
“Mr. Stevens, my shoulders, back and calf are all cramped up. Do you think you could massage some lotion onto them?"
“No problem, Sam. Just take off your socks and roll over and I’ll get the lotion.” When he came back, he saw that she had not only taken off her socks, but also her jersey, but she had a sports bra underneath it, so she did not think anything of it. He couldn’t believe how muscular her legs and shoulders were from soccer and he hoped one day he would not only see her naked, but actually have her in his bed.
He started slowly rubbing the lotion onto her shoulders, back and the back of her legs, and thought he would cum any minute, as he started getting rock hard.
“Oh, that feels so good,” Sam cooed. “Thank you so much.” As he massaged her more and more, Samantha started feeling aroused and she got wet, which made her feel ashamed. She said to herself “I can’t believe this nice man who is old enough to be my grandfather is innocently massaging me and I am getting excited like a little slut. Well, I haven’t had sex in a long time and hopefully he won’t notice.”
The next day when Sam came home from school, Richard asked her about possibly adding something to her household duties. “Sam, I get cramps a lot in my legs and back too, but not from soccer, just from old age,” he grinned. This was a total lie. “My late wife used to give me massages once a week.” Another lie. Would you be interested in giving me a massage once a week like she used to? I don’t expect you to do it for free, I would reduce the rent a little in return.”
“Mr. Stevens, I wouldn’t charge you for that. You were nice enough to give me a massage when I hurt myself.”
“Sam, it wouldn’t be proper to have a young woman massage me if I wasn’t compensating you for your services. Besides, you are not charging me, I am just lowering what you are paying me every month.”
“Oh, I understand. Thank you for your generous offer; it would be my pleasure.”
After dinner on Friday, they went into his bedroom and he had a massage table already set up. He went into the bathroom and took off his clothes and came out in only a towel wrapped around his waist. He was in very good shape for his age, since he did a lot of running and weightlifting.
Sam was a little shocked. “Mr. Stevens, I didn’t think this would be a nude massage. Are you expecting me to take off my clothes too?”
“Sam, it is hard to give someone a massage with their clothes on. No, of course you are keeping your clothes on, I am not massaging you,” he laughed. He laid on the table and she rubbed lotion over his back and legs. He moaned softly with appreciation so she would know she was doing a good job. He kept the towel around his waist so he wouldn’t frighten her, but he could feel his erection growing.
After a while he said, “that is great for my back, let me flip over and you can do the front.” When he flipped over, he purposely let the towel slip so she could see a little of his cock standing at attention. She tried to ignore it and rub his chest and arms and he put the towel over it a little so he could fake embarrassment. “Sorry about that Sam. Your massaging me reminds me of when my wife used to massage me.”
“You really miss her, don’t you?”
“Yeah, I really do.” This was no lie, but he needed a lie to get what he wanted next. “Sam, at the end of the massage, my wife used to masturbate me to keep the ‘old pipes cleaned out.’ Can you do that for me?”
“I don’t know about that Mr. Stevens. You are like a grandfather to me. I don’t know if that would be right to do something so intimate.”
“Sam, this is just a service you are performing in return for reduced rent, so it is okay.”
She didn’t know that Richard had taken ED medication two hours before the massage, so his cock was now as straight as a flagpole, which made his above average size penis impressive looking. She hadn’t seen a hard cock in a while.
“Ok, I guess it is ok to make it part of the service,” she giggled. She wrapped her hand around his cock and slowly stroked it up and down, occasionally fondling his balls. He was impressed that her hands were also very strong from soccer, and he looked forward to more massages. As she stroked faster and faster, he started to breathe heavier and heavier. He hadn’t cum since jerking off thinking about Sam a couple of days ago. He closed his eyes and tried to hold back but couldn’t anymore and came all over his stomach. Sam was a little red faced, but enjoyed making him cum.
“Sam, that was great. At my age you don’t know how many orgasms you have left.”
