Joanna Goes For Training Ch. 04

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The unexpected happens on a weekend away with friends.
6.5k words
4.37
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Part 4 of the 4 part series

Updated 06/09/2023
Created 08/06/2019
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Quietoldie
Quietoldie
1,014 Followers

Coleen and Andrew get on well. He's the ideal lover, kind, considerate, friendly with no complications. Coleen finally gives in and allows Andrew to fuck him and enjoys it. Sadly after a few months Andrew has a change of job which takes him a hundred miles away from the couple's home. They try to keep it going but soon realise it's impossible.

"We need to find someone nearby darling." Joanna says. They are in bed together naked, cuddling close. Joanna is behind Coleen stroking her husband's nipples and licking his ear.

"You understand my need for a real man with a real cock don't you darling?"

"Of course I do. And I love to watch you fucking someone else, it completes our marriage, doesn't it?"

"Yes, I'm so glad you understand and love it almost as much as I do. Shall I go somewhere there's dancing and see if a man takes a fancy to me? You could sit and watch from a distance."

"No, that's too risky. You know what happened with John. There's a guy I know who might fit the bill. He's the son of Derek, the fella who became a friend through me attending Sam's group. I've kept in touch as you know. His son's about 22 and physically fit. He plays rugby semi-professionally."

"Oh, what makes you think of him? Seems a bit young don't you think?"

"I've met him a few times. He's single. I'd say he's quite mature for his age.

Handsome and easy going. He knows his dad's a sissy and takes it in his stride. I can have a word with his dad if you like and see what he thinks."

"Okay darling, but we'll take it slowly if Derek's okay with it. Do you and Derek still have a sexual thing going together?"

"Yeah, occasionally, after a few drinks in the pub."

"Does Derek put his penis in you?"

"No way. He has asked but I didn't fancy it even though I allowed Andrew to do it. Derek's a sissy. It's different with Derek. I put my penis in him though."

Joanna giggles. "So, you're the postman and he's the letterbox?"

"In a manner of speaking, 'Yes'." We both laugh out loud and roll about the bed.

"I do love you darling. We get on so well together these days, don't we?" Joanna says.

"Yes, we do. And I love you, as I'm always telling you. You will have to rely on me for your orgasms until we can find a replacement for Andrew."

Joanna manoeuvres herself onto her back, opens her legs wide and points to her pussy.

"What's this rugby player called darling?"

Coleen's already munching on her pussy but lifts his/her head to speak.

"Toby."

"Mmm. Let's hope he has a nice big cock." It isn't long before she's moaning through her first orgasm.

When Coleen asks Derek, he's sceptical at first. "He's not much of a 'lady's man'. He's only had a couple of girlfriends. Last one was over a year ago. She dumped him and he's lost confidence since then. He lives in a rented flat not far from your house but often has his tea at ours. He always was a bit shy and hasn't got many friends."

"Shall we leave it then?"

"Well, give me a bit more time to think about it and if I decide he's suitable for your Joanna, I'll sound him out. One thing in his favour, he knows all about his mum's extra marital relationship. We were up front with him from the start and he's accepted it well. Her boyfriend doesn't come to the house if he's around, so they've never met. At first, he was amused more than anything. It's helped that he's been able to look on the internet and now realises how prevalent it is these days."

A week later Derek rings when Coleen is out. Joanna asks if he's spoken to Toby.

"Yes, I've discussed it with Toby over the last week. Very embarrassing at first but he was grinning and seemed pleased to be asked. He's given it a lot of thought and is inclined to take you up on your offer."

"From what Colin tells me he doesn't sound like your average bull. But if you two sissies think he'll be okay I'm willing to meet him and perhaps take it from there. No promises of course. I'd like to check him out on neutral ground. Perhaps I could meet him in a quiet pub in another part of town away from this neighbourhood. How does that sound to you?"

"Do you know The Castle? It's on Castle Street. It probably fits the bill."

"No, never heard of it, but I'll be able to find it with Google. I'd like to meet Toby on my own the first time. I'm sure Colin will want to check him out too. But it's not really up to him, is it? Does that make sense to you?"

"It makes absolute sense. How about Tuesday early evening. 7 o'clock?"

"Okay. Will you ring me to confirm Toby's available that night."

