The Softening of Jessie - Part 6

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"So we are in luck Jessie. I found some tops for you to wear under your shirts. They should fit tight so that no one can tell they are there and yet they are very soft which will help with your swollen chest. I also found you some underwear that should fit you better. Here's the fun part though...I was lucky enough to find them in matching colors. I know how you liked your old underwear to be in different, cool colors so I think you may like these," Amanda explained hoping Jessie would be fine with his new undergarments.

She knew that he did like his underwear in different cool colors meaning he liked black, grey, navy blue, and forest green. What would his take be on these softer colors? Would he accept wearing panties?

The Softening of Jessie

Part 6

By AshleyTS


 
"Mom, you must see Jessie's nails! Not only did he do a beautiful job on my toes and fingers but he also glossed his toenails with guess what? Yep, pretty rose!"

"That is wonderful dear," Susan replied, "He is progressing as we had hoped. All that anger, mischief, and all around bad attitude is giving way to a beautiful, blossoming child."

"I just had the best time with him since...well, since I can remember. We actually bonded which is something I had all but given up on," Amanda gushed with pride.

"His proportions have changed mom. His hips have grown too big for his underwear and I'm wondering how much longer his pants will fit him. The only thing that is saving him a little time there I think is the fact that he likes his pants baggy. I told him I would buy him some more camisoles and some underwear that would fit."

"Oh dear, I have just what he needs," replied Susan as she pulled open her drawer which contained an ever growing collection of girls clothing. "These will be perfect for him. There are 5 sets in all and I just think he will be tickled pink with them."

Susan handed Amanda 5 packages of camisole/panty sets each in matching colors. The colors included lavender, powder blue, peach, pink, and yellow. The packages read "Fruit of the Loom Just for Girl's Cotton Camisole and Panty Set".

"Mom, these are great! I think I had better open the packages though, since I am not sure if he wants to put on anything with the words "Girl" or "Panty" on it just yet, hehe! These are very soft and should ease the sensitivity in his chest nicely," Susan said as she lavished over the delicate fabrics.

They were quite lovely indeed with spaghetti straps on the tops which led to the top which was stretchy cotton that would cling to Jessie's chest. The camisoles looked as if they would end just above the belly button and had a very thin lace weave across the bottom matching the color of the top.

The panties were so pretty she thought. They were low rise with thin lace weaving around the band on top and around the leg holes.

Jessie went up to his room after the show was over and sat on his bed admiring his nails. Man, he had outdone himself! Picasso eat your heart out!

As he sat on his bed reading through Hot Rod magazine he was suddenly reminded of his favorite pastime...masturbating to the hot girls of the magazine. He thought to himself that it had been quite a while since he had pleasured himself to the scantily clad girls of the car magazine. With that, he walked over to his bedroom door and quietly locked it. There would be no unwanted interruptions here. He went to the bathroom to grab a handful of toilet paper and positioned himself properly on his bed. It had been long enough that he knew this would be a great load. Why was it that he had forgotten about masturbating for at least two weeks
now? It was so unlike him he thought. Oh well, this session will make up for lost time, haha!

He turned to page 32...Heather, the car model, was wearing a tight black top which accentuated her full breasts and left little for the imagination. Her shorts were black as well and made out of a thin nylon material that clung to her curvaceous rear end. He began stroking himself...this was gonna be good!

A minute passed and he could not get fully hard. What the heck?

He focused more intently on the girl...she really was stunning. He stroked harder yet and disappointingly still could not get fully hard. Intent on not giving up, Jessie stroked faster and faster until he could feel his orgasm coming. The big eruption was about to happen...hard penis or not. He tensed up but the hard, spurting release of white fluid did not happen as expected. Sure the release was there...in fact it was incredible, but it was different.

His semi hard penis did not spurt out a thick, white fluid. It instead released a watery, clear liquid that oozed out in one single steady stream through a rubbery shaft.

"What the heck was that??" Jessie thought.

Just then Jessie heard a knock on his door.

"Sweety, it's mom. Can I come it?"

"Ummmm, give me a minute ok? I'm in the bathroom." Jessie nervously replied as he ran to the toilet and flushed his watery tissue down. He composed himself and unlocked the door.

"So we are in luck Jessie. I found some tops for you to wear under your shirts. They should fit tight so that no one can tell they are there and yet they are very soft which will help with your swollen chest. I also found you some underwear that should fit you better. Here's the fun part though...I was lucky enough to find them in matching colors. I know how you liked your old underwear to be in different, cool colors so I think you may like these," Amanda explained hoping Jessie would be fine with his new undergarments.

She knew that he did like his underwear in different cool colors meaning he liked black, grey, navy blue, and forest green. What would his take be on these softer colors? Would he accept wearing panties?

Amanda laid out the garments on his bed. Jessie held up the tops, and then picked up a pair of the panties.

"Mom, where is the fly on these?" Jessie questioned.

"Honey, there are no fly's on these underwear. Because of your shape I could not find your regular underwear in your size proportions. Think of these as "speedos type" underwear. You know...the kind that MEN wear that are professional swimmers?" Amanda was so proud of how quick she was on her response...professional swimmers ha!

"Yeah, I know what you mean mom. That guy who won all those gold medals and stuff...he wears these kind of underwear?"

"Yes dear. All those pro swimmers wear speedos that don't have a fly. Maybe we could fit you back into your old type of underwear if you worked out some," Amanda teased.

"Yeah, you've got a point. I really do need to get in shape. I never remembered my butt being so dang big. I am however going to be wearing underwear made for only the fastest of swimmers in the world, haha!" Jessie joked as he continued to inspect his new underwear.

Jessie got off the bed and gave his mom a big hug.

"Thanks for buying me new underwear so quickly mom. My old stuff was so uncomfortable. I hope this new stuff fits me better."

Amanda was touched by his gratitude and surprised he did not mention the feminine colors.

"You're welcome son. That's what moms are for after all. Try them on and let me know how they fit and feel. If you like them I will get more and if you are worried about your rear end getting too big then I think I can help with that too. I have some great exercise tapes that will slim down those problem areas in no time. Just let me know when your serious and we'll see if you can keep up with me and grandma haha," Amanda challenged her son playfully.

"I may take you up on that offer. I think I can keep up haha. I did run rings around you when it came to painting nails...I may have to put you two in your place with exercise as well."

With that, Amanda let Jessie be alone to try on his new intimates in the privacy of his room.
 


To Be Continued...

 

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Comments

Typical Male

The guy is so big ego that he cant even notice his Mum is putting one over him ! Does it sound extreme? I dont think so - I have known guys like this. He he !

Briar

Briar