“Mr. Stevens, please don’t talk that way. You are still a young man and hopefully will have many more orgasms in you.” She laughed and winked at him. “Will you charge me if I need a massage after soccer practice?” she playfully asked.
“No, giving you a massage would be my pleasure and always free.”
Richard knew that he had reeled her in a bit and needed to change tactics to get what he wanted, since he didn’t know how far he could push her voluntarily.
The next Friday she was changing into her pajamas to get ready to give him his weekly massage and he walked into her room suddenly while she was completely naked. “Mr. Stevens, I am getting dressed! What are you doing in here?” She tried to cover her nakedness.
“Sam, you have been teasing me since you came into my house and I am tired of it.” Another lie. “I don’t think our deal is fair. I gave you a great rent and even lowered it just to get a weekly massage from you with your clothes on. The new deal is that I will lower your rent even more but you have to massage me while you are nude and you need to let me suck your tits and masturbate you too after you finish with me. Otherwise, I think you will need to find another place to live.”
Samantha was shocked at what he just said and a little upset. But she was worried about where she would live if he kicked her out. “Mr. Stevens, you are wrong. I have never teased you. I feel like you are blackmailing me, but I know you are lonely and may have become attracted to me, so I forgive you for being so mean.” Samantha had just found out that her father’s company was not doing well, and all the executives had to take a pay cut, so she was happy with the lower expenses, but still upset that Richard was forcing him to make her massage and masturbate him with them both nude and now had to also let this old man play with her young pussy and suck on her tits. She thought to herself that she could maybe just fantasize that he was a college boy.
Richard thought, boy, these Midwestern girls are so nice. When they tell you off, you can’t even tell that they told you off. “Sam, this is strictly business. You should know that from your business classes. As you’ve said many times, I am old enough to be your grandfather.” Richard felt a little bad that he was manipulating her but he had been very nice to her before this blackmail threat.
She followed him into his room and instead of the massage table, he took off his clothes and they both got on his bed naked. She gave him a great massage like she did the week before and started getting soaked knowing she was going to get a good one too. She was so busy with school and practice that she hadn’t even had time to get herself off. After he shot his load off like a rocket, she resigned herself to the old man fondling her. She weakly smiled at him and said, “my turn.”
She laid on her stomach and he started massaging her back. He pulled her ass cheeks apart subtlety as he massaged them, so he could see her asshole, which he hoped so see more of in the future. She started enjoying the massage, moaning softly, and involuntarily parted her legs a little. He drew his face near her neck and dipped his finger into her dripping cunt and whispered, “I guess I am not forcing you that much?”
Samantha rolled over and smiled at him. Richard started sucking on her tits, alternating between each one. He reached down and rubbed the palm of his hand against her pussy, driving her crazy. She tried to grab his fingers to put them between her pussy lips, but he kept teasing her, pulling his hand away. Finally, he started rubbing her clit while he pulled on one nipple with his fingers while pulling on the other one gently with his teeth, and she shook with a thundering orgasm.
They laid in bed for a while and she looked at him and said “I am very busy with school, practice and my household chores. The deal is you are getting one of these deluxe massages only once a week.”
“That is a fair deal Sam. You are getting to be a very good negotiator.”
“But there is one other part of the deal. Sometimes the stress of my schedule makes me horny and I have to rub one out myself since I don’t have time for a boyfriend. So, if I want a massage more than once a week, you have to give me one, even if I don’t give you one."
“That sounds like a fair deal Sam. It sounds like you are asking for both ‘right of first offer’ and ‘right of first refusal.’ Your business professor would be proud of you."
Richard counted the days until the next Friday massage with Samantha. But on Tuesday he heard her come home late from school. She walked into his bedroom where he was watching TV on the bed. She looked very stressed out.
“Sam, what is the matter?”
She looked at Richard sadly and said, “I had a really bad day today and don’t know how I will go to sleep. I need some stress relief. She took off her pajama bottoms and walked towards him and said, “I am taking right of first offer.”
