The Softening of Jessie - Part 25

"Ok, I was wrong I guess. Thanks for letting me borrow one of your dresses Ashley."

Jessie gave her a big hug. He was so lucky to have such a great friend.

"Damn you are sexy!" Ashley replied as she reached under his dress and pinched his ass.

"Hey! Stop that!" Jessie yelled embarrassed and a little surprised at how easy it was for her to reach up under his skirt.

The Softening of Jessie

Part 25

By AshleyTS


 
Ashley pulled a denim skirt out of her bag followed by a light blue colored dress.

"What do you think Jess? The skirt is made out the same fabric that your jeans are made out of, so it's not a big change. The dress, on the other hand, would look great on you."

Ashley held up both of the garments to show Jessie. He was having second thoughts about this. He never had worn a dress or skirt before and although he couldn't think of a reason why he hadn't he was still very standoffish.

"I'm not so sure about this Ashley. It somehow feels weird to be wearing your clothes."

"Look, if anything is weird about this it is the fact that I'm being such a nice person to you. I'm usually very possessive of my clothes so you should be grateful I'm willing to share sweety. Now which one girl?"

Ashley once again held up the garments trying to put a little more pressure on her feminine friend.

"I don't know. I guess I could try the skirt on. The dress is really weird and I'm not sure how I would feel in it since I never have worn one before."

"Honey, look at what you wear to bed every night. That is basically a dress. The only difference is that this one is for wearing outside. It would look great on you. If you don't like it you can try the skirt on ok?" Ashley promised.

"Uhhh, yeah...Ok. How do I put it on?"

"Just step into it," Ashley replied as she lowered the dress to the ground and guided his feet into the opening.

"I'm just going to lift it up now," she said as she raised the dress up his pantyhose clad legs and up around his torso.

"Now put your arms through the straps."

"Good girl! Now I'll just zip it up in back and viola! You're done!"

Jessie didn't know what to think. The dress was very form fitting around his upper body and midsection and then flared out loosely. It was short...real short and came to rest about 8 inches above his knees. The dress was light blue with a white ribbon that wrapped around the upper midsection just under his breasts and tied in back to form a bow. The straps of the dress were very thin as well. It did somewhat remind him of his nightee.

"How do you feel Jess?"

"A little wierd. It feels really short. Should I be wearing this even? You don't think it makes me look girly?"

"You look great sweets. I wouldn't have given you such a short dress if I didn't think you could pull it off. I mean look at those legs! You have very attractive legs, so why not show them off a little? Is the dress too girly? I don't think so. I mean I wear that dress a lot and I never get any comments that it is over-girly. Plus it's blue so it won't hurt your male ego to be wearing an unmanly color."

Jessie looked himself over again and it did feel nice to be dressed up a little. He looked down at his legs and admired the shimmer of the nylons. Ashley was right; he did have some killer legs!

"Ok, I was wrong I guess. Thanks for letting me borrow one of your dresses Ashley."

Jessie gave her a big hug. He was so lucky to have such a great friend.

"Damn you are sexy!" Ashley replied as she reached under his dress and pinched his ass.

"Hey! Stop that!" Jessie yelled embarrassed and a little surprised at how easy it was for her to reach up under his skirt.

"Sorry Jess, I couldn't help myself" Ashley joked. "At least you had panties on.

"A couple things though Jess. One, we have to get a different bra on you because I can see the straps and two you should wear a slip under your dress. It will keep your skirt from clinging to your pantyhose."

"Okay, but I don't have any of those."

"Well you are in luck today girl!"

Ashley pulled out a half slip and a strapless bra.

"By the time I give you my clothes I'm not gonna have any for myself," she joked.

She unzipped Jessie's dress and let it fall to the floor.

"Now let's get that bra off."

"Hold on. Close your eyes."

"Oh come on Jess! I have seen breasts before you know. Besides you are going to have to have me help you put the strapless on so whip that baby off."

Jessie reluctantly unhooked his bra and removed it. His breasts gently jiggled as he stood there topless in his pantyhose and panties.

"Those are quite amazing Jess. You'll learn soon enough that they will get you anything you want...very powerful."

Ashley wrapped the strapless bra around his breasts and adjusted it so that it fit comfortably.

"See? No straps so that your dress will look amazing. Now step into the slip honey."

Jessie pulled the slip up. It was very lacy he thought. Lacy and very pretty and the way it felt against his legs was electric.

With that he pulled the dress back up and Ashley zipped it up.

"Wow! You look great now! No bra straps see?" Ashley showed Jessie his reflection.

"Yeah. It looks really good," he replied as he admired the delicate garment that wrapped his body.

"Now let's complete the outfit."
 


To Be Continued...

 



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