My masturbation fantasies were often about being caught looking up skirts and then being pantied for getting caught. In these fantasies I’m a young boy and the woman catching me is always an older, sexual loving woman.
The woman was usually my mother, one of her friends or my friend’s mothers. I’ve developed many variations on the theme but the one I always return to is with the women next door.
I’m in her house sitting on the floor watching TV. She’s sitting across from me and I have a perfect view up her skirt. She’s adjusting her self in the chair and each time she does her knees part revealing more and more of her panties, stockings, slips and garter tabs.
The white “v” of her nylon panties is holding my eyes when I hear her say “You’re a very naughty boy and so curious too” I can feel myself turn red.
“Come over here. Take a much, much closer look”
She can see my excitement when I stand and walk over to her. “I can see that you really love seeing my panties. Would you like to try on a pair too? I think you’ll look just adorable in them.” Blushing red, I shake my head yes. She takes my hand and leads me to her bedroom.

This is a wonderful and fullfilling fantasies and I masturbated to its many variations.  Crossdresser Older Women Masturbation Fantasy

Here’s a picture from my photo shot with Sadie a young women that loves vintage lingerie and panties.  She made a lovely movie showing off her lingerie and panties with lotrs of amazing cloe up upskirts.

Finally!!!  a sweet romantic movie of mommy caressing and loving her little sissy girl.  The love and caring between mother and sissy daughter is a wonder to see.

You can search the net but you’ll never ever find another movie like this one.

Imagine 52 year old mommy bringing her little sissy girl daughter to her bed and fondle and caressing in very romantic and sensual ways.

Click Here to See This Clip

DEAR ABBY: Please tell me if I’m going crazy. My husband of 30 years recently admitted that he enjoys wearing my undergarments! At first I was shocked, but now I am over it. We went shopping together and bought him several pairs of panties. He was in seventh heaven.

Our sex life has never been better, and we really are enjoying each other — but still I wonder. — Mixed-Up in Florida

DEAR MIXED-UP: You are not the first wife who has helped her husband cross-dress. He is a transvestite — someone who enjoys wearing clothing that is traditionally worn by the opposite sex. Because your sex life has "never been better" and you are "really enjoying each other," my advice is to stop "wondering" and appreciate that after 30 years of marriage, your husband finally trusted you enough to show you who he really is.

Sheri Panties Matt

Renee

Matt was standing hard and throbbing, as Sheri slowly pulled the pink lacy panties up his stocking covered legs and on to his hips. He was making a beautiful, taut nylon tent in her panties.

That’s the end of scene one. That’s right. That’s from a movie playing at a web site near you. It’s my site and I made the movie. Monika, a 29 year old crossdresser and Sheri, a 52 year old house wife.

This is a real life older woman, crossdressing fantasy come true. Hasn’t everyone of us masturbated while imagining an older woman catching us in our panties or maybe her panties? If you see this movie and don’t come at least twice then I’ll have to take away your crossdresser’s merit badge.

Here’s the full story line.

Read the rest of this entry »

Cheryl’s First Sissy Milking

Cheryl is a 56 year old woman that my wife and I met at sex party.  We chatted with her during break and came to find out she has a special fondness and attraction to boys and young men that cross dress.  We talked a lot about this with me promising to introduce her to my 25 year old friend Monika.  Monika has been wearing girly clothes since she was 9 years old and considers herself a girl. Monika lives her life as a sissy often wearing dressed up as a little girl in ruffled panties and frilly party dresses. 

Monika misbehaves often and likes her punishment firm and committed

Monika is sweet and adorable and yet gets wonderfully hard and long when she’s excited.  We made a little movie together, yet to be seen, where I as her mother punished her for showing the boys her panties in school that day.  She got really hot playing that scene and very hard too.  We didn’t have sex but I have continued to remember and admire seeing her swollen cock sticking straight out, proudly and grandly.

I brought them together, for the first time to make a short movie acting out a pantyboy, crossdresser fantasy.  You know the one.  When the older woman slides a pair of panties up your legs admiring your hard cock along the way.

Cheryl dressed her in a pair of white nylon panties.  After checking the fit, both front and back, slowly and carefully, Cheryl sits Monika on the couch and plays with her cock for the longest time and them milks her until she comes.

I loved seeing Monika with her white panties pulled down while Cheryl  pumps her until she squirted.  Cheryl loves old fashioned underwear.  She was wearing a white full vintage slip.  It had lots of lovely lace and is sheer enough that you can see her white panties, garter belt and stockings right through it.

If that happened the first time they met just imagine the second

The next movie they make will be with Aunt Cheryl feminizing and dressing Monika and then sucking her penis through the panties.  This will be the first sissy cock she has sucked and she told me she is really looking forward to taking Monika’s cock out of her panties and right into her mouth.

Auntie Masturbates Her Nephew in Her Panties

I met Sheri at an erotic art exhibit in San Francisco. We were both looking at the same work of art. A photograph of a soft penis tucked away and barely visible in the sheer pink panties.

“What do you think?” I asked her. She laughed and said “It reminds of me of my nephew.” “How, so?” I asked back.

He crossdresses and I know that he gets into my panty and lingerie drawers every time he visits.” “Does that upset you?” “Not really” she answered. ”I got a peek at him trying on my panties in front my bedroom mirror and he actually looked kind of cute. I also know he has a special fondness for my panties. I often find them in the hamper, wet and sticky after he visits. Maybe it’s time for him and I to have a talk about it. I’d rather he wears my panties around the house instead of being ashamed and secretive.”

“What do you do?” she asked me and I told her I had an erotic web site for crossdressers. She was curious and asked a lot of questions and when she found out I photographed and filmed all my own material she was even more interested.

