Ray Finds a Partner

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Mum helps panty boy son find family sex.
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Raymond is an only child. His mother Rose and his father had separated when he was five years old so he did not have a father figure as a role model in his life. His mother idolised him when he was little. She loved his blonde hair and allowed it to grow long, onto his shoulders. She'd wanted a daughter, so to satisfy her own fantasies she would often put him into girl's clothes when they were alone in the house together. Raymond accepted this, not knowing any different. At these times she called him Chrissie and over time this became her pet name for him. He suffered a number of illnesses as a young boy so missed a lot of school. The kids teased him about his long hair and teachers would send letters to his mother asking her to have his hair cut shorter. She ignored the letters and moved house frequently in order to change his schools. Raymond was very attached to his mother. They spent all their time together, often because he was truanting from school. He hardly ever played with friends of his own age. In the same way that she idolised him it could be said that he idolised her.

Raymond's mum had schooled him in the facts of life from an early age. They were able to talk openly on every subject without embarrassment. Rose would often tell him dirty jokes as he became a teenager and they would both have a good laugh.

Rose was very strict with him. He learned not to answer back and to do his chores around the house. He would do the hoovering and ironing, make most of the meals and wash up the dishes afterwards. He learned early on that if he challenged Rose's authority she'd put him over her knee for a spanking. The emphasis was on humiliation so often she would ask a friend or neighbour to witness it.

Raymond often became erect whilst lying across his mother's lap but nothing was said about it and he hoped she and the witness had not noticed.

Shortly after his 18th birthday whilst they're sharing a bottle of red wine Rose says to Raymond.

"I expect you must be wanking almost every day now dear, a big strapping young man like you? You don't mind me asking do you dear?"

"Course not mum. Yeah, it's a regular habit. You told me it's natural. Nothing to be ashamed of is it?" Raymond is trying to answer in a matter of fact way. Despite their open relationship his mum is crossing over into very personal territory and he can't help wondering where this is leading. He waits politely for her to continue.

"You've never really had a long term girlfriend have you Chrissie?" Rose says smiling.

"No mum, there've been a few girls but they all seem very silly to me. I get bored with them quickly; mostly though they finish with me after a couple of dates. Do you know why that is mum?" Raymond says, earnestly looking at his mum.

"Well there is something we've not talked about much. Take those jeans off for me for a minute there's a good boy. I've had a look at your computer. I was interested in some of those porn sites you've been looking at."

Raymond's face colours up a little. "I'd rather not mum. Why do you want me to undress?"

"Now, now, Chrissie, you asked me a question. We want to get to the bottom of this don't we dear? You've always let me see you in the bath haven't you? And let me towel you down. Don't argue, do as I say."

Raymond reluctantly removes his jeans revealing that he is wearing ladies panties. His little penis is hard making a tent in the knickers.

"Well Chrissie darling, I can see you've been in my panty drawer again. Do you like the pink satiny ones the best?"

"Yes mummy, I love the feel of them around my cock and balls."

Rose begins to stroke him through the material of the pants. He quickly spurts and his penis subsides.

"Mmmm. That was nice but it's made me feel really horny." Rose says. "It's important for you to learn how to please a woman. Then you'll get them to stay with you. I want to start your training straight away. Quickly now Chrissie dear, kneel down in front of me. Leave your jeans off for now. We can talk while you do me."

Rose pulls over a dining chair and places it in front of him. Within a few seconds she has pulled down her panties, hitched up her skirt and opened her legs wide.

"Don't be shy Chrissie, move closer, you know what I want don't you?"

"I think so mummy, but this will be my first time. Do you mean your cunt Mummy? Did you want me to lick it?" Raymond says. Rose has noticed that his cock is thickening again.

"Yes of course, you've seen those pictures on that website haven't you dear? Pay attention to my clitoris. It's the little bud at the entrance to my cunt. You want to help me out don't you?"

"Yes mummy, I love the way it smells." Without any more hesitation Ray drops his head down between his mum's legs and begins licking delicately, enjoying every second of it.

"Good boy, that's the way. Oh yessss, thank you. I've noticed that your prick may be a bit small for most women. So you might have to find other ways of keeping them happy. Provided you enjoy licking their cunts you may find that girls can overlook your er, deficiencies in other departments. You also need to find one who likes it that you enjoy dressing up in girly clothing. So you just need to hook up with someone who likes panty boys. You are a panty boy aren't you darling?" Rose says, as she enjoys a very satisfying orgasm.

