Shirley has An Adventure Ch. 02

I was pleased about my boyfriend's reaction and wanted to let Raymond know straight away. Charles dropped me off at home kissing me goodbye and I went inside the house. I idly speculated on what the neighbours must think about my naughty behaviour but wasn't too bothered. They can think what they like.

It was the middle of the afternoon so I sent Raymond a text.

"I've good news for you. Don't be late home sweetie. xx"

Of course, Raymond rang me as soon as he was free to do so.

"What is it, Shirley? I'm dying to know."

"Just something that cropped up in conversation with Charles when we were in bed together. We can talk about it tonight."

"Give me a hint please. Don't keep me in suspense."

"No hints sweetie. I like to keep you in suspenders." I giggled, hoping I hadn't given the game away.

"Okay, sweetheart. Love you. See you later."

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"......and then he told me to turn over and fucked me from behind."

"What! You didn't let him..."

"No, don't be silly, you know how I hate that."

I couldn't contain myself and had given him full disclosure as soon as he walked through the door.

Later, in bed, Raymond moved down the bed and licked me until I flushed without me asking. I took his cock in my hand whilst we talked about our future trip to Charles' house on Saturday night. I was stroking him using a pair of his panties. I could see he was not far off spurting when he said;

"I'm not sure I want him to go in my bum, do you think he'll be offended if I say "No"?"

"No, Charles won't be offended one bit. I'll talk to him about it. But I'll bet you'd be happy to suck him off, wouldn't you?"

"I'd certainly like to give that a try." He spurted copiously and I managed to catch it all in the panties.

We decided Raymond would become Diana when we called at Charles' house on Saturday. He refused to go there dressed so we took an overnight bag with what he needed. Raymond is quite shy but when he's determined to do something he'll carry it through. I could tell he was very nervous as we arrived but I'd primed Charles beforehand, so in his kind, sensitive way he took Raymond into his bedroom with the bag and left him to sort himself out. I waited for a few minutes then joined my hubby to help him with makeup and the wig.

"You look wonderful Raymond, I'm so proud of you. I'll go downstairs and announce you as we agreed so follow me down and come in when I've said the words."

"You've got a new visitor. Here she is, meet my friend Diana." I said.

"Hello Diana." Charles said with a serious expression. Fortunately, I was standing behind my hubby so he couldn't see me grinning. Charles greeted Diana with a kiss on both cheeks, still keeping his face straight. "I'm delighted to meet you." He added. "Can I get you a glass of wine? Shirley and I have already started drinking."

"Thank you." He/she said timidly. His masculine voice rather spoiled the effect although he'd attempted to move it up an octave.

I think we were all feeling awkward so the drink helped us to relax. We all swallowed three glasses in quick succession as we tried to behave as if there was nothing unusual going on. I raised my skirt a few inches and opened my legs wide. I was sitting next to my hubby on the sofa so Charles, who was opposite in the chair, had a good view up my skirt. I noticed his eyebrows raise in surprise. In honour of the occasion, I'd not put on any panties and he could see my newly shaved pussy.

"Well, well, Shirley, that is a surprise. Show your friend Diana what you are showing me. Don't be shy. Pull up your skirt, I'm sure she'd like to see as well."

I raised my skirt as requested. Raymond had never seen me shaved. I knew my hubby was very unsure of himself and hoped my bare pudenda would take his mind off his first experience of being a woman.

"What a lovely view, Shirley. I think it's time we reciprocated don't you Diana?" Charles said. "I don't mind going first or would you prefer to show us what you've got under that pretty skirt."

Diana blushed, looking flustered, I looked her way and nodded my head looking stern. I knew that once she'd been naughty for him, flashing her knickers and stocking tops she'd relax.

Slowly her legs drifted open and she slid her skirt a bit higher. I was sure Charles could see the bulge in her panties.

Almost immediately Charles stood up, pulled down his jeans and underpants and kicked them off. He looked a bit silly standing there with his shirt lap dangling behind him, but appeared not self conscious at all.

"Now we are all showing ourselves off we can relax, can't we? I had no idea you had such beautiful legs, Diana. Aren't I lucky to have two gorgeous women to entertain?"

His penis was thickening but not fully erect. "Let's get more comfortable." He stood between the two of us and prepared to sit in between, his bare bottom sticking out. "Budge along a bit, I'm sure there's room for three of us on this sofa."

We obliged him; our skirts still high up our legs. Our bodies were touching and I felt hot, I wanted to stroke Charles' cock but thought I'd better let Charles take the lead. He'd turned to Diana and was stroking her leg.

"Have you ever kissed a man, Diana?" He said.

"No, sir."

"How about trying it now."

Charles put his arm around her and kissed her on the lips briefly, no tongues.

He then turned to me and kissed me passionately. Our tongues entwined inside his mouth. I began to stroke his cock; I couldn't help it. He didn't push me away.

"I'm going to fuck Shirley in a minute, you won't get jealous, will you?"

"Maybe a little bit, but I like her having affairs. I want her to experience new things. And I like you."

"Thank you. Before we do it, I'd like you to touch my cock. Can you do that for me?"

"Okay."

"Shirley, leave go, for a minute." I did it as he was speaking.

Diana took the phallus between her thumb and index finger and began stroking it up and down. It grew bigger in her hand.

"Have you imagined doing this when you've played with your clitoris."

"Yes, sir."

"Do you like it?"

"Yeah, it makes me feel nice."

"Good girl, would you go one step further and give it a big kiss?"

