Crossdresser Frank Is Cuckolded

Rob had always considered himself as straight but recently had been attracted to watching videos of men crossdressing and masturbating.

One in particular caught his eye, that of a middle aged man wearing sexy ladies underwear and heavy, slutty make-up. As the man pleasured his rock hard cock Rob would do the same and held back so he would cum at the same time as the man.

Later he found out that the man lived only about 10 miles from him and Rob messaged him and asked if he could visit him and watch him in real life.

Surprisingly the man replied that he'd like that. He said his name was Frank and Rob arranged to visit him one Saturday afternoon.

Rob nervously walked up to the front door and rang the bell. He wondered how Frank would greet him. He was surprised when an attractive middle aged large lady opened the door and said, 'hi, you must be Rob, I'm Sarah, Frank's wife, come in.'

He followed her into a sitting room. He was mesmerised by her lipstick. It was such a striking colour that he couldn't take his eyes off it.

She said, 'Frank is just getting ready, he'll be a few minutes, he's very particular when it comes to his make up.'

She asked, 'are you a regular when it comes to visiting crossdressers?'

'No, this is my first time. I've always liked the feel of ladies underwear against my skin. I often wear my wife's soiled underwear when I masturbate.'

'Are you wearing any now?' she asked.

'No,' he replied.

'Would you like some,' she asked.

'Yes, that would be nice,' he replied.

Sarah stood up and took her panties off and handed them to Rob and said, 'you might as well wear these.'

As she handed to them he looked closely at them and she said, 'you can keep them and every time you masturbate. It will remind you of today.'

He looked at them closely. She could see what he was thinking and said, 'yes, it's OK, I don't mind you smelling them.'

Rob held them to his nose and inhaled the wonderful aroma of the sexy lady's intimate places.

He said, 'Frank seems a long time.'

'He takes a while putting his make up on,' she replied.

'By the way, I like your lipstick. You have very kissable lips,' Rob said.

Sarah smiled and said, 'Frank calls them my cock sucking lips.'

Rob asks, 'do you mind men visiting Frank, knowing they've been turned on watching him pleasuring himself?'

'Not at all. What you and they don't know is that it's me filming him and he's watching me play with myself.'

'Wow, that's really horny. Do you often watch each other masturbate,' Rob asked.

'Yes, of course we both love fucking, we both love wanking and watching each other wank,' she replied.

At that moment Frank walked in. He had a short blonde wig on, dark eye shadow and the same slutty red lipstick as his wife. He wore a red basque with suspender straps holding up fishnet stockings and red high heel shoes with ankle straps. He had a pair of open crotch panties on, his erect cock poked out through them.

Rob wondered how things were going to progress.

Frank said, 'Rob you said you wanted to watch me wank. The video you looked at actually had me looking at Sarah while she wanked. Do you want to watch both of us?'

Sarah said, 'as Rob has told me he likes to wear ladies underwear why don't I help Rob dress and I can have two sissies wanking while they watch me.'

Rob undressed, his erection was showing through Sarah's panties that he was wearing.

Frank said, 'I recognised those panties. I've worn them a few times myself.

Sarah strapped a suspender belt around him and as Rob sat down she pulled a pair of fishnet stockings up his legs making sure she brushed against his cock. Then a pair of 5 inch high shoes. As he stood up his erect cock stood out in front of him.

Sarah said, 'just some make up then it's my turn to dress.'

She coated Rob's lips in the slutty red lipstick that she and Frank were wearing. Then topped hers up as well.

As she left the room to dress herself Rob said to Frank, 'I really want to kiss those sexy lips of hers. Do you mind?'

'Not at all, help yourself. I also want you to lick her cunt so I can watch her cum while you're tonguing her,' he replied.

They waited a few minutes and Sarah came in. She looked stunning, wearing a black latex basque with cut outs where her tits are. Her erect nipples looked very suckable. Seamed stockings, no panties and high heel shoes completed her slutty appearance.

Then she put even more lipstick on.

Rob looked at Frank and nodded to him.

Rob said, 'Sarah, may I kiss you?'

She didn't reply but just stood in front of him. They both wore the same red lipstick and their lips locked together. Their mouths opened and tongued each other.

Sarah reached down and felt Rob's erect cock. Frank was already wanking while watching them. She took his hand and put it between her legs and said, 'this needs a good fucking and licking.'

She looked across at Frank who nodded to her.

She sat on the sofa with her legs apart and Rob knelt between them. He just loved the look of her very wet cunt.

As he lowered his face towards her he could smell her sexual arousal. She needed it now and pulled Rob's face hard down against her very wet cunt. Frank was standing close to his wife and wanking while staring at her.

Frank said, 'lick my wife's cunt, suck her clit, make her cum.'

Frank was inches away from his wife's face and frantically wanking his cock. Rob was loving the taste of Sarah's juices as he licked up and down her slit. Her juices were flowing freely and soaking Rob's lipstick coated lips.

Who would cum first, Frank or Sarah?

Suddenly Frank was there. He told his wife, 'open your mouth.'

She did as she was told as he emptied the contents of his balls deep into her mouth. She had her mouth wide open with the pleasure that Rob was giving her with his tongue. Her husband's cum was trickling out of her mouth and over her beautiful red lips.

Rob started concentrating on her clit and as his tongue and lips massaged it she had the most enormous orgasm ever.

The remains of her husband's cum was now gushing out of her mouth, over her red lips, down her chin and onto her chest.

She gasped for breath and quickly recovered and realised that Rob hadn't cum yet.

Frank was getting himself hard again and said to his wife, 'let Rob fuck you.'

Sarah was more than happy for this to happen. As much as she enjoyed oral cumming she also needed a fucking from a hard cock.

Rob slipped all the way in as she was so wet. He knew she wanted to cum again so had to hold his climax back, with difficulty.

Frank was hard again and wanking in front of her face again. After a few minutes of intense fucking Sarah cum again just before Rob emptied inside her.

Frank was now licking his cum that had run out of his wife's mouth and onto her chest and as he was about to cum again he spurted all over his wife's tits.

From that date on Frank and Sarah's sex life changed. They still watched each other masturbate while he crossdressed but every 8 or 10 days Sarah would say, 'it's cuckold time,' and Frank would ask Rob to come round and take care of Sarah's needs while he watched and wanked.