This is a true story of how my Mom feminized me as a teenager. She had caught me wearing her pantyhose the summer before seventh grade. I got the surprise of my life the first Sunday of junior high, when she started encouraging me to wear them, and then it was all downhill from there. -- Tracy
Sunday morning, I saw Tina at church, and she smiled at me when our eyes met. After church, she stayed a few minutes after the choir dispersed, and came up to me in the choir room.
“So are you feeling better today?” she asked. “Did you get your constipation problem taken care of?”
“Mmmm-hmmm,” I replied, blushing.
She continued, “I was going to ask you if you’d like to get…. dressed up and go shopping. Erin is going to be at a friend’s house all day Tuesday. I thought maybe we could go shopping and then maybe do lunch.”
I tingled with excitement at the thought. “Sure,” I said. “Where do you want to meet?”
“Why don’t I just pick you up?” she asked. “You live on Applewood Street, right? That’s not very far out of the way. Ten o’clock alright?”
“Sure,” I smiled. “I can’t wait.”
On Tuesday morning, I got up early and shaved my legs. I got out my new K-Mart Soft Smooth and Sheer pantyhose and put them on. I was going to wear my macramé wedge sandals and they were the only nylons I had that were sandalfoot. After putting them on, I put on my robe and went in the kitchen and had a bowl of bran cereal for breakfast.
Afterward, I went back in the bedroom and was admiring my smooth, sexy nyloned legs and feet in the full length mirror. I pulled my black pinstripe slacks on over my hose, followed by my black sweater. I stood up and got my beige macramé sandals out of the closet, and sat back down on the bed. Slipping them on my hosed feet, I did up the buckles, and then stood up and modeled in front of the mirror again. My feet looked so smooth and perfect in my sandals and sandalfoot hose!
I went out in the living room, turned on the TV and sat on the couch, enjoying the feeling of being all dressed up in girl clothes. A little while later, Tina pulled up in the driveway. I saw her walk around to the front door and I opened it before she got there. She had on a brown sweater, denim miniskirt, tan hose, and brown clogs. She looked so hot!
“Hi,” she said as she came in the door. “Ready to go shopping?”
“Of course,” I said. “Wow, you look great!” I said, staring at her gorgeous legs.
“So do you,” she said, staring at my feet. “Those sandals are cute. I wore my clogs cause I thought they would be easier to slip in and out of when we’re trying on shoes.”
“Let me get my purse and some money and I’ll be ready.” Grabbing my purse and my wallet and keys, I walked back into the living room as I stuffed them in my purse. We walked out the front door and I locked the door behind me.
We got into her car, and I couldn’t help staring as I watched her fold her shapely nyloned legs under the steering wheel. As we drove off, she said, “I didn’t know what to wear. I didn’t want to ask you what you were going to wear at church in case someone overheard us. I thought I’d wear a skirt in case you did too.”
“Well, actually, I don’t have any skirts of my own, just slacks. I guess I could have borrowed one of Becky’s though. It didn’t occur to me. I’m not that brave yet,” I giggled.
“That’s OK,” she said, patting my knee, “whatever you’re comfortable with. So you got your poo problems resolved?”
“Mmm-hmmm. My boyfriend came over that afternoon, and sensed that I wasn’t feeling well. I told him I had bought some Correctol because I was constipated, and wondered if I shouldn’t have gotten an enema instead. He suggested that maybe it would help me go if we had,” I said, blushing, “sex in my butt. So he gave me an enema with his wee-wee,” I giggled.
“Did that work?” Tina asked.
“Yes,” I replied. “I had a HUGE BM afterward, and it was really easy. His semen made it really slippery and slide out really easily.”
Tina smiled. “Tom and I have done it that way before and it had the same effect on me. Back when we were still having sex,” she added, sadly. She smiled and said, “So you’ve got a boyfriend, huh?”
“I guess, since we had sex, that probably makes him my boyfriend,” I giggled. “We were kissing and petting too, though. I just hadn’t thought about it that way. I mean, I wasn’t really looking for a boyfriend. We just had sex because of my poo problem.”
