SMS: Single Mothers Servicing

She arched her back and cried out as you thrust your cock into her pussy again and again. Your balls slapped off her thighs as you took the single mother from behind, admiring the fine peachy arse before you. You still could not believe how your life had changed to the point where you were now on a bed plowing your cock into a horny mother as part of a local service no less.

Not long ago, you had just moved back to your hometown virtually broke. After graduating, you had tried for years to live and work in the city where you had attended university, wishing to stay with the friends you had made there. Somehow, though, you just couldn’t hack it. You ended up drifting from job to job, always seeming to fail for one reason or another, as did your relationships.

Everyone else moved on, yet you found yourself trapped, and eventually you had but to return home. Fortunately, your elder sister Jane had a spare room that she was able to offer you, and you move in with her and her family. Jane lived in a small housing estate where many other families lived, some of whom were friends of your sister since childhood and others who had become friends of hers as their kids attended the same school. This included a large number of single mothers, who had come together to form their own social group. This group included your sister’s friend Jade, a sarcastic chain-smoking 40 year old with short black hair, Emma, the sporty blonde in her 30s who was always keen on keeping shape, and Caitlyn the chubby little redhead amongst others.

You had found it difficult to find work, and with no social life of your own there you agreed to babysit the children of your sister Jane’s single friends’ kids every now and again, usually Jade’s, so that they could go out in return for being given the room by your sister and for a bit of pocket money from the parent of the kids you babysat. The fact that they even called it pocket money and that you were working as a babysitter naturally did not help with your self-confidence at the time, but it would lead on to other things.

It was while babysitting Jade’s two kids at her home that it all started. Jade had gone out with your sister and their friends from work for the night. Her kids had gone to bed finally and you were taking advantage of Jade’s wifi with your laptop and her open bar policy with a glass of her cider. Quickly swapping browser tabs and pulling your hand out your pants when you heard the door open, you look up innocently to see Jade leaning against the doorway, clearly tipsy but still with it, a fag in one hand as she looked at you with a scowl. She was dressed in her clubbing outfit, a black leather skirt with an off the shoulder black top and high heeled boots that give a couple of extra inches to her 5’4 frame. While not skinny, Jade was well toned from a busy life, her breasts either still perky or well-supported by her bra. Her black hair was cut short in a choppy style while her brown eyes still had an intensity to them.

“Hello sexy,” she says cheekily, before coming in, shutting the door behind her and throwing herself onto the settee next to you. “Good night?” you ask, and she throws you a look. “Typical night, lots of drinking, frustration, and coming home alone while the rest... forget it, pour me a glass.” You go get her a glass while she digs out a twenty that she gives you on your return for the night. Your sister’s is only a couple of houses away, so you only got a short walk to go. You start to pack your laptop away but Jade stops you. “No rush, might as well finish your drink,” she tells you, so you dump the bag back down and, picking back up your glass, sit back down next to her.

“It’s nice to have company, even if it is the babysitter,” she moans. You’re used to her talking about you like that so you take no offense. “The others, including your sister, don’t know how lucky they are to have people to go home to, not that I would have time for dating nor do I really want to have to deal with a relationship anyway, can’t be arsed with all that now. Just need to get under someone. Oh, sorry, I shouldn’t talk like that to you, I’m not making you awkward am I?”

“No, no, it’s fine,” you reply awkwardly. Even if you did find it easy to talk to women you doubt you would have been finding this comfortable.

“I guess you understand, I doubt you have got your dick wet in a while, what with how things are. Heh, I guess what I really want is a babysitter for me than the kids, one to look after me.”

You don’t know what to say to that so you just sip your wine, though in your head you think, wouldn’t that be a male prostitute? You notice that Jade has stopped talking, and glancing over at her you realise she is sat there on the settee staring at you with a weird look.

“Would you ever consider doing something like that, John?” she asks you, a rather intense tone to her voice.

“What do you mean?”

“Exactly what I said, would you consider doing what a woman told you to, providing ‘services’ to someone in return for money.” A faraway look crosses Jade’s face. “It would be clear what kind of night it would be, there wouldn’t be any misunderstandings, you’d both know what it was, and she would get to have what she wanted. No strings attached.”

You are not sure how to respond, but then Jade suddenly pulls out her purse. Rummaging through, she takes out and counts some notes.

“Let’s just say, as a joke, I was to offer you, ummmm, forty two, what would you say?”

Jade fingers the money thoughtfully, a predatory smirk on her face. “And what would you say if it wasn’t a joke?” Her face takes on a more serious look. “Would you do it, knowing it was just for tonight, and under my terms?”