A Sissy Cuckold and Her Boyfriend

This is a real difficult blog post for me.  i'm struggling with what to say and how to say it for a couple of different reasons. 

i had my first real "date" with Jake yesterday.  By real, i mean that finally we had the opportunity to be intimate with each other.  Both of us were very nervous, even though there was no chance that Diane would come home.  In fact, She told me early Friday morning that She would be out of town for most of the day at a meeting.  This seemed to make Jake a little more comfortable but it was still our first time together so there was a natural nervousness. 

He got over it pretty quickly though, and that made me feel real, real good.  He knew i was wearing panties and asked if i was wearing anything else.  i told him i wasn't so he asked me if i'd like to put something pretty on for him.  Of course i agreed but in my mind i was hoping he would be a little more forceful and demanding, TELLING me to put something on instead of just asking.  Maybe in time.

i came back in a short yellow nightie, kind of like a babydoll but not quite.  i also wore white high heels and even had a faux pearl necklace on.  Jake just loved it.  He had me model it for him.  i stood in front of him and in my most feminine and coquettish manner, twirled around, curtsied and bent over so he could look me over.  Things just got better from there and i pulled me close to him and put me on my knees while he sat on the loveseat in our living room. 

Soon after i started this blog, i decided that i wouldn't get into overly graphic sex scenes.  i wanted to keep it more R-rated than anything else.  That's one of the things i'm struggling with.  How do i keep it R-rated and still be able to convey the intimacy that took place between Jay and i?  Or, do i abandon that philosophy and tell everyone everything that happened, in explicit detail?  For now, i hope you can read between the lines.  i will tell you that i serviced Jake three times with my mouth, and he promised to come back for more.

i was also happy that my submissive side was more than satisfied, particularly since there was no reciprocation on his part.  It's just me, but i don't look at a Dominant Man and expect him to go down on me.  i'd enjoy it with another sissy, but not a Real Man.  Instead, Jake wanted me to masturbate in front of him.  i did, and did it in my usual sissy way.  He just loved that....thought it was so "F*&%(^ hot" - his exact words.

When he left, he told me to "be a good girl" and he kissed me.  That was totally awesome.

Diane got home a little later than usual last night due to her out of town meeting.  She called and told me to make sure i was dressed pretty for Her, something casual but feminine so we could enjoy a glass of wine together.  After pouring the wine and setting out some cheese and crackers, She asked me how my "date" with Jake went.  She wanted to know absolutely everything, down to the smallest detail.  Diane took it all in and really made me feel comfortable.  Her encouragement and support was really uplifting. 

When I asked Her how Her day went and Her out of town meeting, the answer I got shocked the heck out of me.  Her out of town meeting was actually a hook up with Brian.  "I didn't want to tell you about it this morning because I figured you were nervous enough about your first time with Jake" She said. 

"It's my turn to tell you about my date" She said with a big smile on Her face, "you can also ask me anything you want."   She went on to tell me all that happened that afternoon with Brian.  i didn't ask any questions.  i didn't have to.  She was very explicit.

When She was done telling me about Her date, She told me to follow Her to the bedroom.  "I could use a nice licking" She told me.

As i began to worship Her, She asked me "Do I taste different?" 

She did and i told her so. 

"Do you like it?" She asked.

"Yes Diane.  i do." i told Her.  To be totally honest, i loved it. 

"It was nice that we were both with our boyfriends today" She said, not expecting an answer.