He pulled her onto the bed and pulled up her pajama top and started massaging her body. He replied, “well you are never going to have me invoke right of first refusal. There is nothing like a good orgasm to help you go to sleep and time to give you a great one.”
“My thoughts exactly Mr. Stevens.” He stroked her gently until she came hard. She looked at him mischievously and started stroking his hard cock, and said, “time for you to get your happy ending before bedtime.”
The following week she told Richard that she was going on a date with a boy named David. He was not jealous of it at all. He was very happy that she was having fun and meeting people at school. He wasn’t trying to own her or control her. David sounded like a great guy, from how she described him. Richard had also started dating a nice woman in her 50’s named Sue, and they were having some great sex. Sue didn’t think anything strange of Richard having a college co-ed living with him doing household work in return for reduced rent. She didn’t know about his negotiations to get more from her in services in return for lower rent.
A few weeks went by, with Richard getting his once a week massage, but Samantha was not asking for any additional ones in between, and that was fine with Richard. They were both very busy and he enjoyed her company.
But at the next Friday night massage session, Richard looked at Samantha stroking his dick and he knew it was time to take the next step. He was also a little jealous that he was only getting a hand job and David was probably getting blowjobs and sex from her. As she was stroking him, he reached out and grabbed the back of her head and pulled it down for her to suck his cock. She tried to pull her head up, but he held her head over his cock and said, “Sam, you need to do more for me than just a hand job. You need to suck my cock. I bet David is getting his cock sucked.”
She started softly crying and said, “I am not having sex with David and I am not sucking his cock. I’ve never done that for any boy. I think it is gross.”
Richard got very excited. He knew she wasn’t a virgin and he was getting a little bored with just the massages and hand jobs, but it was going to be hard for him to the first for her to give head to. He also felt bad for David that she would deny this to David, and maybe deny it any boyfriend or husband in the future. He needed to get mean with her for effect, but he was also frustrated and felt that maybe the rent was too low for what he was getting.
He slapped her cheek, which shocked her. “Sam, I know you are not a virgin, so you not giving head is ridiculous. Now open your mouth, girls have to give head. You will never get married if you don’t do that.”
She still wouldn’t open her mouth and kept trying to pull away. He slapped her cheek harder and said, “Sam, I have been very nice to you, but this arrangement is boring me and maybe I have to get another girl to live here and do more for me. But if you do it as part of our massage sessions, I will lower your rent even more.” This time he wasn’t kidding. Something had snapped inside him and he wanted more from Samantha, no matter how he had to get it.
Samantha thought about it and knew she had a good deal that was now going to get better, so she tentatively opened her mouth and lowered it onto Richard’s erect penis and started bobbing up and down. He had just taken a shower and shaved his body hair so she wouldn’t see any grey hairs on his slightly wrinkled balls, so he didn’t look so old to her. The sight of this beautiful athletic co-ed engulfing her mouth with his penis was like heaven. This was not his normal gentle feelings for her. Tonight, he wanted to totally dominate her.
“Sam, you are doing a great job and your rent is going even lower if you swallow my scum. Not that you have a choice.”
Samantha got used to the feel of Richard’s cock in his mouth and it wasn’t so bad anymore, but she was afraid that when he shot his load it would gag her. He held her head tighter and made her go deeper and deeper but stopped short of her gagging. He didn’t want to be that mean to this sweet girl, but she needed to know who was in charge tonight.
As he was getting closer, he knew she might be scared of him coming in her mouth and gagging to swallow his salty scum. “Sam, so you don’t gag on my cum, my wife had a technique where right before I came she would put her tongue over the hole to deflect it from going down her throat to avoid choking on it.”
