Mary had an unassuming appearance. An almost pretty face and loose clothing concealed her considerable inherent sexuality. Her mother’s Polynesian heritage gave her that golden skin color and long black hair. It was what was inside that mattered most and she had that very well covered.
Her experienced vagina worked magic on any invited cock. Skilled foreplay of all kinds made any encounter memorable. Many mild fetishes were in her repertoire and could be enjoyed when requested. The most important sex organ is inside the skull, and Mary’s mind was full of sex. She was still eager for more of it, especially in her mid-thirties.
Mary had discovered sex quite young. Her youthful first partners left something lacking so she moved up the age range until she found some men that hit the spot properly. That also speeded up her knowledge acquisition because they showed her new things that naked bodies could enjoy.
Her first husband was a boyfriend who fussed over her so much that she agreed to marry him. That was ten years ago. Two years later he was arrested and sent to jail on some old warrants. They divorced so she had no means of support.
A gal she knew hooked her up with an escort agency. Her body had matured to nice gentle curves below her 38D bosom. After her interview fuck, the boss put her in the premium ranks and her income from working only four nights a week was surprising. She truly enjoyed her clients and built a stable of regulars who tipped very well. Several of them qualified for bareback too. She always loved the feeling of semen sprayed deep.
Mary liked the sex but felt unfulfilled in other ways. All the dressing up and fancy meals just weren’t like her real self. Plus, she struggled with her weight. When her favorite client, Maynard, asked her to marry him she took it seriously.
She did have some questions, “My dear man, I like you a lot but I’m not sure it is love. Could we live together and you pay me what I’m earning now so I don’t get hurt if it doesn’t work out? Then there is the issue of sex. I’m used to more than you might be able to provide. You are twenty years older than me, after all. You think on these issues and we will talk again on your next appointment.” He agreed.
Mary gave him a big kiss the next morning when she left. Two big differences – she usually didn’t kiss or stay overnight with clients. But this was special.
Two nights later they were naked together again. She hadn’t had a client in between so she insisted on a good fuck before they talked. Didn’t want hornies to influence judgement. Then she opened with, “What have you come up with, Mr. Maynard?” She had a Southern upbringing and addressed every naked man semi-formally.
He replied, caressing a firm breast and tweaking a nipple to make it stand up, “I think we can be very good for each other, which is an important kind of love. I understand your concern about sex. Perhaps continuing escorting, but less frequently, would take care of that. I’ve been sharing you for more than a year now, so it would be nothing new. I have enough money to make up the difference in your income as well, so that’s not a problem. When would you like to move in?”
Mary thought for a moment and said, “Probably next weekend. I’ll talk with my agency and my landlord in the meantime. I’m booked with some regulars like you quite a way out but won’t take any new clients. I’ll adjust as we get settled in together.”
Maynard added, “I’ll arrange for the belongings you don’t bring along to be stored for the time being. OK?”
Mary nodded and kissed him. Her hands had brought him to his full hardness again as they talked so she straddled her new housemate and engulfed him quickly. She knew he favored this position so her tits could provide stimulation for both of them. She never tired of playful hands or sucking lips on them. Her cunt worked him to ejaculation then she had to shower and leave.
She had a second client that night, a relatively unusual occurrence. As this second man entered her pussy, Mary thought about Maynard. That was another unusual thing since she was pretty good at focusing on whoever she was with. This guy was a new client so wore a condom and didn’t want to eat her pussy, so wasn’t aware she’d been laid earlier that evening. She’d never do him again anyway. There were enough regulars to meet her needs.
On the third night in a row in Maynard’s familiar bed, Mary realized how much she’d missed having someone to snuggle with in the night. There was another surprise too. It wasn’t that Maynard wanted sex each night, but how it was different than when he was a client.
She’d had a date with a regular who she did bareback. When she got home she usually showered but Maynard led her directly to the bedroom and stripped her. He headed towards the Y so she protested but he said “I know what I’m doing. You did bareback earlier, right?” She nodded.
He tasted her pussy a little, tickling her clit for a short time before burying his rod into the client’s remaining juices. As they both enjoyed his slamming strokes in her slippery snatch he said, “Tell me about the man you just fucked.”
