Old Lady Fucks Her Cross- Dressing Friend free porn video

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Hazel was fed up using her fingers and dildos and fed up of being one of the invisible elderly generation. 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 36D bust and welcome either gender and any age.

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 liked feeling feminine they critically also liked fucking women – which was the part she was looking forward to.

Howard was the one guy who 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 of what she could do for him and he for her.

‘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 that 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 my 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 slowing wanking him, he continued his story.

To cut his rambling story to the core, it was when he was 14 and his mother used to send him to their neighbour and 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 she pulled his cock out and started wanking it 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 that he shot loads of extremely thick creamy spunk.
For Hazel to get the most satisfaction – and fucking – from Howard, she thought it best to recreate his first experiences but bypassing the first bit and focusing 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 liked only dressing in women’s ware only – stockings, garter belt and skimpy knickers. Sometimes he put on a 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 more randy, 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 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 flabby thighs as far apart as possible.
‘Now, Howard, will you gently finger fuck my cunt’. As he leaned over and placed his hand over her lovely hairy protruding 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 put a finger on his shitter 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 you 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 shortish 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, Hazel said: ‘Howard baby, will you fuck me slowly until I cum but I don’t want you to shoot your love juice as I have special surprise for you 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 Howard 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 the strap on 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.

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Cherri was a sixteen year-old school girl. The loveliest and hottest looking young girl in school. Since she reached puberty folks have been saying that she was a very beautiful girl. Recently they have described her as being exceptionally gorgeous and voluptuously sexy. She had a baby face with sparkling eyes and rosy cheeks and luscious lips. Her blond hair cascaded in lovely curls down to her shoulders. Her face alone, together with its captivating smile, could arouse even an impotent man,...

3 years ago
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Crossroads A Young Hero

I walked through the headstones towards Dad's car. It was my car now after that accident. I was walking away from the double funeral for Mark and Carol Arrowstone. It was less than a week ago that I had come home to the cops sitting in my driveway to tell me that Mom and Dad had been in a car accident. The drunk driver that hit them was dead too. Standing next to the car was Mike Larter, Dad's lawyer. He was handling the reading of the will and the distribution of my parent's assets. I knew...

2 years ago
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Katherine becomes a Lady

My father stood in the doorway to my room and through the bitter moonlight I could see he wasn't happy. His scowl had a way of sucking the air out of a room. We were all terrified of that scowl. I found myself wanting to do anything to make him not stand in my doorway with that look. My sisters rooms would be fine but mine, no way. “Daddy?” I said . He stepped into my room but the look didn't change. I felt tears sting my eyes. I was terrified! What had I done? What was he about to do to me? I...

Incest
1 year ago
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Cross Dressing play turned horribly wrong fantas

It was just another warm Sunny weekday morning like any other in summer. My wife kissed me goodbye as she left for work, I took my usual pervy glance at her as she wiggled her hot behind out the door, I was setting up in my home office, ready for another day of working from home. I listened to the car roll out the driveway then the gate closed, I started working through the usual emails and meeting requests.. I got bored of work after a couple of hours I decided to go into our bedroom and rifle...

1 year ago
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Far Future Fembot DarleneChapter 45 Lady Heather Redux

Thoughts This had to be the greatest shock of my life. Greatest because I was hit by two massive bombshells at once. The first was Lady Heather - not Anna being Lady Heather, but the real one - standing deactivated inside the small, protected room. The second was that Anna had managed to keep this secret from me all this time. I looked at Anna, my questioning expression too obvious to need further elucidation. "Information referring to this exists in a special spot I was able to create...

3 years ago
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91 AVIS AND HER LADYFRIENDS

91 AVIS AND HER LADYFRIENDS My friend Carol called me up one morning and asked if I would like to meet for some shopping and lunch. Since Jon and I would have the day to ourselves, I agreed and we met at the local mall. Carol approached me and unexpectedly kissed me there in the entrance way to the mall. "Good morning" she said as I looked back in mild shock. "Did I shock you?" she asked. I said I was a bit surprised, but then let it go and off we went shopping. Around noon we stopped at...

3 years ago
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Olde Tale of Herbs Healing

(Author’s Note: This tale is a ‘period’ piece. Liberty has been taken with the use of Olde English in the writing to match the tone of the times.) Nearing the top of the turret stairs, the challenge rang out ‘Who goest there?’ ‘Tis I, Lord Robert, Giles.’ was mine response. ‘M’Lord, thou art the only stir upon this cold clear night.’ ‘Is that not good after many years od struggle, Giles?’ ‘Aye, M’Lord. All thy subjects give ye thanks to now live in peace and comfort. Tis our good fortune...