Raymond notices that his penis is once again rock hard. Hearing his mum's assessment of him seems to have made him very excited.

"Yes mummy I am a panty boy. Can I be your panty boy?" he says.

"Well no dear, I think it may be better if you find a wife. But you can of course continue to help me out when I need it, just like you're helping me out right now. You may stop licking my cunt for the time being." Rose pulls up her panties, standing up as she does so.

"On your feet Chrissie, good girl." Rose says pulling the panties he's wearing down to his knees. "Now let's measure you up, mmm, four inches fully erect. You're a bit short aren't you dear?"

"Yes mummy." Raymond looks a little crestfallen.

"Now don't you worry, it's not all that bad when you consider that you're a girly boy."

A few days later Rose and Raymond are sitting watching TV. Rose switches the set off at the end of the programme.

"You've been looking at my legs haven't you Chrissie dear?" she says.

"Yes mummy, you have such lovely legs, I can't help it." His mother is wearing her white towelling robe. It's quite short, showing plenty of leg. Until now she has been sitting demurely with her legs together. Smiling broadly she opens her legs wide, at the same time hitching her robe high up around her bottom. Raymond is surprised to find she is naked under the robe."

"Oh Chrissie, you look surprised. Don't you like my freshly shaved quim? I did it just for you." Rose says. "Now let's have you on your knees, you know what to do don't you?"

"Yes mummy. I don't just like it, I love it." He gets to work, happy to fulfil this duty.

"That's right, good girl, not too rough, suck on the clit. Gently does it. I've been thinking about getting you a suitable partner. There are one or two websites where you can talk on line to women who are looking for someone like yourself. I'm sure that's the best way to go."

Raymond is all in favour but rather nervous about what to say so Rose helps him out with filling in his personal details and photograph. He's good looking with his long blonde hair and soon has started exchanging emails with a number of women. Most of the women are looking for submissive men who are willing to allow them to take the lead. Rose reads the email exchanges and suggests some of the wording for his replies. Photos are exchanged and eventually Rose suggests that one particular woman may make him a good partner.

"But, mum, surely she's way out of my league. Those pictures she's sent me, you've seen them. She's absolutely gorgeous." Raymond says. He's attracted to Betty but can't believe she'd be attracted to him.

"Don't put yourself down Chrissie. You can see she's interested. Why don't you meet up with her and see what happens then? You both need to see each other face to face before you can decide."

It takes a few days but finally a meeting is arranged. Apparently it is usual for couples to meet in a cafe, on neutral ground, at first. But unusually after a number of phone calls have been passing back and forth between Raymond and Betty and also Rose and Betty's mother the first meeting takes place at Rose's home with Betty's mum Celia also invited.

Everything is very relaxed and they all get on well, especially after a few glasses of wine have been consumed. Betty is keen to get some time alone with Raymond so they go outside after Betty explains that she is dying for a cigarette.

"You're not put off because I'm a smoker are you?" Betty says as she lights up. They begin a short walk along the canal.

"Not at all. To be honest I find it sexy." Raymond hopes she hasn't noticed that he's blushing, cursing himself for coming out with a comment like that.

"Do you really?" She stops and looks around checking that no one is nearby. She's a couple of inches taller than him and, facing him, deliberately blows smoke down into his face.

Raymond is already captivated by being close to Betty and feels his erection hardening. Sensing this Betty pushes her body against him then laughs as the erection is obvious through her thin skirt.

"My god, you're not kidding are you?" Betty says, hardly able to speak through her laughter. "I think we are going to get on fine."

Meanwhile back at the house Rose and Celia are sharing a few confidences.

"Betty may be only 22 but she's been around the block a few times." Celia explains. "Her last boyfriend was a swine. She left him because of his drinking and violence. She's hoping to find someone gentler this time."

"She won't have that kind of problem with Raymond, quite the reverse in fact. Has Betty told you he likes to play dress-up?" Rose says, making eye contact with Celia. She feels already that she wants her son to hook up with this family.

"Yes, of course, we tell each other everything." Celia says. "It's a strong reason for her being attracted to Ray. He's a bit younger than Betty. How much experience has he had with women?"