They both got more aroused as they moved in synchrony with her narration. They were both breathing hard when they finished. After a bit Mary commented, “Wow. That got you going!”
Maynard smiled and said, “That brought back some good memories. I’d only been married a short time when I found out my new bride had been regularly screwing a boyfriend from before she met me right up until the wedding. I was mad at first, but as I dwelled on it I got turned on by the thoughts. Then I insisted she go fuck him with me knowing about it and come right home. It was hot and we banged like bunnies. After about four times she wouldn’t do it anymore, so just the memories were used from time to time.
“About fifteen years later she ran into him again. Our sex life needed a jump-start so she agreed to fuck him. It worked and they screwed just about every week for six months until he moved away. So that’s why I’m OK with what you are doing.”
Mary held him close, “I’m glad I can give you such a special pleasure. Of course I enjoyed the guy before you. I guess fucking him was just foreplay for our lovemaking. You are so good to me and I’ll do anything you want.”
Mary was tiring of escorting. Not the sex, just the hassle of arrangements and the general atmosphere. Maynard had a suggestion. He knew other single guys who really needed help keeping house and probably needed pussy too. Mary enjoyed housecleaning in the nude and he knew her clients would love it.
They worked out a business plan with pricing that included nude housecleaning at one rate and a half hour of “personal services” at a higher cost. They were much less than her escort rates because money wasn’t the object and she wanted to be affordable to men who would need and appreciate her. She would visit a client no more than twice a week although occasional special help like setting up for party could be arranged. Medical clearance was important too for some of the services. And, of course, complete confidentiality.
Maynard was her marketing person and checked out any prospects. He wanted her to be safe and happy.
Mary went to see her first client with a bit of apprehension, mostly because this was a new situation. Rodney was a trim man in his late forties who watched with delight as she bounced around cleaning up his place. He was happy to show her where things were that she needed or had to put away. At the end she could sense that he wasn’t ready for sex so she gave him a complimentary blow job as he cupped her tits. Maynard got laid promptly when she got home.
Her next client, Kerry, was a decade younger than she was. His sex indicator was full on when she finished the basics so she sat down on it while he was in his desk chair. He put three loads in her during the half-hour they coupled. He worked at home and had very little social life. Maynard got very wet pussy at home that day and he loved it.
Hernando was seventy, somewhat heavyset, and Hispanic. He was shy so it was the second visit that got the special services going full bore. He was well equipped with big hairy balls that hung and swung. They tickled her ass as they slapped against it in the missionary position. He knew how to use his big brown dick so Maynard didn’t have to be concerned about any climax but his own when a well-fucked Mary returned on those days. He reclaimed his girlfriend quickly and they made love again later that night.
Mary was delighted with this arrangement. She got lots of physical exercise from her cleaning, brought in money, and had sex with three different age groups. Each client got her twice a week with Sunday being only for Maynard. The regular contact meant she really got to know her clients and what they liked, so her services were superb.
It was not all routine. While Kerry and Hernando were content with variations on regular fucking, Rodney had imagination. It didn’t surface until he got comfortable with Mary. He was introspective and shy. But when he did open up they explored a bunch of fetishes. He asked for more “special” time and Maynard figured it was OK as long as Mary was having fun. She did, and would give her boyfriend a rerun of the especially interesting things. With his imagination and her experience, there were plenty of variations of bondage, submission, watersports, and such that they could have fun with.
One surprise was the request that she train Rodney’s eighteen-year-old son how to be a good fucker. The boy was shy like his dad and had little experience. Mary said OK and one hour a week was scheduled for his lessons. Dad would get his own special services after the son left.
Mary gave Dad an agenda of topics that he had to go over with his offspring. Law, biology, contraception, and psychology were the main topics. After some of those were covered, Mary would start on the practical parts.
This had happened before in her escorting so she knew what to expect and do. What she didn’t expect was how shy Colin was. The first hour they just talked. She had to lead him every step of the way. Seduction was not getting its normal response so she finally put on her dominatrix “hat”. He was just so submissive that she’d simply have to take charge.
