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.