Colin doesn't mind being left out of their first 'date'. Joanna makes most of the important decisions nowadays and he's okay with that. She makes a special effort to look sexy for Toby, plunging neckline, short skirt and dark stockings with a suspender belt. She also wears her sexiest bra and panties although she's not expecting to strip for him. Colin watches her showering, trimming her cunt hairs, putting her makeup on. She's done this in front of him before of course and it never fails to arouse him, his five-inch penis at full stretch threatening to burst out of the panties he's wearing. He goes to kiss her as she leaves but she points to her cheek.

"I don't want to smudge my lipstick, darling, you'll have to settle for a hug."

Joanna is quite nervous as she enters The Castle pub. She's missed having Andrew around to look after her needs. Colin's idea of sexual play is fine in its way, but not enough for her anymore. Will Toby be a suitable substitute for Andrew? The pub is empty apart from a young man over in a quiet corner. It must be him. She feels that special thrill of excitement and arousal and her panties moisten a little. Forgetting her nerves, she strides confidently over to him.

"Is it Toby?"

"Hello Joanna." He stands up, shakes her hand, then impulsively bends to kiss her on the cheek. He brings her a soft drink as she's driving. They sit down at the table opposite each other. She's bowled over by his good looks, handsome doesn't quite cover it. He's wearing a suit and tie as if he's going to a posh do but she likes the fact that he's made such an effort to look nice. There's an awkward silence at first and Joanna can see that Toby is blushing.

"There's no need to feel embarrassed," she tells him smiling. "I expect this must be your first time, whilst I've done this a few times before. My hubby encourages me to have relationships with other men. I don't allow him to see other women. I believe your mum and dad have a similar arrangement. I admit it would be seen as strange to a lot of people but some marriages can be happy and long lasting based on an agreement along those lines. Would you say that your parent's marriage is a happy one?"

"They seem to be very happy now. But she's only been seeing Peter for a few months. I've been told that it's fairly commonplace these days."

"Yes, so I believe. Please can you tell me a bit about yourself, interests, hobbies, employment. I'm told you play a lot of rugby. You can start with that if you like."

Toby looks a bit more relaxed. Rugby takes up a lot of his time. He's hesitant about what to tell her but Joanna asks intelligent questions and his confidence grows. She tells him things about herself and before they know it an hour has passed. Joanna finds that she likes him, he's polite and interesting, not arrogant in any way taking an interest in what she has to say. She feels she can get along with him. He's looked at her cleavage and admired her legs but discreetly, avoiding staring. Her panty crotch is wet and she wonders if he'll agree to them getting more 'acquainted' immediately.

"I've parked my car around the back of the pub. It's on a bit of waste ground. We can relax there and won't be interrupted. Are you okay to go somewhere we can cuddle in privacy?"

Toby looks a bit surprised but nods and gives her a shy smile.

The area around the back is in darkness. She presses her car keys and hears the familiar click and flash from the side lights. They move the front seats forward and climb into the back.

It reminds Joanna of her first sexual experience in a car when she was eighteen and she begins to giggle. They start with a long kiss. He touches her breasts through her clothes whilst their lips are locked together. Joanna unfastens the buttons down the front of her top allowing him access to her bra which he soon lifts from around her boobs. When they come up for air after sharing tongues Toby says,

"My last girlfriend broke up with me because she said my penis was too big for her."

Joanna starts to laugh. "I'm sorry for laughing my darling, it's just that I'm definitely not going to have any problems on that score." She kneels down on the floor of the car, unzips him and pulls his cock out. It's all she'd hoped for and more.

"Can you suck it? No-one has ever done that for me."

"Happy to oblige. I love giving head." Seconds later he squirts, giving her a mouthful of creamy spunk. His frantic moan as he ejaculates and a horrified "Oh no!" speaks of his inexperience.

"Don't worry my love. I've got a solution for that." She sits back onto the seat. "Pull my skirt up as far as it will go and pull my knickers off. Now get your head between my legs and start licking.

"Good boy. I know I shouldn't ask but you're not a virgin, are you?"

"No, of course not."

Joanna takes hold of his cock which is beginning to show some signs of life.

"It's been a while since I had a proper fucking, so I'm determined to feel that magnificent cock up my cunt tonight. Ah... You're getting hard again. I'd better make sure you're nice and stiff. I do love a stiff dick up me. Stop licking for a minute."

She's quickly back on the floor with her mouth on his cock. Pretty soon, it's even bigger than earlier.