Wearing only a robe herself, she ordered him to strip right in front of her. He hurried to comply and his pecker head was already near his belly button. So far so good. She opened her robe and ordered, “Hold my right tit and suck on it.” After a few minutes, “Good. Now the left one.” She ordered him to do some very specific things to them for a while. Before that was finished she felt and smelled semen splashing on her belly. He’d ejaculated without even being touched.
Wiping it off with a towel and no comment, Mary laid back and pulled his face to her cunt. She kept directing him with comments like, “Lick it”, “Suck on my love lips”, “Stick your tongue in where I like cocks to go”, “Find the hole where my pee comes out with your tongue”, and “Suck on my love bud.” He had orders to warn her if he was going to shoot semen again.
He finally indicated that the explosion was imminent so she pulled his pecker up to her mouth and took the shot there. “Mmmm. Your juice tastes as good as your father’s,” thus reminding him that he was sharing this woman.
That was enough for one day. She fucked her pupil’s eager father as she filled him in on the progress. He expressed thoughts about her dominating him too. The astute teacher picked up on that.
In the next session, Mary opened her pleasure portal in the classic position to invite her student’s virginal plunge. What happened next she wasn’t expecting. He asked her for “doggy please” and fumbled a bit before the embedding stroke. He then began slamming into her deeply and rapidly. She soon felt him spurt cum but he didn’t stop. Many more thrusts before she felt it again. He still kept pumping. She just braced herself. It wasn’t bad but it wasn’t doing enough for her own orgasm.
If her partner would reach around and stimulate her swinging tits it would help, but this youngster just held her hips and fucked away. She could hear his labored breathing and feel his body sweat with exertion. He finally rolled off and collapsed on the bed without cumming again. When he could speak he asked weakly, “Was I good?”
Mary was lying beside him. She gave him a quick kiss and asked, “Where did you learn to fuck like that?” dodging the question.
“That’s what I see on the internet that older women like,” was the reply.
Mary was touched by his sincere attempt to please. “I liked what you did. Let’s rest a bit and I’ll show you some things you need to know.” A few sessions later he realized what had happened and they laughed about it. Mary said truthfully that she’d never forget his first lay!
At Colin’s final training session, Mary arranged for his father to secretly watch his son’s copulation with her. Afterwards, naked with her as usual, Rodney asked Mary to be his wife, knowing full well she was living with Maynard.
The wise woman had sensed Rodney’s growing feelings so was prepared for a gentle answer. “Rodney, I care for you a lot, and for your son also. But I care for the other men who are my clients too. My love is reserved for Maynard though. It’s time for you to have a girlfriend. One who would like to sleep with your son as well would be ideal. I’ll work on that but if you find any candidates I’d be glad to check them out. OK?” Rodney gave her a big flood of semen and an equivalent tip.
Mary knew a divorced woman near Rodney’s age at church that she thought might be receptive. The demand for Mary’s special brand of service was more than she could keep up with. She passed along any prospects she didn’t want to handle herself.
Veronica already had one cleaning client via Mary and was ready for another. Mary invited her over for drinks one evening after they both had serviced clients. After a few drinks Mary broached the subject of Rodney and his son. After they talked a bit Veronica agreed to be introduced.
Veronica said, “What can I do to thank you for being so helpful?”
Mary thought for a bit and replied, “Would you help me give Maynard a surprise treat?”
“Sure, you name it!”
When Maynard returned a short time later he called for Mary. “In here sweetie,” came the reply from the bedroom. He walked in and stopped in amazement. On their bed were two naked women with beckoning furry fun places pointed right at him. He wasted no time getting his own body naked between them and started exploring the new slim and small titted treasure that Mary had brought him. He rose to the challenge and all three enjoyed the occasion.
The meeting between Veronica and Rodney and his son went very well and her work start date was arranged. It was set a couple of weeks out because Mary advised both of them to consider any sex as personal and not work related. They needed to date several times to make sure that was good before the work arrangement was started.
That went well. Veronica reported she bedded Rodney on the first date and thanked Mary for training Colin who she enjoyed for the first time just this week. And yes, Rodney was fine with her work sex just as he had been with Mary’s. A finale threesome with father and son was arranged for Mary.