She did this just as he erupted, and she had a relieved look on her face. “Now open your mouth and let me see the load before you swallow it.” She opened her mouth to show him the load in his mouth but motioned that she wanted to go the bathroom to spit it out. “No way, Sam. Girls need to swallow it, not spit it out. Now swallow it and open your mouth again to show me.” The young escorts he sometimes frequented were often nymphomaniacs, who loved the taste of cum and would proudly show him his load in their mouth before swallowing. She swallowed it and looked up at him with a look of relief because it did not taste that bad to her.
“Sam, sorry I had to be a little rough with you, but you have been getting a little spoiled with me and you need to respect your elders a little more. Now that wasn’t so bad, was it? By the way, with the deal you are getting now, we are going to just skip the pretense of a massage and you are just going to suck my cock at least twice a week and you don’t get to choose when. I try to be nice, but in bed I can sometimes be a taker. I’ve wanted to have you since you walked in the door three months ago. Men are always plotting how to get a girl. Even when you reach my age. Seduce them, sometimes pay them, or sometimes you just need to force them a little.”
“Mr. Stevens, you had planned this since you placed the ad for a girl to do household chores in return for reduced rent?” she asked with disappointment in her voice.
“Sam, when you interviewed with me, I specifically said your household chores would include the usual ‘wifely duties.’ I just didn’t tell you what all the duties would be. In business, you have to listen carefully when negotiating. Verbal contracts are not enforceable, but we don’t have a contract. I can kick you out at any time I want, and you can leave any time you want. I know I have been a total liar to you at times but have been very generous with my deals.”
“Mr. Stevens, you pay girls for sex? I can’t be bought, and you are not going to be fucking me. I usually only have sex with boys my own age, not old men like you, and they don’t pay me” she sneered at him.
“Sam, I don’t pay girls for sex. It says in their ads that they are being paid only for their time and companionship. The sex is just something that happens between consenting adults. Otherwise it would be prostitution,” he smirked. You are a great companion and take good care of me and my house. I expect you to have sex with boys your own age and I mostly want to have sex with women closer to my old age, but sometimes like to experience a young escort. Many of them just need more money to live on then they can make in their normal jobs.”
“So, what is your relationship with me? Do you think you are my Sugar Daddy?”
“Sam, that was originally my plan, but I am not sure what the relationship is anymore. It is complicated but I would never hurt you by trying to make it a romantic one with you just starting out your life, and me towards the end of mine. I am your mentor and benefactor, but I also like young women sometimes. You are not a whore. You just need some help and have been working hard to get it. Sugar Babies and whores don’t clean your house and cook your meals. When you took the job, you described it as a mutually beneficial relationship.
She looked at Richard with a better understanding and said, “I understand. I don’t feel like a whore or Sugar Baby with our arrangement. Just two people helping each other with their needs in a mutually beneficial way. Now that I am not afraid of blow jobs, I have no problem with sucking your cock twice a week. You seemed like you really enjoyed it and that made me feel good too.
Richard smiled and thought to himself that he should have been a psychologist, not a finance major. “Sam, now lay back and spread your legs wide.”
“Mr. Stevens, I will not. I made it very clear I am not going to fuck you.”
“Sam, I am not trying to fuck you, I just want to eat that young delicious pussy of yours.”
Samantha hadn’t even thought of that since guys hadn’t gone down on her in the past, since they weren’t getting any blow jobs from her. She slowly laid back on the bed and spread her legs and closed her eyes.
Richard wasted no time and dove between her legs and attacked her beautiful bald pussy with his tongue, driving Samantha wild.
“Oh, Mr. Stevens, that feels so good. It was worth sucking your dick.” As he lashed her pussy with his tongue, she moaned more and more and clamped her legs around his head. He used an old trick of sticking his finger in her ass, which she did not resist, and she came hard.
“Are you going to do that for me twice a week after I give you a blow job.”
“No.” She looked at him like she had made a bad deal.
“The new deal is you only have to blow me twice a week, but I will lick your pussy any night if you want. It is one of my favorite things to do.”
“I forgive you for being a lecherous old man who tricked an innocent young girl into being his Sugar Baby,” she winked at him.”