"He's had a few girlfriends but only short term. He's still a virgin as far as I know. I've made sure he knows all about the facts of life. We've always been very close." Rose is a little bit tipsy after the wine. She's not sure how much to tell Celia at this stage. "I'm a single parent, not had a man in my life for years, apart from Raymond that is." Rose can't help smiling and winking at Celia as she says this. "How about you?"

"I brought up Betty mainly on my own. She's had a few uncles, if you know what I mean, and some of them moved in with us for a while. But for the moment it's just the two of us. Men don't seem interested any more. I'm getting too old I guess. But I do miss the sex," Celia says, a little embarrassed. But she feels relaxed with Rose, able to say anything at all.

"That's a shame. If Betty decides she likes my Raymond you never know where things might lead. He's such a good boy, a girly boy." Rose says looking into Celia's eyes again. Celia has no idea what Rose is hinting at but can feel the sexual tension. Her body is responding with arousal.

They hear Betty and Raymond coming back into the house. The two are clearly very relaxed in each other's company so arrangements are made for a further meeting. Rose gives both Celia and Betty a hug and a kiss as they leave. Raymond hesitates, looking for guidance from Rose, whose expression leaves him in no doubt, so he does the same. He kisses Betty full on the lips taking slightly longer than his mother did. Betty responds in kind.

It isn't long before Raymond and Betty are seeing each other almost every day. Rose gets Raymond his first mobile phone and shows him how to send text messages. The two mums encourage them to visit each other-(Betty also now lives with her mother). They live about twenty miles apart so they often stay over if it gets late after the last bus.

The first time this happened was at Celia's house.

"Mrs Slater, sorry but I've missed the last bus. Can you run me home in your car please?" Raymond says looking upset. "We just got carried away talking. I'm ever so sorry."

"I've told you to call me Celia. We don't believe in formalities in this house, do we Betty? Well, no, I can't take you home. I've had a few glasses of wine. Why don't you stay the night? You've had sleepovers before haven't you?"

"No, but I'm sure mum won't mind. It's just..., I've not brought my overnight things." Raymond says, a bit out of his depth. He notices Betty grinning and begins to relax.

"It's lucky you like to wear girly clothes then isn't it?" Celia says winking at Betty. "Betty will sort you out."

"You don't mind if he stays in my room do you mummy? We need to get to know each other better," Betty says, blushing a little. She's thinking that it's about time. Any other man would have fucked her by now. She reminds herself that Ray is different.

"Of course, do what you want with my blessing. I'll make myself scarce if you like. I'll be round at Jane's next door if you want me." Celia says. She puts her shoes and coat on and leaves the house.

Up in Betty's bedroom she decides it's time to take the initiative. "I know it's early dear, but why don't we get ready for bed now. What do you normally wear in bed?"

Ray is not sure how to answer. She knows what he is so it would be stupid to lie. He takes a deep breath. "Well you know from our conversations by email before we met what gets me excited don't you?" He says.

"Yes and I know you're wearing panties right now aren't you?" Betty says, she's seen them peeping out above the top of his trousers.

"Yes I am. Well I've tried different types of nightwear but my favourite is a long nightie." Raymond says looking slightly uncomfortable. "Mum buys them for me."

"You're mum's amazing. I wish my mum understood me as well as yours understands you." Betty says enviously. "Well how about it? Let's change into something comfortable. You can wear one of my long nighties."

Raymond looks a bit hesitant. He knew he'd come to this eventually.

"Don't be shy Ray darling," Betty says. "Take your things off. See, I'm not embarrassed. I'm changing into my nightie. Do you like my underwear dear? I bet you've thought a lot about what I like to wear that you can't see haven't you? See, I wore stockings and suspenders just for you." Betty is now down to her bra and panties. Ray nervously removes his shirt and vest. He stares at Betty lustfully trying to concentrate on what she is saying. He's not told her he is still a virgin. He's scared of what she will think when she realises.

"Oh Betty, you are so good to me. I've wanted to see your underwear ever since I met you." He's trying to pay her a compliment but blushes when he realises how lame that sounds. "Sorry, that came out all wrong. You must think I'm a complete idiot." He removes his jeans. His panties cannot hide his arousal. He looks down, feeling ashamed.