Before we leave that developing relationship on its path, there was one other thing. Veronica asked Mary’s advice regarding her seventeen-year-old virgin daughter Suzy who was ready to become sexually active. Would it be better to have Rodney initiate Suzy or Colin?
Mary suggested the young woman spend time with each before she herself made that decision but Colin was quite capable now of making it a good experience and he was her peer. Did she know her mother was screwing him? That needed to be openly discussed with the options that Veronica cut Colin off or her daughter could also couple with Rodney. The first choice was much simpler for now. Colin was chosen and Veronica stopped screwing him.
Suzy later thanked Mary for training Colin so well. “My first time was so much better than my girlfriends have reported. He helped me get really relaxed by gently exploring my body and having me touch his all over, then suck on any part I wanted to. Then he teased my nipples and pussy with his tongue and I thought I’d go crazy with pleasure. When he finally stretched my vagina with his big pecker I was so ready that I came on the first stroke. Wow! And later too when his hot juice flooded me. I wouldn’t let him loose and fucked him again in just a little while. Now I know what the fuss is all about. Thank you! Thank you!”
Mary had to talk to her main man. Half of her sex partners were gone. The only remaining client was the elderly Hernando. No young stuff left. After a good fuck Mary looked very serious, “Maynard, I need to make a big decision and I want your input. For the first time in quite a while I don’t have any younger lovers. I’m very happy with you as my main partner so maybe it’s time I slowed down my outside sex. Do I look for younger cock or not?”
Maynard held her cheeks and gave her a fervent kiss. “You are by far the best thing that has happened to me in my life. I’ve never told you that many decades ago I read a book titled ‘The Happy Hooker’ by a Dutch prostitute. I loved her attitude about enjoying sex and hoped I’d someday find a woman like that. You are that person and I’m delighted. I love you. Please don’t change!”
Mary started to cry, “I’m not a hooker any more but I am a whore. You know that I am fine with who I am and what I do. It means a lot to me that you not only like that but don’t want me to stop. I will marry you if the offer is still open.”
It was a small private wedding. The honeymoon at a nice resort was true to form. Maynard asked for, and got to watch, Mary bang the brains, and lots of cum, out of a pair of teenage brothers who had ogled her at the pool.
A few weeks later Rodney called Mary and asked if she was accepting new clients. His older son was getting divorced and moving to his own apartment. Was she interested? She’d go meet him.
The talking part interview went well. Derek was devastated that his wife of two years had left him for another man. She had insisted on being a virgin at their wedding and sex, starting with the wedding night, had never been comfortable for her because of his penis size. Plus, he had a low sperm count and she wanted lots of kids. She’d been secretly fucking a smaller-dicked divorced guy with several kids so when she got pregnant by him she split.
Mary hugged him as he spilled out his sad tale. She understood why he didn’t want much to do with women. She could be the perfect answer to rebuild his ego and relieve his hornies.
“I’d like to work with you,” she started. “Did your father tell you about my special services?” He nodded. “Would you like a free sample?” His face brightened the most she had seen so far. He was very nice looking when he smiled.
She had him stand up and dropped his jeans. His floppy dick soon rose to an impressive height and her hand couldn’t go around it. She sat him on an armless chair, quickly stripped, and planted a nipple in his mouth while lining up her already lubricated snatch. Oh, he stretched her SOOO nicely! She didn’t have to expend much energy before this neglected male organ spewed big pulses of semen inside her.
She sat back and had him fondle her breasts as she diddled herself to a climax. “I think you need my services two or three days a week. Tell me which and I’ll give you a price.” They settled on three times, to Mary’s delight. She’d offered a quantity discount hoping he would take it. She was very pleased he did, and not for the money. Maynard would enjoy the stretched and semen soaked pussy she’d offer when she got home today and after each visit. She would have lots of fun getting it that way!
Derek progressed rapidly. Mary had well developed vaginal muscles so the frequent stretching by his large schlong didn’t impact her couplings with Maynard or Hernando. She especially liked being on top so she could watch his face while he played with her tits and pussy as she rose and fell on his swollen tool. She honestly exclaimed how good it felt and how he filled her so well. His self-image loved it.