“You are not my Sugar Baby. You are a companion, a friend and a nice girl who takes good care of an old man. In every way,” as he winked at her. He meant it this time.
Samantha and Richard got along the next few weeks and she even brought over David, her new boyfriend, to meet him. He played the father role in their meeting, but he really did like him, thought he was a respectful young man and told her so after their meeting. She valued Richard’s opinion, especially about men. David would come over often and Richard was even okay with him staying the night with Samantha.
A couple of weeks later, Richard was getting those mean thoughts again. He wanted to fuck Samantha and he didn’t care why. He wasn’t jealous of David. He just wanted her and didn’t care if she wanted it, but he wasn’t a rapist, so he tried to control himself.
That Saturday night David and a few friends picked her up for a night on the town. He knew they would be drinking and was a little worried. Her friends dropped her off about 4:00am after the bars closed, and Richard was actually waiting up for her like a father would. He helped her up to her room, as she was quite drunk. He helped her take her clothes off and she didn’t even bother to put on her pajamas. She laid in bed naked and he could see her pussy lips were a little red and wet. She probably had some hot sex with David earlier in the evening.
He couldn’t resist his feelings. He took off his clothes and got into bed with her. She was still drunk and thought at first it was David, then realized it was Richard. “Sam, I want to fuck you so bad right now. What would it take for you to let me? I’ll do anything.”
Sam joking replied in a slurry voice, “you would have to stop charging me rent and get a cleaning service.” She was totally joking.
Richard got on top of her and said, “okay great deal, and he lined up his cock against her young tight cunt.”
“Mr. Stevens, I was only kidding about this being a new deal. I am not going to fuck you. Get off me, I don’t want this.”
“Sam, think of how much easier your life would be living here rent free. Besides, you made a deal. In this case a verbal deal is binding.”
He forced her legs open and struggled to get his cock near her already wet pussy. She fought him for a while but finally gave up and he shoved his aching cock into her in one stroke and started thrusting in and out of her.
She cried and beat his back and said, “Mr. Stevens, take it out, you’re being too rough, this is rape.”
“No Sam, you made a great deal. You can’t change your mind. Just enjoy it.”
As he rocked in and out of her slowly, she started to become aroused, especially since David had already given her a good fucking earlier. She started slurring “‘fuck me, fuck me, be my Sugar Daddy.” Richard knew he had finally got what he wanted. A really nice girl who was not cynical and appreciated his help but wanted to help him too. She rolled over on top of him and rode his cock. He then got her on all fours and fucked her harder and harder until they both came with a roar.
The sun was coming up before they finished. Richard looked adoringly at her and said, “Sam, since I am giving you the best deal ever, your services now come with no limit. I am going to fuck you, finger you and lick you whenever I want, in whatever room in the house I want, and you can’t say no. You are going to suck my cock whenever I want too.”
“Mr. Stevens, I don’t know about this. Like they said in the movie ‘you can’t renegotiate the negotiation.’
“Yes Sam, but we didn’t specifically talk about frequency, when you agreed to the deal.”
“Did I mistakenly agree to go from being your Sugar Baby to being your little paid for plaything and fuck toy, and I get to come all the time too and stay here for free?”
“Yes.”
“I think I made a good deal.”
“You made a great deal Sam. So did I.”
Richard and Samantha had a much more comfortable relationship from that point on. She was excited to live in a beautiful house for free and not do household chores anymore, as a housekeeper took over the cleaning and laundry, but she still loved to cook for him. She also got excited being submissive to him, as he would grab her whenever he wanted, bending her over the couch to take her from behind, or sneaking up on her while she was showering and making her get on her knees and suck his cock, while she fingered herself. He also loved to suddenly pull her pajama bottoms down while watching tv together and licking her sweet young cunt until she screamed out with bliss.