"Mum says I'm a bit small," he says finally.

Betty bursts out laughing. "Try to relax Ray. It's fine. You are fine. You're just what I need right now." She kisses him on the lips, at the same time taking the head of his penis between her finger and thumb. It's still inside the panties. She squeezes it gently. "I can make you come with my hand if you'd like that, but first I want you to do something for me," she says, removing her own panties and sitting, open legged on the bed edge. "Your mum teĺls me you give good head."

Ray smiles. He's suddenly almost back in his comfort zone again. He kneels in front of this gorgeous woman. Betty can't contain herself. She grabs his head in both hands and pulls him roughly down between her legs drawing his nose and mouth into her luxuriant growth of cunt hair. Ray inhales her wonderful cunt smell and begins pleasuring her. He is in heaven. All he wants is Betty's happiness. To his delight he brings her to two glorious and noisy orgasms.

"Well done. Now you know I'm a natural blonde. Your mother was right. She has trained you well. Now let's give you your reward. Drop those panties and sit next to me on the bed. I doubt if this will take very long. You're very stiff aren't you dear?" Betty slips out of her bra. She's naked apart from her black stockings. "You were hoping I'd get my tits out weren't you? Naughty boy. Play with my nipples, that's it." It only takes two pulls on Ray's cock and he spurts all over his legs.

"I came twice, now let's see if you can," says Betty. "Let's find out what turns you on. Your mum has given me one or two ideas. She takes you across her knee for a spanking. You like her doing that don't you? She wants me to spank you if you don't behave. You want me to do that don't you? You're not a proper man are you dear? Tell me what you are whilst I pull on that tiny dick of yours."

This kind of talk is causing stirrings in his subsided member. "I'm a panty boy who likes to dress in women's clothes. It excites me." Ray says feeling waves of shame. " And yes I would like you to spank me if I don't behave. It's more effective for turning me on when there's humiliation involved. That's why having someone else witness the spanking excites me more." Ray's face is crimson as he makes these admissions, his cock as hard as it's ever been.

"So telling you that you're not a proper man and that your dick is too small to satisfy me is also effective isn't it?" Betty says, wanking him. "I can see it's working. I've got plans for you, my darling, plans that involve even more humiliation. I've sent off for a pretty pink maids dress for you to wear when you visit. How would you like to be my maid? And you'd want to serve my mum too all dressed up in frillies wouldn't you dear?"

"Oh, yes, I'd like that." Ray admits, blushing all over again. This time his orgasm takes longer and he has lain back on the bed floundering around hardly able to control his movements. Afterwards Betty lies on top of him and they kiss passionately.

Unexpectedly Celia walks into the room. Betty rolls off Ray but lies on the bed, legs open, not trying to cover herself. "Oh, sorry, I thought you would have heard me come through the front door," Celia says grinning. "I can see you're becoming better acquainted. That didn't take long. It's okay, you don't have to cover up Ray, I've seen it all before. Has Betty found you a pretty nightie for you to sleep in?"

"Yes Mrs Slater, er, I mean Celia. She's sorting me out." Ray feels really embarrassed, more so, as he realises what he has just said.

Betty seems unconcerned. "I thought you'd be out longer mum." She says.

"Yes, well, Jane was out so I went a couple of doors down and had a chat with John, you know who I mean, the old guy who's a bit strange. Couldn't stay too long there but I've had a few gin and tonics." Celia looks towards Raymond then continues. "He stole panties off our washing line last summer. We knew it was him. We didn't bother with the police, he's harmless really. It was fun confronting him about it. It's worked out well really. We've come to an arrangement with him. It benefits John and it benefits us." Celia pauses for a moment thinking she might have said too much.

"You'd better tell him, mum, it's okay." Betty says.

"He never pesters us but whenever there's time and we feel like it we both go round to his house of an evening. He supplies the drinks. We always wear short skirts and show plenty of leg sitting together on his low settee. We gradually let our legs widen apart until he can see our panties. Towards the end of the evening he pays us for the knickers we have been wearing. He's very generous. I got £20 tonight for mine." Celia hauls up her skirt to show that she isn't wearing any underwear. Ray is transfixed by the sight of her cunt as she stands there in the doorway. She makes no attempt to let go of her skirt.

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