“Well, whose idea was it?” Tina laughed.
“His,” I said.
“I’m sure he had another motive in mind when he suggested it. Guys will do about anything to talk you into sex.”
“I know,” I said. “Actually, I really liked the way it felt, and not just cause it made me poop. When we were doing it, we were spooning and he had his arms around me and I felt so close to him. When he came in me, it just felt incredible. After we were done, and I had my BM, we started petting again, and he gave me a blow job. I can’t believe I’m telling you this,” I said, smiling.
“It’s OK,” she said. “Most girls like to talk about their experiences. I just want you to know that you can confide in me if you want and I will take it to the grave.”
“Thanks, I appreciate that. Actually I don’t have any one else to confide in, especially a girl.” I paused, then said, “I really liked it though. It felt so good, especially when he ejaculated into me. It felt so warm and intimate.”
“Isn’t it just the greatest feeling when he ejaculates? You can actually feel it coming up his dick before he squirts.”
“I know! It felt so cool. I’m getting hard again just thinking about it.”
“Sounds like you like having long thick things up in your bottom.”
I blushed again. “I guess I do.” I paused. “A lot of times, when I’m doing my push job and it’s part way out and big and really stretching me out, I get a boner,” I blushed.
“Mmmm,” she said. “When I give myself an enema, I use the douche nozzle instead of the rectal tip. I just love the feeling of it stretching me out as it goes in. You should try it sometime, I bet you’ll like it too. So, if you don’t mind me asking, how did you get started wearing women’s clothes?”
“Well, I’ve always liked wearing pantyhose. When I was in seventh grade my mom started buying them for me to wear them under my slacks when I got dressed up, like for church. Then when I was in ninth grade, I joined the Young Organist’s Society. We went out and gave concerts for nursing homes and places like that. The uniform for the girls was white skirts and white pumps with a red blazer. I was the only boy, and the other moms suggested to my mom that I wear white pumps too with my white slacks so I would match them. We had to go to the bridal department at Wards to get them because they were the only place that had white shoes in the middle of winter. After we bought the shoes, she got me nude sheer to the waist pantyhose to wear with them underneath my slacks, so I looked grown up and wouldn’t have underwear lines showing. She said I needed to have a ‘smooth line’. I always felt so sleek and pretty when I wore them. I loved wearing the uniform and always looked forward to the concerts so I could get dressed up. ”
“I’m sure they did. Nylons and high heels are supposed to make you sleek and pretty,” she said. “I couldn’t believe how fascinated I was when I saw you wearing nylons and flats that day in Target, trying on women’s shoes. Then when you walked ahead of me in the mall, I saw you had women’s slacks on, and you didn’t have panty lines. I knew you were either going commando or had pantyhose on. You were smooth in the front so I figured it was pantyhose, but I couldn’t believe it, I had to ask. I hope you weren’t too embarrassed.”
“Not at all,” I said. “It turned me on when you asked.”
“It turned ME on when you said yes,” she blushed. “I couldn’t believe how excited it got me, watching you sashay ahead of me. I was SO attracted to you right then.”
I realized that she probably didn’t know that I wore hose to church every Sunday. I said, coyly, “You do know I wear panty hose to church every Sunday? Whenever you’re seen me at church I’ve had hose on under my slacks.”
“Really?” she said. “Your wife is OK with that?”
“Mmmm-hmmm. I came out to her after we’d been dating a few years. Every time she buys nylons she always gets me some.”
“How long have you been doing that?”
“Since seventh grade. My mom caught me wearing her pantyhose once. After talking to the doctor about it, and he told her it was OK and something some boys need to do, she actually encouraged it. It was her idea to wear them to church the first time. She said it would make my pants fit better and slide over my legs better when I stood up and sat down, and she was right. Ever since then I always put panty hose on whenever I dress up.”
“Wow,” she said. “You’re right, I had no idea. I would never have known if I hadn’t seen you in Ayr-Way that day trying on girl shoes with hose on.”
