Old Lady Plays with Crossdresser

Hazel was fed up using her fingers and dildos and fed up with being one of the invisible elderly. She wanted more -- a lot more -- sex, so she decided to expand her sexual horizons. To ensure that she put an advertisement on the web. "Larger mature lady, single, (70), open-minded seeks new experiences, fun, and frolics. I am 5" 4", dress size 18 with a 36D bust, either gender and any age is welcome.

She was amazed that it attracted a few older cross-dressing men, which surprised her greatly but being intrigued, agreed to meet some of them. She knew that while they liked dressing in women's clothes -- especially lingerie - and feeling feminine but critically also liked fucking women -- which was the part she was looking forward to.

Howard was the one guy whom she was attracted to as he seemed very polite and charming on the phone so Hazel invited him round to hers for coffee. Her initial assumption of him proved spot on.

He was 40, slim and well-dressed but quite shy and it took a lot of sympathetic listening and gentle rubbing of what she considered a nice-sized cock, for him to tell his story.

"Hazel, for the last 25 years I found that I could only really enjoy sex dressed in women's lingerie and dresses and skirts. Nearly for all that time, I had to use prostitutes because my skinny bitch of a wife thought I was perverted and who in fact didn't like sex anyway. Your advertisement suggested to me that you might be more open to my fetish. Would I be right in that?"

"You certainly are Howard. And I am looking forward to it. In fact, thinking about you fucking me dressed up is making me quite wet. Tell you what, while you are telling me why don't you caress my lovely wet hairy cunt?" With that Hazel got up and pulled down her knickers and then sat beside him, her fat cellulite dimpled thighs wide apart to give him good access.

With Howard's hand nestled in her hairy twat gently massaging it and her hand in his trousers slowly wanking him, he continued his story.

To cut his rambling story to the core, it was when he was 19 and his mother used to send him to their neighbour a middle-aged shapely lady to do odd jobs. Her name coincidentally was also Hazel. He was very attracted to her nylon-encased legs and she, pleased by the attention, used to encourage him to give her foot rubs. One day, she caught him in the bathroom, wearing her knickers and furiously wanking. He of course was embarrassed but she, he said, looked delighted and took over his dick to ensure he came.

From there is a short route to him visiting her and dressing in her lingerie and sometimes a dress which she used to play with him in and then fucking her. He began to enjoy it so much that eventually, he could barely get a hard-on without wearing sheer lacy knickers.

Hazel was so worked up that she started wanking his cock like mad and told him to finger fuck her clit. She was very impressed with his very thick member and when they came almost together, she loved watching the extremely thick creamy spunk he shot out.

For Hazel to get the most satisfaction -- and fucking -- from Howard, she thought it best to recreate his first experiences but bypass the first bit and focus on the foreplay and fucking bit.

"Howard, I was thinking that as I am much older than you, it would be more playful if you called me granny when you come around next. Don't forget to bring your things with you."

Howard, it should be remembered, only liked dressing in women's underwear -- stockings, garter belt, and skimpy knickers. Sometimes he put on various dresses and skirts. He was not gay. He loved fucking women. But he loved fucking them best in women's lingerie. He was so excited about meeting Hazel, the first old lady he had come across. And when she told him to call her granny all sorts of perverted ideas ran through his brain.

Hazel was expecting him that afternoon and had decided to make dressing up part of the fun for him and her. And to make him even randier, she would play the granny role but a granny who had a downright filthy sex habit. To prepare him for the first, she had made sure that her bladder was nice and full and that her thick strap-on dildo cock was in the bedside cabinet.

He was slightly disappointed to see Hazel dressed in a very dowdy dress when he arrived but she welcomed him with a very passionate kiss saying "How nice that you made time to meet your old granny, my cunt can't wait to feel that lovely cock wrapped in frilly knickers. But before we go up and dress would you help your randy granny in the bathroom?"

Howard nodded like a dumb idiot. Taking his hand, she led him into the toilet saying, "Howard my lovely young man, Granny has a secret". Taking off her dress and blouse she put her arms around him and tongue kissing him she ground her fat hairy cunt into his now hard groin. "As I got older instead of my pee stream reducing in strength it actually increased and with it my desire to finger my cunt. Now, before we go to bed, will you help me have a lovely piss and while I am doing it, I will give you a blow job you won't forget"

Taking down his trousers, she took his cock encased in sheer nylon pants and led him over to the toilet. She sat down on the pan as far back as possible and spread her fat cellulite and flabby thighs.

"Now, Howard, gently finger fuck my cunt". As he leaned over and placed his hand over her lovely hairy fat fanny, she put his cock in her mouth and was caressing his balls. Slowly thrusting his hips Granny took in more as he started finger fucking her and she started to gush a massive piss stream over his hand. With Howard now frigging her clit like mad she pushed a finger in his shit hole and gently pressed it home. Doing that made him extremely horny and Hazel could tell he was about to cum which made her suck him harder as she wanted all his cum in her mouth. She was on the verge of orgasm and as she went over the top and felt lots of thick creamy cum in her mouth. With it dribbling down her chin, she got up and said, "I want to share this with you, my lovely boy." He didn't need any prompting as he leaned in and tongue kissed her mouth full of his cum.

A couple of hours later after they had finished a light tea, Hazel suggested they get dressed upstairs and taking his hand, led him into her bedroom. She could see that he was shy so encouraged him to show her his flimsies. By the time he was dressed in a garter belt, with sheer nylons and his thick cock crushed into see-through knickers she was getting excited and encouraged him to wear one of her short skirts and blouses.

Hazel slipped into a sheer see-through short nightie proudly showing off her big floppy titties over her tubby belly leading to her protruding hairy fanny.

Lying down with her legs wide open, she said: "Howard honey, fuck me slowly until I cum but don't shoot your love juice as I have a special surprise that will make you shoot more spunk than ever before".

Howard took off his knickers and probed her hairy wet hole, and slowly began to fuck her till she screamed herself shitless in orgasm.

After taking a short rest she got up and told him to lie face down and wait for his surprise. Hazel soon placed the strap-on cock over her cunt and after lubricating it said "pull up your knees." With his still raging hard-on, he obeyed and then felt her finger probe his arse. Once he was getting used to it, she slowly and gently began to fuck him from behind. Then she shoved her strap-on right in. His cock jumped with each thrust as it rubbed against his prostate. "Oh granny, keep going". Once she knew for certain he was comfortable she picked up the pace and Howard began to moan uncontrollably because the pleasure was almost unbearable.

Granny "Stroke my cock while you fuck me, make me fucking cum". She reached around in front of him and wanked his cock, matching her own thrusts. He shot his wad within a minute.

Lying back down she asked Howard to fuck her again. He pulled her close and kissed her deeply before focusing his attention on her supple flabby breasts, softly sucking on her aching nipples as he began to fuck her