Diana, now very aroused, knelt in front of Charles and kissed the tip lovingly.

"Take it in your mouth and make it big for Shirley. As you know she loves big cocks."

She didn't hesitate, opening her mouth wide. It was her first time doing anything with a man. She'd read a lot about sissies sucking cock. She told me afterwards that it was a bit like losing her virginity. I'd said 'No' buggery would be your virginity. Then I had to explain to her what buggery meant.

"I just thought it was a swear word!" she'd said.

Charles obviously enjoyed Diana's licking and slurping. His cock was now up to full size. Diana was taking more and more of the monster down her throat. We could see her Adam's apple working.

"Thank you my dear, if you don't stop soon, I'm going to squirt and I'd rather save that for your wife. You've done an excellent job."

Reluctantly my hubby began to slow down and gradually withdrew, giving it a final kiss after it popped out.

I was very aroused watching Diana, my cunt juices flowing freely. Part of it was knowing what was to come but most of all it was seeing my hubby on his knees dressed as a woman sucking cock. I loved it. I took Charles by the hand and led him towards the stairs.

"Let's go to bed darling. Diana, follow on. You can find out how a real man does it." I said.

I wasn't being cruel because I knew my hubby would enjoy the words and it would increase his arousal. As Sissy Diana he knew he/she couldn't pretend to be the alpha male. That was Charles' job.

Sure enough, as Charles gave me a thorough fucking using all the different positions we loved so much I spotted my sissy with her panties around her ankles masturbating furiously.

We took a taxi home, Raymond now wearing men's clothes again.

It was clear that Raymond had enjoyed himself. In his eyes Charles was perfect. He couldn't wait for the next Saturday.

A few days later under instruction from Charles who had given me a couple of items to use with Raymond when we were in bed together, I began giving Raymond some experiences of anal play.

It started with the lube.

"Turn away from me sweetie. I just want to try something. It's okay darling, it won't hurt. I began by squirting the lube up his bottom.

My index finger poked into his back door.

"Ooo. I like that." Raymond said. I noticed his cock thickening.

"Good girl, just relax. I'm going to try something bigger." I extract my finger replacing it with the lube covered dildo that Charles gave me until it popped in.

"What's that?"

"It's a dildo Raymond. I'd like you to keep it in whilst we play together tonight. How does it feel?"

"It's okay. But I said I didn't want that er, buggery thing."

"Don't worry sweetie, you don't have to do anything you don't want to do. But look at your clittie, love. It's nice and stiff isn't it?"

"Yeah, it's swollen. I didn't expect that."

"Let me try something."

I took hold of the dildo, moving it around, in and out a little. His cock jerked and strained, if anything growing bigger. Raymond likes me to call it a clitoris, it makes him feel more girlie.

"Your clit is almost ready to squirt. Do you want to fuck me with it?"

"Can I?"

"Of course, but keep the dildo in, good girl."

We did it missionary style for a change, Raymond usually likes me to be on top. I could see he was trying to think of other things hoping he could last longer so I didn't make a sound. Naturally he didn't last very long and I didn't have a fall. I put my hand on the top of his head and pushed down a tiny bit. Raymond, bless him, understood and probably would have done it without a prompt. He brought me off with his tongue like the good girl he is becoming.

"Do you want me to keep the dildo in?"

"Why not? But if it keeps you awake you have my permission to pull it out sweetie."

"Thanks, I will." A pause, then "Shirley?"

"Yes dear?"

"Do you want me to do the buggery thing?"

"No darling, it's entirely up to you. It's just, some people call it a man-pussy. Some wives put on a strap on dildo and fuck their husbands with it. Would you like me to do that?"

I could see Raymond thinking about it.

"Maybe. But I'll have to give it more thought."

"Shirley?"

"Yes dear?"

"Now it's so warm at night, can I start wearing proper thin silky women's nighties in bed?"

"Of course you can sweetie. If you like we can talk to our doctor about some hormone treatment. It'll help you grow little breasts. You'd look good with a pair of titties wouldn't you?"

I felt down the bed, his cock was fully erect again. He didn't answer, but obviously the idea excited him.

Saturday came round again, following a similar pattern to the previous week. Diana was becoming more accomplished at cock sucking. Charles allowed her to suck him until he spurted. Some of it Diana swallowed, some went on her face and down her dress.

All three of us stripped naked and got into bed together. I'd brought a strap on dildo with me. I'd bought it from the local sex shop in town. It was a new experience and I was very nervous but the woman behind the counter smiled at me and put me at my ease. I'd wondered if my hubby would be interested. Charles was all for it. He'd fully accepted Raymond's reluctance about anal penetration by him and had no intention of putting any pressure on him.

I got out of the bed and put the strap on around my waist. It had a small protuberance on the inside which came into contact with my clitoris providing stimulation for me.

"Do you want to give this a try Diana dear?" I said.

She blushed, looked uncertain, then nodded her head. Why this should be okay when buggery by Charles wasn't I don't know.

Whilst Charles was recovering from squirting into Diana's mouth, I succeeded in giving my Diana a thorough fucking with the strap on whilst she was standing, bent over leaning against the bedroom wall. Diana enjoyed it so much she squirted. Her orgasm may have been helped by Charles taking her 'clitoris' in his mouth. It was so exciting seeing my Charles on his knees sucking cock.

I'm so glad I fell over in the rain and Charles rescued me. He's such a lovely man and has now become an important part of our unusual family.