Dinner with Annie was good. It was relaxed. First dates can be nervous affairs. Even though, in this instance, sex at the end of the evening was expected, there was no certainty that it would happen. The wrong word, the giving of the wrong impression could kill the evening off in a heartbeat but the sex hurdle had been cleared. Well and truly by all accounts, because Annie had already thanked him for such a wonderful time.

“It was a wonderful... “ She had started to say.

“Fuck?”

She smiled coyly.

“It’s okay you can say it,” Larry told her. “Girls are allowed to use the F word as well.”

She smiled shyly at him.

Larry leant over and kissed her. “I enjoyed your cunt very much,” he said very quietly. “I look forward to getting to know it a lot better.”

It brought redness to her cheeks but she still managed to whisper to him, “I... I loved your cock too and I look forward to it getting to know my cunt a lot better.”

Larry smiled as he turned his attention to his fillet steak with thoughts about renewing his assault on Annie’s cunt later.

They chatted over their meal and Barolo red wine. Annie revealed that she was about to begin her final year of her psychology degree. “Got my dissertation to do this year,” she told him.

“What’s your subject?”

“Fuck knows,” she shrugged.

“I can think of one.”

“Oh?”

“Cuckolding.”

“Cuckolding?”

Larry explained what it was. “The Psychology of Cuckolding,” Larry told her. “Has a ring to it.”

Annie looked seriously at him.

“Excuse the pun.”

“Pun?”

Larry pointed to the wedding ring finger of his left hand.

Annie laughed. “You know, I might give that some serious thought.”

“I could introduce you to couples who are into the lifestyle,” he told her. “I know a few Alpha males quite well too. They would give you their input.”

“Alpha males?”

Larry explained.

Annie laughed. “I can see I have a lot to learn,” she commented. “I take it that you consider yourself an Alpha male.”

Larry shrugged. “Far be it for me to compare myself to other men and blow my own trumpet.”

Annie smiled. “You are good,” she said quietly. “And you’re quite big.”

“Only quite!”

She laughed. “Very big,” she corrected as she rested her hand on his thigh.

“Actually I consider myself a rut-breaker.”

She thought for a few moments. “Yes, I suppose lots of couples get into ruts with their relationship over time.”

“Yes.”

Her hand inched closer. “And you’re always around to give them a hand!”

Larry smiled as he leant closer. “I’m around to give them a lot more than a hand.”

“I’ve always considered marriage to be a long way down my to-do list,” she told him. “Until now.”

“Keep it that way for now,” he told her. “Have your fun and get some life experience first.”

Back at the hotel, they fucked long into the night. Next day was Annie’s day off and Larry had nothing urgent pressing either so she put a ‘Do not disturb’ notice on the door handle to ensure privacy. A fuck in the shower next morning made him too late to take breakfast at the hotel so he and Annie met up outside and went to a cafe for breakfast. An hour later, they went their separate ways with promises to keep in contact.

A couple of days later Helen rang him. They were just five days away from their date. She was quite excited but Ian was very unsure about the whole thing now. His main concern was Helen having too much solo time with Larry.

“He really would prefer it if we did it here,” Helen told him.

“What do you want?”

“To be honest I would prefer to be at the hotel.”

“Well, you’re the boss.”

Helen laughed. “I want you to be the boss,” she responded. “But I see where you’re coming from.”

Larry had an idea and rang off. Seconds later he was speaking to Annie. She was at home in her bedroom. “What are you doing?” he asked her.

“Lying on top of my bed watching television,” she told him. “I’ve just had a long soak in the bath.”

“Mmmmm,” Larry sighed. “Wish I was there right now.”

Annie laughed. “I wish you were too, I could have done with a helping hand a little while ago.”

“Oh?”

“Just given myself a shave down there,” she said softly. “I would have preferred you to have done it. Men do it so much better.”

“Do they?” he asked with raised voice. “And have many men shaved you?”

Annie laughed. “One or two,” she responded. “One or two.”

Larry laughed back. “So few that you can’t remember, hey?”

“Four actually.”

Larry felt a twinge of jealousy.

