Just Like a Woman - My First Time

i got to meet with Jake this week (at his place no less) and it was an intensely sensual and pleasurable meeting.  Jake's wife was gone for a few days staying with her mother and he had the whole house to himself.  There was something very naughty about him taking me into the master bedroom and telling me i was going to be his "wife for the day."

The deep purple short nightgown he bought me as a surprise got me hard instantly.  Jake joked that i certainly didn't look very feminine with my little erection and suggested i do my best to hide it.  It was difficult, but i tucked it between my legs for him while modeling the nightie and he got a laugh out of that.  The black lace on the gown made me feel more sexy than sissy-like and i think Jake felt the same way.  i was soon on my back on the big bed with  my smooth legs wrapped around him as he lay on top of me.  i was swooning and wanted him.

Jake was as hard as i'd ever seen or felt him.  i wanted him in my mouth, but part of me wanted him inside of me even more.  He could tell and said "Do you think you're ready?"  As much as i had been thinking about this moment, it was another one of those things that caught me by surprise.  i wasn't sure what to say and i think he was uncomfortable with the silence and finally told me it was fine if i didn't want to.   But i did want to.

"Can we try?" i asked him.

"Of course.  We can stop anytime" he said as he lay on top of me and stroked my thighs, "just say so."

Well, after plenty of foreplay (really the best part), a large amount of lube, some discomfort, and plenty of tenderness and understanding on Jake's part, i took his beautiful cock in my bottom.

It took awhile before he entered me fully.  In fact, he let me control how deep he went, instructing me to back onto his cock when i felt comfortable enough.  i was on all fours on the bed and i just loved feeling the tip of his cock pressed up against me.  The most difficult part, much like taking Diane's strap-on, was the initial penetration.  i relaxed after awhile and enjoyed it immensely.

Jake used a condom of course, but knowing he came from making love to me that way drove me wild and i had an ograsm of my own, without even touching my own penis.  i felt like i had an orgasm "just like a woman."  In fact, those are the terms Jake used when he told me i was cumming "just like a woman."

When it was all over, i felt different and still do.  It's hard to explain exactly how i feel different.  Part of it is as if i've taken a huge step towards becoming more like a woman, while still retaining my physical masculinity.  There's a huge emotional component to it also.  i seem to feel an inner glow that's difficult to explain, a feeling of fulfillment.  i can't wait to do it again.