At the end of the first week Rodney called Mary to get her take on his son. He could hear her smiling with her compliments and thankyous for setting them up. She asked, “I take it you haven’t told him that I’ve fucked you and Colin.”
“No I haven’t. Figured that was TMI and you’d want to handle that.”
“Good call. How’s Veronica doing?”
“We’re having a great time and our children are banging each other’s brains out. Sure got them away from their smartphones! Suzy’s a hottie like her mother and loves running around the house naked with cum running down her thighs. She knows Colin has fucked her mom and she’s giving strong signals that she wants my cock too.”
“Like what?” asked Mary.
“Like getting in the shower with me and wanting to wash each other. Like sitting in my lap when I am naked and rubbing Colin’s cum on my rod in a slider. I had to resist letting it pop up inside her cunt.”
“Why didn’t you?”
Rodney sighed, “We need to have a family conference so all is out in the open. Of course, I’d love to screw such a young beauty. But don’t want any repercussions.”
“Let me know what happens!”
They talked and Rodney was promptly embedded in a seventeen-year-old hot pussy. When her mom was out at her client, Suzy shuttled between father and son until both were thoroughly drained. The third time that happened, Rodney figured this chick was a sensation-seeker so he took her and Colin into the bathroom. “Lay down in the tub and spread your legs!” he ordered the girl. She looked at him quizzically and complied. “Colin, help me out!”
He stood between her feet and let loose a strong stream of piss right at her cunt. She yelped at the first contact then began laughing as it tickled her clit and sensitive tissues. Colin joined in from the side. Before they finished she was spraying Rodney’s feet and shins. When Rodney finished he sat her up and she took his dick into her mouth and cleaned off the dribbles. Same for Colin.
Suzy looked at the two guys and blurted, “Wow. I feel SOOO wicked and I love it. Let’s do that again!”
They each put a couple of beers down and before long were back in the bathroom. Colin was hard again so Suzy sat on his pecker in the tub while Dad pissed on their parts as they fucked. Damn, pissing on his own son’s dick was wild. When Colin got his rocks off and could aim his hose again they traded places. That’s when Veronica walked in.
She shrieked in surprise, quickly stripped, and took Colin’s place as soon as he finished. She was shaking with excitement as she sprayed her boyfriend’s pecker as it went in and out of her daughter’s snatch.
Suzy came big time from the combination of Rodney’s big box filler and her own mother’s pee stimulation. She shook and almost bounced off of Rodney who was desperately slamming from below to get his own nut. He just barely started squirting when Veronica ran out of ammo and splashed several big globs of cream in the young woman.
All four crowded into the shower and laughed like crazy as they rinsed off. Everyone needed a nap after all that energy was expended.
Meanwhile Mary was working for, and with, Derek. She was showing him ways to fuck he’d never seen before. Enthusiastic guys always made her feel good all over. She was waiting for an opportunity to tell him about her history with his family when he provided it.
He hadn’t knowingly shared a woman before. His wife was cheating and when he found out he stopped screwing her. But this was different.
“Mary, did you work for my dad? Is that how he knew to introduce us?”
Derek paused his stroking deep inside her. “So he’s been in here too?”
“Yes, many times.”
Derek continued, stroking slowly, “And what about Colin?”
Mary squeezed his embedded pecker as she answered, “I was his first piece and taught him how to screw.”
Derek slammed into her several times very hard and shot his wad.
Hugging him, Mary said, “I’m glad you know now. I don’t like secrets, especially in families. Any more questions?”
Derek shook his head and wordlessly kept fucking until he blasted another load of semen deep in this amazing woman, right where his dad and brother had also. A rather primitive male bonding, he thought.
The watersports incident had brought something to the surface in young Suzy. She seemed to never get enough screwing but began to realize it was more than the physical pleasure that she sought. The wickedness of the pee play including her own mother clued her in that the psychology of sex was the most fascinating part. Banging a father and son, both of whom also regularly stuck the same cocks in the birth canal she had entered life from, was a huge turn on.
She began probing the sexual experiences of her two lovers as they screwed. They provided vicarious thrills. But then she wanted more adventures of her own. She approached her mother.