"Fuck me Toby, there's no danger of premature ejaculation this time, you'll see."

Sure enough, in spite of the enclosed space, he's balls deep inside her, fucking her with long strokes which have found her G spot. It's now her turn to orgasm. She thought her first lover Mike was good, but Toby is better. She can't believe her luck in finding such a man. Soon she's having further flushes, one after another and Toby is showing her that he has the stamina to satisfy her completely.

Colin has met Toby before so he accepts Joanna's assessment of her new lover.

"I can see by the way your eyes are shining that you've found the right man." Colin says on her return home. "I thought you just wanted to talk to him." He grins and hugs her. "Did you put your panties back on to save me his cream pie?"

"Yes, of course, I know how much you like to eat my lover's spunk. We were delayed after he fucked me by a group of doggers so it may not be as fresh as you like it."

She pulls up her skirt for him, drops her panties to the floor stands with her legs apart. "Kneel down like a good sissy and get your tongue to work whilst I stand here. There's plenty of it."

Colin wants to watch his wife whilst she fucks her men and loves the taste of fresh come so he isn't quite as excited by the slightly stale liquid. However, it's got a distinctive taste that he's never had from her other lovers, and quite thick, nothing like the watery kind that's all he can produce. He pauses and looks up at her towering above him.

"Did you say he took you dogging?" He drops his head to continue slurping up Toby's spunk.

"No silly. We did it in my car round the back of The Castle. As we were finishing there was a knock on the car window. Four cars were arriving for a dogging session and they'd assumed we wanted the same. I wound down the window and told the guy we'd only just met. He'd already taken his cock out and reached in to stroke my tits. I allowed that as I was feeling so sexy but I could see other men approaching.

'We are not here for dogging.' I shouted as his hand moved to my cunt. The others could see what he was doing and ignored my comments. Apparently, there's some kind of protocol for this kind of thing so I could see them unzipping themselves and forming an orderly queue. Pushing the guy's hand away, I tried to clamber over to the front seat semi-naked. Toby had so far not intervened but he sprang into action, pushing the guy's arm out of the window and closing it, telling the man to "Fuck off, you cunt." It was quite a struggle trying to climb behind the wheel due to the head rests. I succeeded in lifting one off and got over. The doggers were now all round the car peering in. I just wanted to get away although I can't deny that seeing the men with their cocks out whilst I displayed my tits and cunt to them gave me quite a thrill. Once I had the lights on and the engine running, they all backed off and allowed us to leave, one or two were clapping and cheering.

I apologised to Toby but we couldn't help but laugh. Toby said that in the first few seconds of their arrival he was thinking I'd arranged it. I found a quiet road and parked up. We made ourselves look more respectable with me still without bra and panties. More kissing and stroking followed but we didn't dare fuck again. Mostly we talked, it was clear that both of us wanted to see each other for more fucking in the future." Joanna ended her rather longwinded explanation which Colin found interesting and quite erotic.

"So you got a kick out of being molested by the man who stuck his arm through the car window, did you?"

"Yes, I feel guilty about it. He was quite good looking. I'm such a slut, aren't I?"

"Yes, but you're my slut. Shall I take you dogging some time?"

"No thanks darling. Once was quite enough."

With the problem now solved Colin and Joanna get into a routine. Toby comes over to the house twice a week usually. At first, he wants Colin out of the way to give them some privacy. This is very frustrating for Colin who is relegated to sitting in the poorly heated cellar. Joanna becomes annoyed with his constant complaints about it. She gets Toby to strip him and tie his hands behind his back for a couple of weeks whilst they fuck. He's given an old blanket to wrap around himself. Joanna is obsessed with Toby in those early weeks hardly giving any thought to her husband. Colin, begins doing most of the household chores. She still loves her husband and is grateful for his help. One day she has a flash of insight after noticing him with a very sad expression on his face.

"You know I still love you, don't you darling?" She says one day. "I've been neglecting you, haven't I? I'm going to have a word with Toby. You want to watch me fucking with him, don't you? He's the man of the house now, isn't he? I'll see what he thinks."

"Thank you." Colin says.

Toby was visiting later that day. As he came through the door, she goes to him and kisses him. "Can we have a chat darling, before we go upstairs?"

Coleen was in his usual place in the cellar. He/she'll often pull on the little willy whilst he's down there.

