Sissy cross dressing phone sex | Debbie | with Ms. Jennifer 1-877-368-7505

Panty boy phone sex 1-877-368-7505

I enjoy sissy cross dressing phone sex, especially with Debbie.  I have been helping transform her into the perfect girl. I have been posting about her recent changes. However, I have a lot to tell you about how she started to transform to become the beautiful girl she is now.  She has started taking birth control pills, but before this advance, there were many steps leading up to this. I will go back a bit, and tell all you lucky readers, some of the issues she has faced and maybe some solutions. Be sure to check back, she has so many updates and questions about being a girl, I would not know where to begin to share all this.  I never realized how much you need to know, if you want to be a girl!

A while back she said:
Ms. Jennifer, Thank you for the advice on dressing up for the first time.  Before my bf arrived, I called him and informed him to get some lubricant and I also mentioned some lipstick.  He did.  Afterwards, I told him, if he wanted me to do so again, I would need more lingerie and clothes.  He agreed and said he would get some more.   I will call to inform you how it all went. ( I had suggested these items, and then she asked her bf)
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Debbie then had a date  and here is an update:
Dear Jennifer: The date went awesome and awkward at the same time.  My bf’s sister brought over a new type of lipstick for me to use…it was the one where I basically paint my lips.  She brought over a couple different colors but she knew the dress I picked out and the shade I wore last night was a pink color.  The dress was a pink floral cocktail dress.  She informed me it was a cocktail dress.  It was all pink but with a floral lace like design from the waist up.  I had to wear pantyhose with the  dress…no garters.  The dress came to above the knee.  I felt very feminine in it.  (Double date with bf and his sister and husband) It was awkward with her husband at the start but as the night ended it was okay.  If my voice was more feminine sounding it would be easier.  We spent the night talking, listening to music, tv and playing some board games.  Some quick thinking on sister’s part saved me from meeting the parents, they were going to stop over and Kendra had to inform them to postpone it.  whew…. my bf sure loved it.  When we got back to my place, I had to quickly change from pantyhose to garters and nylons.  We also tried a new position at the start..me on top sliding it inside me.  That position takes a lot of work from me, I still prefer being on my back with pillows propping my male pussy up.  I so enjoy watching it go inside me. I find that 3 times a night is the norm for him.  The 4th time, he experiences extreme sensitivity in his penis and we are done for a few hours. (Debbie ordered a pussy panty) she said: No the vagina/pussy panty hasn’t arrived yet. Love Debbie Good morning Jennifer, I found I have a couple gripes about dressing up which are small gripes but annoying.  One, I hate getting “runs” in nylons or pantyhose  so quick.  Second, I found wearing lingerie in bed “very warm sleeping in”.  Nylons, garter, gown, bra under the  covers gets very warm in addition to having him all over me. (I told her you paint the runs with nail polish to stop them from running)

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