3 years ago
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It Starts Again A Cross Dressing Fantasy

It had been a particularly hard week at work and was so happy to pull into the garage and put the door down. I sat a moment looking at the empty space in our double garage wondering why Beth was not home, and the remembered that she said she was working until 8:00 PM tonight.I walked into the house, kicked my boots off, dropped my lunch box by the sink, and stripped my shirt off as I headed to the bathroom to get a much needed shower. Our laundry closet door was open so I deposited my work...

2 years ago
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Preachers Daughter Chapter 18 Preacher and Preach

For those following the stories, we are at the point Jaimine, the preachers daughter is six months along carrying my baby. She lived with my wife and I, my hot wife Charlotte clueless about Jaimie.Jaimie 24 birthday was yesterday! So, what we did was I had my wife set up a nice surprise party for her at our house where she lives when she got home from her college classes before Christmas break. My wife had no idea, when she left for work and our k**s left for school, Jaimie, who lives with...

2 years ago
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Preachers Daughter Chapter 18 Preacher and Preach

For those following the stories, we are at the point Jaimine, the preachers daughter is six months along carrying my baby. She lived with my wife and I, my hot wife Charlotte clueless about Jaimie.Jaimie 24 birthday was yesterday! So, what we did was I had my wife set up a nice surprise party for her at our house where she lives when she got home from her college classes before Christmas break. My wife had no idea, when she left for work and our k**s left for school, Jaimie, who lives with...

3 years ago
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Cross Dressing to go to Girls School

As a boy I was slim and in some ways feminine looking. For example it used to annoy me when I went into a shop with the hood of my coat up because of the weather to be addressed as “hen” rather than “son” – these being terms used in the Glasgow area back then. I went to a co-educational school and had a great time with the girls I met there, all the way from my first day in “primary one” to the sixth form. I did have a fling with one of the PE teachers there brought on by too much to drink...

2 years ago
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Therapy for Cheri

Therapy, Part 1It was my medical doctor who suggested that I should speak to a counsellor, or ther****t about my sexual fantasies, and how they had started to overwhelm my life.  At first, I was not particularly interested in talking to anyone about this, but obviously my doctor felt that a counsellor could help me, and that not seeing one could eventually harm me.I booked an appointment for two weeks ahead, thinking that this would give me some time to get my shit together, and I could call...

2 years ago
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Preachers Wife Chapter 3 from Preadhers Daughter

Pam, the MILF preachers wife did as I ordered her. She did give me those panties from her cunt at church as ordered and when I called the Preacher's house the week after I first fucked her, I asked if her husband was home. Yes she said, very well, tell him you are going shopping at the mall and Christian book store. Go buy things at the book store first, then meet me at the pet store in the mall. You are to go into the bathroom at the Christian bookstore and remove your panties, and have them...

4 years ago
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The landlady Steve and her Friend

Steve sat in his living room, trying to relax from a long day. He had been traveling since early the day before, only stopping at a cheap motel to grab a few hours of sleep. The trip had been a success and would likely pay off for him greatly, so he was in a good mood, but just a little road weary. Having arrived home and done little more than walk into his house, drop his bags and plop on the couch, and pour an accidentally large glass of bourbon, he wondered if a good hot shower would help...

4 years ago
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My first black cock as a cross dressing schoolgirl

It’s 1995, and I’m in year 9 at school. I’m been cross dressing for longer than I care to remember. I’m fascinated by tights, and I’m fortunate to be at school in the era of the Spice Girls and Girl Power. Skirts are as short as possible, and everyone is wearing platform shoes. I’m in my element. I’ve recently discovered my best mate also cross dresses, but he’s lucky in having a slightly younger sister who has a very nice wardrobe to raid. I’ve also discovered he’s a very heavy cummer, and...

2 years ago
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Wanted A Horny Crossdressing male

Information: This story is set out as an ad in a porno magazine but it is entirely a work of Fiction I invented. It should be taken of somewhat as a joke. Wanted: A Horny Cross-Dressing Male Hi I'm Foxy Roxy, you may have seen me in action in one of the many porn flicks I've been in, but if you haven't, here goes. I am a thirty-six year old married woman with big tits and blonde hair. I like to wear a leopard print crop top and matching pants. I'm always horny and up for...

4 years ago
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Cross Dressing Pegging and the Promise of a Three

After my last session with Ann, the gorgeous older woman (we’d call her a MILF nowadays) who’d discovered my love for cross-dressing, things were quiet for a couple of weeks. She’d only ask me to visit her when she knew her husband and son would not interrupt which so far meant when they had gone off to watch their football team playing away. It seems that they had a run of home games.Mind you, keen as I was to play with Ann again I did also enjoy replaying our sessions whilst lying on my bed,...

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