He knew though that there was one thing he hadn’t convinced her of and that was anal sex. He knew from their conversations that was ‘off the menu’ of activities, as men had tried it with her, but their dicks wouldn’t fit in her tight butt hole, and they didn’t know that you need to adequately lubricate, and first stretch a woman’s asshole slowly and gently open with your fingers. It had taken Richard years of grooming his late wife for anal sex until she finally relented and gave her most private place to him. Then she loved it and wanted it all the time. As she aged and her vagina became more sensitive from menopause, she actually found it more comfortable than vaginal sex, which was fine with him.
One night when he had Samantha bent over the couch and taking her from behind, he broached the subject. “Sam, I know you have had said you have never had anal sex, and don’t want to because you are afraid of pain, but what it would it take to convince you to try it with me? It would be an honor if you gave me your anal virginity.” He was sincere.
"Mr. Stevens, I already am not paying anything to stay here. I don’t want to feel like one of your young escort girls, so my ass is not for sale.”
“Sam, I am sorry I insulted you.”
“Mr. Stevens, you didn’t insult me. Actually, I just want to tell you that you have been so nice to me and I want to give you my anal virginity.” She wiggled her tight ass cheeks at him and reached back and spread them open and said,” now stick that old cock of yours in there before I change my mind.”
Richard slowly opened up her asshole with his fingers and gently inserted his throbbing member in, drawing it in and out very slowly. Samantha started feeling the strange sensation and a strange feeling climax started building up in her. Her body started shaking and they both cried out as they came in unison.
“Mr. Stevens, what was that?”
“Sam, you just had an anal orgasm. Some women can come during anal sex without even having their clitoris stimulated.”
“Can we have a lot of anal sex?”
“It’s a deal.”
“But part of the deal is someday I may ask you to do me a favor. Just like that line in that famous mob movie.”
“Of course, I remember it Sam. But I hope you don’t ask me someday to shoot someone.”
“No, silly. I am not sure what the favor is, but I just want to have it like an option in a contract.” Samantha was getting really good at business now.
For the next two years of Samantha’s Junior and Senior years completing her degree, Richard and Samantha had great sex whenever they both felt in the mood. There was not a dominant or a submissive role anymore, just great fun between two roommates. She didn’t feel like a Sugar Baby anymore and he didn’t feel like a Sugar Daddy anymore. Samantha got very serious with David and they got engaged, and Richard was thrilled for them. Richard dated women but kept it casual, as he knew he could never replace his wife. Samantha’s father had developed a terminal illness and was not feeling well, so Samantha and David planned a June wedding after graduation in her hometown, and of course Richard would attend.
Samantha came home a day before leaving for the wedding and opened her mail. She was shocked when she opened her student loan statement and the balance showed zero. She found Richard and said, “Mr. Stevens, what do you think happened here, there must be a mistake? I owe a lot of money on my loans.”
“Sam, maybe an anonymous benefactor paid for your loans,” he smiled with a twinkle in his eyes.
“Mr. Stevens, why would you do that? You already did so much for me, and I told you I didn’t want to feel like you were paying me for sex.”
“Sam, this was a combined wedding and graduation gift, as well as a bonus for performing all your wifely duties with such a high degree of excellence. I was never paying you for sex, I was just compensating you for time and companionship, like my escort girls always tell everyone in their ads. You saved me from being lonely and you can’t put a price on that.”
“Mr. Stevens, I can’t believe you did this for me. But understand I am never going to have sex with you again in exchange for services.”
“Sam, I understand your point.”
“No, you misunderstood what I said. From now on I am going to have sex with you because I want to.”
“But Sam, what about David? How is he going to feel about this, since he doesn’t know about us and you are going to be married in a few days?”
“I told him all about us and he is fine with it.”
“Sam, I don’t understand how he could feel fine with you having sex with me, since I was your landlord, I am 64 and you are 22, and we were having sex while he was also having sex with you.”