"I've been wondering about my sissy. Winter's approaching and the last few days have been so cold. Do you think we could let sissy come and watch us in the bedroom? She's been a good girl lately and I know she'll behave herself."

"Okay, Jo, but I want her dressed as a sissy with a dress and panties on."

"Good idea, she can be our slave and we can order her around."

"Okay. What did you have in mind?"

"You know, licking my bum when I'm going down on you, holding my legs open for you, that kind of thing."

"Sounds like a plan. And if she misbehaves, I can spank her bottom. Let's do it."

Joanna shouts down to Coleen and explains what has been decided.

"Quickly now, make yourself presentable and join us upstairs, good girl."

Coleen is already dressed in her girly clothes, so it doesn't take her long to freshen her lipstick and adjust her blonde wig. She assumes her most submissive posture and thanks Toby profusely for allowing her to watch.

"Just do as you're told Coleen or you'll get a spanking you'll never forget." Toby says.

"Yes, sir." Coleen attempts to curtsy but it doesn't quite come off. Toby and Joanna look at each other and grin. From then on, she has been allowed in the bedroom whenever Toby visits. Occasionally Toby expects her to suck his penis back to life and Coleen is happy to oblige. Joanna loves to see her husband on his knees with his mouth full of cock showing his subservience to a superior man. She encourages him to swallow the jizz which he does with relish. To all intents and purposes, he is, of course a woman now, albeit a woman with a small penis. Joanna rarely lets him fuck her, she mainly turns to him for cunt licking duties when she's feeling randy and Toby is not available to fuck her.

His boss at work became aware of the cross dressing. The boss involved the staff department and he/she has been allowed to become Coleen at work. This involved moving to a different site to work as the personal assistant to one of the managers. Only a few of the staff at the new site are aware of the change of gender and he has become accepted as female there, albeit a slightly butch female.

As time went on and Joanna's 'affair' with Toby established itself, everyone relaxed with all the complicated relationships becoming free and easy. There is;

Coleen's friendship with Derek, Joanna, her bull Toby, (her husband/sissy Coleen) and

Derek, a good friend to Coleen, Mary, her bull Peter and (her husband/sissy Derek).

To fully clarify Toby is Derek and Mary's son.

Joanna has an idea. It won't be difficult to arrange a meeting with all six of them in a pub.

As soon as they had all gathered and are sitting around a table Joanna says,

"I'd like to make a suggestion. This will only work if everyone's on board with it. We all seem to like each other, don't we?" Looking around all of them are nodding, some looking puzzled and less certain.

"Okay, how about all six of us going away for a long weekend staying in a nice hotel? I know this is controversial, so I want all of you to think it over for the next two weeks. If anyone is not sure about it, we can forget the whole thing. Toby and Peter will each have a double room to themselves. We need to share email addresses. I will take care of the booking, but I expect the cost to be shared equally. Write to me with any questions you may have."

Fourteen days later all six are in agreement that it is a good idea. The booking is made in Blackpool, a seaside resort in the north west of England. The journey up the M6 on the Friday is uneventful apart from congestion for part of the way. After they have booked in and unpacked, they meet downstairs in the bar. Coleen is dressed enfemme whereas Derek has favoured a fairly androgenous look although he is not wearing anything to attract attention to himself.

"I've been doing a bit of research and there's a place here called "Funny Girls." Joanna says, taking charge. "The staff are all crossdressers, the women dressed as men, the men dressed as women. Apparently, it's a good show. The compere sometimes picks on someone in the audience and takes the piss but it's all done in fun. You'll enjoy it provided you don't mind all the swear words."

Everyone is up for it. Coleen rings the place to find their first night fully booked so they book for the Saturday. Apparently, the town is popular with stag and hen parties. Looking around in the bar there are a couple of groups in fancy dress, one a stag, the other a hen.

They take a walk along the prom in the area around the hotel but no one is interested in drinking in the bars. The north pier is nearby and they walk to the end. Coleen and Derek wander off together saying they'll see the others later in the hotel bar. Joanna hangs onto Toby's arm whilst Mary does the same with Peter. When it starts raining the four of them return to the hotel. In the bar Joanna finds herself sat next to Peter. She first met him at Sam's and remembers noticing that he was well endowed as the men performed "You can keep your hat on." As they are chatting, she can't stop thinking about his cock and her eyes are drawn to his crotch area although she's trying hard to avoid making it obvious.

Quietoldie
Quietoldie
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