“I’d love to shoot you and your nephew some time” I was sure she would say no but she didn’t. “Sounds very interesting. Let me think about it and I’ll call you”

I gave her my card never expecting to hear from her but she called in about a week. She said she had a long talk with her nephew about his crossdressing and they bought thought it would be good for him to be open about his panty fetish.

They showed up on time and I offered them something to drink while we talked about the session.

She was 52 with a nice full body and lovely short blond hair and he was 18, talk with long brown hair. The both seemed a little nervous but anxious to get going so I told them about the first scene of her putting his panties on.

I dressed her in full cut panties, stockings, garter belt, white lacy bra and a vintage full lace trimmed slip.

I asked her nephew to put on a garter belt and stockings and a sheer robe as a little cover up. They dressed in separate rooms so when the came into the studio it was the first time they had really seen each other. His eyes got big as he looked his auntie up and down. From what I knew he had never actually seen her dressed like this. His cock started to stiffen and it was clearly visible through the sheer robe. She and I both noticed it. She smiled and walked over to him and gave him a big hug. I heard her whisper to him. “I’ve been hoping this would happen sometime” and kissed him quickly on the lips.

The ice was broken and I knew that it was important to get into shooting mode quickly.

“Let’s being easily and gently”

I gave them directions and began to shoot.

She sat on the couch and he stood directly in front of her. I took of his robe and he was still swollen in his panties. I wanted them both to get over the next hurdle on being intimate with each other so I asked her to put her hands on the waistband of his panties and I started taking pictures.

He was watching as she began to slide her hand over the panties, not yet touching his cock. “Touch him” I whispered and she did. She slid her hand onto his hardening panty tent and a smile came over her face. She was stroking his pantied cock looking up into his eyes. They were both entering into a new world of crossdresser panty love.

It was along wonderful session. They came to know each other well. She understood more about his panty fetish and what he like to do to satisfy his panty needs. He discovered that there were some women that really found men in panties and panty play extremely erotic.

They were both satisfied.

“Aunt Lisa Panties Her Nephew”

Aunt Lisa always wore the same thing around the house. As soon as she got home from work she would rush into her room, throw her purse on the bed, reach down and scoop the dress up and off her body.

She was just beginning to show the first gray hairs of a beautiful maturing woman. She was lovely and moved with a gracefulness that only severed to enhance the sway of her wide hips and full bosom.

The slip she was wearing today was like so many others she wore. It was a full slip. White, nylon with a sweet lace trimmed bodice with little satin bows where the cups meet. Her slips are always sheer, feminine and tight. Especially across her glorious ass. Tight and sheer enough to, clear see the outline of lace trim on her panties and the wide full gusset seams. Dark stockings against pale fleshy thighs and white of her slip was pure satisfaction for the most discriminating full cut panty and slip fetish.

Hearing soft moaning come from the hallway she when to see where and who it was coming from. She was worried that her nephew, David might be sick.

She stopped in her track as soon as she opened his bedroom door and saw him on the bed. He was obviously masturbating, which didn’t surprise her. After all he was a boy after all. What shocked her was that he was wearing one of her slips and rubbing his cock with a pair of her panties and holding another pair over his nose.

When he looked up a saw her he screamed and rushed to cover his hard cock and his overwhelming embarrassment.

What stunned her the most was her won reaction. She had always found David cute and very warm. He was growing up now and his sexual nature, passions and desires were taking form.

He was so excited wearing her underwear that she felt compelled and excited to help him explore all his desires.

He was still red from embarrassment and trying to hide his ever hard cock behind the sheer lace hem of her slip.

She slowly and provocatively walked into the room and sat down next to him, their slips making that lovely swishing sound. She gently pushes him down on his back, takes the panties from his and slowly begins rubbing his cock until it’s rock hard, red and straining for more. Looking him in the eye she says “You love my panties, don’t you. Yes, you don’t need to say anything, at all.” With that she took off her panties and lovingly placed the gusset directly over his nose. “Breath deeply, my sweet, breath deeply inhale me”

In three breaths his cock convulsed as she stroked him into a huge, wet, beautiful, high spurting, orgasm

She scooped him into her arms, still gasping for breath. Lisa held him tightly to her bosom, rocking him gently. As his breathing slowed she reached into her slip and bra rolling her breast into the open. Her nipple was hard and red and felt relief when she eased it into David’s open mouth.

Milked at Bedtime

I went to bed that night wearing only my full cut pink panties with the white lace trim around the legs. I love Dixie Belle panties because these are so smooth and they have a lovely wide gusset that’s very comfortable.

Mornings start earlier for me than my wife so I often fall asleep while she is reading next to me.

I was sleeping soundly on my side when I felt her curl up next to me and nuzzled my next from behind and slid her hand into my panties and gently hold my cock. She did this often when we fell asleep together but this time was different.

She began to gently run her fingers around the tip of my cock and coaxed it into an erection. It didn’t take long foe me to realize that she lube on her hands and fingers and was planning on milking me in my pink nylon panties.

Her rubbing and stroking got more intense and I began thrusting my cock into her hand hearing her words.

“Are you my little sissy husband in panties? Is that what your are? A pantied sissy? You’re my sissy in pink panties aren’t you? Say yes, my sweet. I want to hear you tell me that your my sweet, little, pink pantied sissy and that you love being milked. That’s right isn’t it? You love being milked in your panties and coming in them for me, don’t you? OK my love, It’s time to squirt and fill your panties for me, come on, yes. That’s it. Squirt in your panties for me. Yesssssssssssssssss

We fell in to deep sleep with her fingers curled around my sticky, messy cock.

I love my wife. My wife loves me