"I think it's just cause your not used to wearing a nightgown and the pantyhose may be feeling different than the tights. How do you like your pantyhose anyway?" Amanda asked trying to change the subject.
"I was a little hesitant mom but I absolutely love them! It's almost like I'm not wearing anything. I like the feeling of the air flowing under my nightgown also. It feels cool especially when I do this."
Just then Jessie twirled around quickly several time as his nightgown ballooned up from the airflow.
"Wow, look at you. Maybe you should be taking up dancing," the ladies amused at his performance.
"What did you buy mom?" Jessie asked with a sense of excitement.
Amanda handed her son the bag noticing his curiosity.
Jessie pulled out some of the contents. He noticed three bras with underwear attached in matching colors.
"Matching bras and underwear mom?"
"Yes dear, I was lucky to find some underwear that came with the bras so that you match." Amanda replied as she made little attempt to hide the bra and panty sets. In Jessie's state of mind she knew she would not have to explain too much.
She wondered how he did not connect the dots and figure out that he was indeed wearing panties. The new sets she bought were unmistakably feminine with lacy ruffle around the legs and little flowers at the top.
"I like the way they look mom…pink, light blue and yellow."
Jessie reached into the bag and pulled out 4 packages. He looked at the front and noticed a woman's lower half encased in nylon. He read the header on each package which said "Hillard and Hanes Pantyhose". The packages read "Nude", "Suntan", "Black" and "White". He also noticed labels that said "sandal foot" and "sheer to waist".
"Mom, I wanted tights not pantyhose. Girls wear pantyhose and I'm not a girl so forget about it. Take them back and get me tights."
"Sweetie, these are the tights I was telling you about." His mom countered, "Pantyhose are just a name for tights which have thinner material. Remember what I said about wearing these and having no-one notice? Don't get turned off by the name Jessie, if you don't love them we can take them back. My feelings won't be hurt but at least try them on Ok?"
Jessie thought about her offer. He knew he was opposed to wearing pantyhose cause boys don't wear pantyhose, but they did look lighter than his heavy tights. The colors were cool too and if no one could tell he was wearing them then what difference did it make.
"Ok mom, I'll try them on at least, but if I don't like them I'm not gonna wear them." Jessie stated adamantly. "What does the sandal foot and sheer to waist mean?"
"Well the sandal foot does not have the re-enforced toe and it is designed for you to wear with open toed shoes. Then you can show off your pretty toenails. Sheer to waist means that there is not a control top panty to pull you in as much on top. You wear sheer to waist when you have on clothes that show a lot of upper leg. If you were to wear the control top pair I got you with shorter shorts people would be able to see the darker shade from the control top and that's not attractive."
"Wow, that's a lot of information mom"
"There's a lot to know dear. There's one more thing in the bag" said Amanda.
Jessie pulled out a pink charmeuse silk garment that had spaghetti straps like his camisole tops but was much longer. It had tiny lace stitching around the triangles that would cover the chest and a slit on the sides of the bottom of the garment. He held it up to himself and noticed that it extended down to just below his knees.
"Mom, what's this? It's way too long for me. How am I going to tuck this into my pants?" Jessie questioned..
"Oh dear, it is not supposed to be worn under your clothes. I bought this for you to wear to bed. Since you love wearing your tights so much I figured you didn't need pajama bottoms. The tights or pantyhose are fine for you to wear but would get too hot if you also wore pajama bottoms. At the same time, nylon is see through and I don't think you want to be walking around with your underwear showing through dear." Amanda joked.
"You can wear the 'nightgown' to bed and it will cover up everything that needs to be covered up but at the same time it will keep you cool. What do you think?"
His mom made sense. It would get uncomfortable wearing his tights under the pajama bottoms. He could just wear a top, underwear and tights but he would be too embarrassing if his undies showed through. At least the long garment would cover that up.
"OK, I'll try that on also. Dang, your gonna spoil me mom!" Jessie stated feeling like he was king for the day.
Amanda left the room and let her son explore his new clothes. Nightgown today…dresses tomorrow she wondered?
Jessie looked over his new clothes. He felt a somewhat awkwardness and slight embarrassment as he looked over all the frilly, lacy items. Something felt "off" about this whole situation but he couldn't place it. Maybe it was just the fact that he hadn't had any new clothes for a while and was feeling a bit overwhelmed.
"Well, I might as well try some of these on before I go down to eat."