“Would you like me to send you a picture of my freshly shaved... cunt?”

“Fuck, yeah.”

Annie disconnected the call and a few minutes later a couple of photos reached his mobile. Annie was sat back against the headboard with knees raised and wide apart displaying herself.

“You’re shameless, do you know that?” he told her when she rang back.

“Then you’ll delete them will you?” she laughed.

“No, I’m keeping them.”

“I think I missed a bit.”

“Missed a bit?”

“Yes, just inside my right labia,” she explained. “It feels a bit bristly.”

Larry sighed.

“I expect you would notice it too if you were inside me right now; fucking me hard like you do so well.”

He sighed again.

“Bet you have a stiffy don’t you?”

“You... you are so shameless for one so young.”

“I am twenty-one, you know.”

“Yes... I suppose twenty-one-year-olds today are much more open about sex than they were in my day?”

“How old you?”

“Thirty-six.”

“That’s only fifteen years difference.”

“And?”

“I like older men,” she said softly. “So much more mature than boys my age. Experienced too, I like that.”

Larry was silent.

“Grateful as well for a fuck,” she continued. “They appreciate someone much younger than them; prefer a night in having sex to being out drinking with their mates.”

“You pretty much have it sussed, don’t you?”

“Maybe,” she mused. “Anyway, why did you call?”

“I wanted to ask you about adjoining rooms in your hotel.”

“Why?”

Larry explained.

“Would you like me to see if we have any available this weekend?”

“Please.”

“And what do I get for it?”

“You get a damn good fucking.”

“But you’ll be too exhausted.”

“Will I?” Larry responded. “”I’ve done a few threesomes in my time.”

“Mmmm, I bet you have. I’ve never done a threesome.”

“Well it can be arranged,” he told her. “I mean a girl, girl, and a guy.”

“So do I.”

“You really are shameless,” Larry laughed.

“I know,” she laughed back.

“Why?”

“I’m going to have some me time with my vibrator.”

“Fuck.”

“I know,” she whispered. “I’m shameless.”

Larry rang Helen back, his mind though was elsewhere, Annie was getting under his skin and it was a feeling that he had never known before. Sure, he had feelings for the women he had slept with; he had developed many friendships and bonds but Annie was getting to him. He couldn’t quite put his finger on it but he felt different around her and he was missing her. As much as he was looking forward to meeting up with Helen he wasn’t desperate to be with her. He could wait five days, even longer, for her, but Annie? No, he wanted her now.

He didn’t stay too long on the phone with her, he was tired and needed an early night but he was also horny. He was thinking about Annie with her vibrator and wondered if she would be as shameless as Karen was. She had an assortment of sex toys; her favourite was a pink vibrator. It had a slim shaft but it was quite long and she would insert it deeply. He would sit at the foot bed and watch her slowly work it to her satisfaction.

Larry learned there was an art to it. Start off by slowly teasing yourself with it; running it slowly over the clitoris and between the labia. Letting it rest there first, taking you to the edge, before beginning its insertion. He watched her have many orgasms using it while he was with her. He also helped out sometimes. Karen’s arm would get tired and he would take over. Sometimes he would tease her clitty with his tongue while using her toy deep inside her. Karen would end up screaming as her orgasms unfolded.

He also introduced her to anal sex using the vibrator. Karen took a lot of coaxing at first; she was shy and had natural reservations but one night he got her quite tipsy with Bollinger and managed to get her naked from the waist down and in a kneeling position on his bed. With bottom raised he slowly worked in some lubrication and then gently eased the toy inside her. It took some time to get her to relax her anal muscles but when she finally allowed it to get deep inside her she quickly realised what a joyful experience it was. Three or four sessions later he managed to persuade her to try his cock for a change and after a few attempts, he managed to go the whole way with her. Karen became hooked on anal.

As he climbed into his bed with thoughts about Annie, his mobile phone suddenly indicated an alert; Annie had sent him some attachments. ‘Fucking hell,’ he muttered to himself. They were three photos taken, he presumed, from an angle of head or shoulder height as she sat up in bed pointing down her naked body. The first one showed her holding a blue jelly vibrator against her mound. The second one showed her inserting in inside her and the third one showed the vibrator held in the air glistening with her juices. He guessed that the first two showed ‘before’ play and the third one ‘after’ play. His hand instinctively reached under the duvet to hold his immediate erection.