“Well, I told him all the things you taught me, including loving anal and oral sex, and he is forever thankful to you for turning me into a wanton little slut for him. Sometimes after he comes from one of my superb blow jobs, he says out loud “thank you Mr. Stevens,” knowing that your forcing me to suck you led him to the land of getting my mouth around his cock and his dick in my tight little hole.”
Samantha and David ended up staying in Samantha’s hometown for a few years, as her father’s health declined, and he eventually passed away. Richard dated, developed hobbies and made new friends to fill his time, but he missed Samantha, as well as David, who he had also become very close to.
One day he received a call from Samantha, that her and David were in town to see friends and wanted to come by to see him. They had something important to ask him. He was very excited to see them, but was puzzled what they wanted to tell him?
When they arrived, they all reminisced about old times and caught up with each about their lives. Even though they spoke on the phone the last three years, it was great to meet in person.
“Mr. Stevens. Things have been going great for us. We both got good jobs after getting our degrees and Richard just got a job offer in the city, so we are moving back to this area. I left my job but will get a new one after we settle in here. There is just one problem.”
“What is it?”
“Well, it is a little embarrassing. We are trying to start a family, but David is sterile. We want to find a sperm donor and want it to be you.”
“Samantha, that is no problem. What lab do you want me to go to in order to make the donation?”
“That just seems so clinical to us. We want to do it the natural way. We want you to have sex with me to make a baby.”
Richard turned to David and said,” David, wouldn’t you feel funny about that. I know Sam told you about our relationship, but this would be something different.”
“Mr. Stevens, I would be honored to watch you impregnate our sweet Sam. You did so much for the both of us and are like a grandfather to us. We know you are lonely, and we could move in and pay all your expenses. Maybe you could help watch our baby after it is born, and Sam goes back to work, since you never had children of your own. You might enjoy having a little one around."
“David, let me get this straight. You two want to move in with me. I have sex with Samantha to impregnate her while you sit in the corner and jerk off. Then I become your child’s biological father, grandfather figure and babysitter?”
“Yeah. Remember when Sam said that one day, she might ask you a favor in return for letting you take her up the ass all the time?”
“I would love to honor the deal. I can’t wait for my favorite couple to move in."
David got very excited watching Richard pound his sweet bride into the mattress every night, trying to get her pregnant, while he had his pants down around his ankles jerking off furiously to this beautiful sight. Richard and Samantha had sex in every position you can imagine, but David had also done everything with Samantha that Richard had, so David wasn’t jealous.
One night though while Samantha was riding Richard, and David was looking at her still athletic ass, David realized that Samantha never had a double penetration. He stopped jerking off and got up and slowly walked up to the bed and got onto the bed behind Samantha. Samantha got startled and said, “David I thought we all agreed, we are not having any threesomes. Richard is not comfortable with that.”
Richard stopped pumping Sam and said, “David, what do you have in mind?”
“Mr. Stevens, I want to fuck Sam up the ass while you impregnate her. Is that okay with you?”
“That would be fine with me. I am sure Sam would like to feel so full inside.”
Samantha became angry. “Well it isn’t okay with me. I have my limits and you two aren’t going to make me into a sandwich and hurt me while we are trying to make a baby.”
Richard smiled and pulled Samantha down onto his cock and held her tight. “David, you know sometimes Sam needs some encouragement for new sexual acts. Whether she likes it or night, we are going to be the sandwich and she is going to be the meat."
“Mr. Stevens. David. Don’t you dare!” It was too late though. David got behind Samantha, spread her ass cheeks and plunged into her backside with one swift thrust, as Richard was holding her down onto his cock. She screamed but they wouldn’t stop and started fucking her hard developing a rhythm between them.
Richard decided he needed one more lie and said, “Sam, doing it this way will drive my sperm farther up into you and make it easier for you to get pregnant.”
“Really Mr. Stevens? Oh, I guess this is for the good of me getting pregnant. Please fuck me harder guys. I don’t mind being the lunch meat in a sandwich with my favorite two men.”