Jessie decided that he would try on the pink bra and panty set and the sheer to waist nude pantyhose.
He stripped out of his clothes and undid his bra. As he put on the pink bra he tried to retrace the steps that Ashley had shown him. Fasten the clamp…adjust the straps…pull the flesh to sit in the cups. That wasn't so bad he thought. He noticed the dainty flower sewn into the center of the bra and found himself amazed at the detail. He also was a little taken aback by how the bra molded his two mounds into two round globes that jiggled lightly when he moved. It was only a matter of time before he was
back to normal and he just had to deal with it for now.
He pulled on the panties next. These were a bit lower cut than his last pair and they also had a flower stitched into the top center.
Jessie pulled the pantyhose out of the package and wadded them up. He slid them up his legs and pulled the panty over his hips and waist. He looked at himself in the door mirror and admired how nice his legs looked in the pantyhose. His mom was right. He loved how delicate and light the nylon felt compared to his tights. He held up the package and compared his legs to the woman's on the label. He struck the same pose as her with his right leg bent slightly crossing his left.
"Dang Jessie, you have pretty nice looking legs," he said to himself. "She ain't got anything on me!"
He was oblivious that he just compared himself to a picture of a woman's legs in pantyhose. He was pretty proud of the fact that he looked pretty darn good though. He also saw that with the thinner material he could clearly see his panties through the nylon.
Next was the nightgown. He stepped into the garment and began pulling it up. About halfway it got very tight and he could not bring it any further. It was stuck around his curvy hips. "What the heck? I gotta work out some more."
He pulled the garment down and instead lifted it over his head and slipped it down around his body. It fell just below his knees.
"That's better" he thought. He did a little twirl and relished the air flowing underneath and between his legs.
Jessie once again looked in the mirror and beheld something very strange. It was him but he looked different. Something was not as it should be. He was trying to figure it out when he noticed that his bra straps were visible. Was that right?
"Hey mom!" Jessie yelled down. "Do I wear a bra with my nightgown?"
"No dear," Amanda replied with a little giggle, "you don't need to wear the bra to bed."
Jessie removed the bra and laid it on the bed. He went downstairs to eat.
"My My My don't we look all comfortable," Susan stated as she beheld her grandson.
"Mom bought me some new clothes so of course I had to try them on."
"Oh dear, you better be careful walking around barefoot in your pantyhose. You don't want to get a snag and believe me it happens easy with such delicate nylon," Susan advised Jessie. "Amanda, did you buy Jessie any slippers? He is going to get a run in his pantyhose in no time if he keeps walking around without protection."
"I forgot. Here Jessie, you can burrow my slippers until I buy you some," Amanda replied as she handed Jessie her soft white slippers.
"Thanks mom. Does something not look right about what I'm wearing? I get the weird feeling that there is something that is not normal here." Jessie asked still feeling a little off.
"I think it's just cause your not used to wearing a nightgown and the pantyhose may be feeling different than the tights. How do you like your pantyhose anyway?" Amanda asked trying to change the subject.
"I was a little hesitant mom but I absolutely love them! It's almost like I'm not wearing anything. I like the feeling of the air flowing under my nightgown also. It feels cool especially when I do this."
Just then Jessie twirled around quickly several time as his nightgown ballooned up from the airflow.
"Wow, look at you. Maybe you should be taking up dancing," the ladies amused at his performance.
The three sat down for dinner and talked about the days events and made small talk over the great meal.
Jessie helped clean the table. He was so much more help around the house lately. He washed the dishes, made his bed everyday, helped vacuum. It was so nice having him around now.
As he carried some plates to the sink his hand slipped. He dropped two of the plates and they shattered as they hit the tile.
"Crap!" Jessie exclaimed as he put the rest of the dishes into the sink. His mom knelt down to pick up some of the pieces. Jessie joined her bending over to pick up some of the large pieces.
"Don't worry about it Jessie. We have more of those plates and accidents happen."
Amanda's eyes glanced at the top of Jessie's nightgown. With him bent over she could see down his top and what she saw amazed her. As he moved back and forth to pick up the pieces she could see his two breasts hanging down and swaying slightly. They had grown large enough to dangle down. She glanced away feeling it was rude to look at her daughter's
breasts.
Her "daughter's" breasts? She caught herself referring to Jessie with a feminine pronoun.
His transition had just taken a major turn.