Holding his mobile in one hand and his erection in the other he began to stroke himself. He wished he was there with her now as he remembered Karen and the times that he would take her vibrator from her hand afterwards and after putting it to his own lips to taste; he would put it to hers. Women were not adverse to tasting their own juices.

He sighed loudly as his hand movements increased. His imagination was beginning to run riot now. He remembered how he used to tease and toy with Karen making her cum time and time again with the vibrator and then fuck her quickly and hard. Many times he would fuck her doggy style taking the opportunity to pull tightly on her long auburn hair while sometimes interspersing his onslaught with hard spanks of her bottom. He could feel himself getting closer to cumming and he pushed back the duvet in readiness. Suddenly his mobile rang.

Larry cursed as he answered. It was Annie.

“Did you get my photos?”

“Yes,” he sighed.

“Anything wrong?”

He sighed again and then explained. Annie giggled. “I like watching a man masturbate,” she told him. “I wish I was there now.”

“And what would you do if you were here now?”

“I’d talk very dirty to you to help you along.”

Larry laughed. “Just talk. No helping hand?”

“Just talk,” she responded quietly. “I can be quite filthy.”

“I bet you can.”

“Are you holding your cock now?”

He wasn’t but he quickly took hold of himself. “I am now.”

“How do you hold yours?”

“Thumb and four fingers.”

“Not in a fist?”

“No.”

“Do it slowly,” she said softly “Move your hand up and down slowly as you grip tightly.”

Larry sighed.

“Now close your eyes,” she whispered. “Imagine me sat back opposite you with my knees raised and legs apart.”

He groaned.

“Can you see me?” she asked. “Can you see my cunt all wet and opened out for you?”

A louder groan escaped his lips.

“You can see it can’t you,” she responded. “Ready, wet and beckoning you; calling out for your big thick cock. You can see it can’t you Larry?”

“Fuck yes!”

“Cum for me now, Larry; cum for me.”

Larry cried out.

“I bet your cum could reach me couldn’t it Larry?”

“F-U-C-K.”

It took a few minutes for him to recover. Annie was still connected, patiently waiting for him. “You’re something else, Annie,” he told her. “Something, fucking, else.”

She giggled.

“Just wait till I get my hands on you again.”

She giggled again. “You’re not in the area on Thursday by any chance are you?”

“No, not until Friday and then I’m seeing Helen. Why?”

It’s a pity,” she told him. “Mum and Dad are going away for a couple of days. I will have the place to myself.”

Larry said nothing.

“I could offer you five-star accommodation with personal services thrown in.”

“Personal services?”

“Yes, personal services,” Annie responded. “I like to dress up for the older, more discerning gentleman.”

His cock was stirring again. “Dress up?” he croaked.

“Mmmm,” she murmured. “Discerning men appreciate costume.”

“Costume?”

“Basque, stockings, heels.”

“Fucking hell!”

“Maybe a riding crop.”

“Riding crop?”

“Older gentlemen tend to be quite naughty,” she told him. “Very naughty sometimes; that’s when some discipline is a required.”

Larry was fully erect now. “Discipline?”

“Discipline, Larry,” she repeated. ”They need to be taken firmly in hand.”

Annie had sent him tumbling again; tumbling down a path he had never considered before. He had friends who had. Discerning older men, as she put it, who enjoyed the services of a dominant female disciplinarian.

“Are you still there?”

“Yes.”

“And?”

“It... it’s not really my scene.”

“Just because you’ve never tried it doesn’t mean to say you wouldn’t like it.”

He was silent again.

“But if you prefer just to come and stay with me without... without the personal services then it's fine,” she told him. “I still want you.”

“Let me have a think about it,” he told her. “I... I might be able to reschedule my work.”

“That would be nice Larry,” she responded. “I need that cock of yours and... the riding crop is always available if required.”