The three of them had fun getting Samantha pregnant. Sometimes they doubly penetrated her. Sometimes Richard took her in doggy style while Samantha sucked David’s cock or licked his ass.
After three months Samantha got pregnant. Richard was a little sad because he thought David wouldn’t want him to have sex with his wife anymore after her having the baby.
That weekend, Samantha and Richard were talking, and Richard broached the topic. “Sam, that was a lot of fun we have had getting you pregnant. But I guess now that you are having a child, it will go back to just you and David having sex and I will just be your babysitter?”
“Mr. Stevens, where did you get that idea? You’ve given me a very high sex drive over the years and David travels a lot. He has no issue with us having sex going forward. He is not even sure if he will feel comfortable having sex with me when I start to show. He says it just feels weird to him. Do you feel the same way?"
“No Sam, pregnant women are a big turn on to me. My wife was never able to get pregnant and I always fantasized about having sex with a woman when she is pregnant."
Samantha and Richard continued to have sex while she was pregnant, but only anal sex towards the end, and David would sometimes watch. All were overjoyed when David Jr. was born. When they got home from the hospital Richard asked Samantha if she was going to breastfeed David Jr.
“Yes, I think it is a good thing for the baby, and I have heard it can help you lose your pregnancy weight faster.”
A couple of days later when David was at work Richard saw Samantha breastfeeding the baby and got very turned on. She saw him starting intently at her while her baby suckled at her breast. After she finished and put the baby back in his bassinet, Richard sheepishly looked at her and said, “Sam can I ask you a favor?”
She kiddingly replied, “what do you want me to breastfeed you next?"
“Well actually yes. I never got to see my wife’s breasts fill with milk and always fantasized about sucking them.”
“I’ll gladly feed you ever day, like you fed me for many years, but I have a favor to ask.”
“What is it?”
“Can I now call you Richard instead of Mr. Stevens, since I am 26 years old now!”
“No problem Sam. I would have let you call me Richard when you first moved in when you were 20, but it turned me on that your calling me Mr. Stevens made me feel even older than I was, and you even younger than you were.”
“Richard you really are an old pervert, aren’t you?"
“Sam, you are a pervert too,” he smiled slyly. “You manipulated me into making you my sex toy, convinced me to impregnate you, have had a relationship with me and your husband, and now have made me your boy toy housekeeper baby sitter.”
“Well I guess you taught me well.”
Richard cuddled up with Samantha on the bed and pulled out her swollen breast and sucked the milk slowly out of it, while fingering her gently as she moaned in ecstasy. He stopped and look in her eyes and said, “Sam, who do you think got the better end of the deal with this relationship?”
Samantha looked back at him and said, “I think it was a win, win, win deal for you, David and I.”
Richard lived with Samantha and David as their child grew and he gracefully aged into an old man. Soon after David Jr. turned 18, Richard told them he was sick, and soon after passed away.
At the reading of the will, Samantha and David found out Richard left them everything, including the house and all his investments. They didn’t care about the money though, as they missed him dearly.
There was a note tucked in with the will that said “Samantha and David. I want to thank you for everything you did for me to make my retirement so enjoyable and hope you also enjoyed our years together. I have a favor to ask. A distant cousin of mine has a daughter who is coming to town to attend your college. She is looking for a room to rent. Please consider it. She is a great girl.”
The next week the doorbell rang, and Samantha answered it. Outside stood a beautiful young woman who looked a lot like her. “Hi, sorry to not call first, but my father’s late cousin Richard thought you might be willing to rent me a room while I attend college. I understand you also went to school there.”
“No intrusion. Richard had told us before he passed that you might be contacting us about a room. We would certainly consider it to help you out. What is your name, by the way?”
“My name is Samantha, but you can call me Sam. I am studying medical sports therapy and will be working part time as a massage therapist.”
Samantha’s jaw dropped and she looked at the girl with astonishment and answered, “when can you move in?”
X-MAN215Report