“Well I’m glad we met like that that day. I would never have come out to you otherwise. I was really embarrassed at first when you saw me, but then I figured, ‘what the heck’. Lots of people saw me in high heels and nylons at the Young Organist concerts and nobody said a thing. The girls all treated me like one of them.”
“That’s so cool that you got to be all grown up like that,” she said. “It’s a major day in a girl’s life when she gets her first pair of heels. It’s great that you got to practice being a woman in an accepting environment. You didn’t have to be embarrassed or anything.”
“Well,” I paused, smiling, “I was a little at first. The tough part about wearing the concert uniform was hiding my erection. When I’d get dressed and put on the pantyhose I always got a huge boner. I’d have to force myself to think about something else for a while so it would go down and I could tuck it down in the hose so I could finish getting dressed. I remember the first time I performed in that uniform. I walked across the floor after they announced my name and I could feel everyone’s eyes on me and I hoped they wouldn’t laugh at a boy in high heels. It felt like I had to walk a mile to get to the organ. I was reminding myself to walk heel-to-toe like a girl, and trying to remember the first few notes of my music so I could get started. You could hear my high heels clicking across the floor as I walked and I could feel my slacks sliding over my panty hose and I got a HUGE hard on. I was so glad the blazer was buttoned so no one could see it! I could barely keep my mind on playing.”
“Wow,” she said. “I wish I could have seen you. A cute girly boy in high heels and a shimmy in his walk! And hose on! I bet you were gorgeous, you were such a girl! Did your Mom get you a bra too?”
“No, but I didn’t need one, since I don’t have anything to hold up.”
“Too bad. She could have gotten you a training bra. You don’t need to have anything to hold it up. I would have gotten you a white skirt instead of the slacks, though. What would they have done? Not let you perform? You would have looked great, showing your legs off in your pantyhose and your white heels,” she said. “Did you do anything else girly then?”
“I noticed at the first concert that everyone else had painted nails except me. After we went back to the prep room after the concert for our business meeting, the other girls took off their shoes and were lounging around in their stocking feet, so I did too. We were noticing and comparing who had reinforced toe nylons and who had sandalfoot. A couple of the other girls had painted toes and they looked so hot through their nylons. That night I went through my mom’s nail polish and found some that matched the blazer pretty close, and before the next concert, I painted my nails. The next time we had our shoes off and I saw my painted toes through my sandalfoot nylons, and the other girls complemented me, I got so aroused. I was concentrating on looking at my nylon feet during the meeting and I actually ejaculated. I had to excuse myself and go to the bathroom quickly and clean up the semen so it didn’t stain my slacks.”
“Mmmm,” Tina said, shifting around in her seat.
“Is there something the matter?” I asked.
“No, not at all,” she said, blushing. “I’m just getting so hot. I wish I could have seen the look on your face when you had your orgasm. I bet it was priceless!”
“I remember turning really red,” I said, giggling.
We turned into the K-Mart parking lot. Tina said, ”OK if we start at K-Mart? They’re having a shoe sale.”
When we got out of the car, Tina took my hand as we were walking into the store, and it really started to get me aroused. We walked right to the shoe section. It was spring, and they had all their white shoes out. I saw a pair of high heeled stiletto slide sandals, and grabbed a pair in size 9.
“Tina, look at these. Aren’t they cute?”
“They really are,” she said. “What are you waiting for? Try them on!”
I took them over to a stool and sat down. Crossing my legs, I pulled up my pantleg and unbuckled my sandals and took them off. Standing up, I stepped into the white sandals and started to walk around in them. They fit really well, and were comfortable. I walked over to the mirror and admired myself. Tina said, “Wow! Those would look so cute with your white slacks!”
“I was just thinking that,” I admitted. “I think I’m going to get them.”
I left them on and walked around in them while we looked at shoes. Tina found a pair of wood soled platform sandals. I said,” Try those on! Those would go really well with what you’ve got on.”
“Think so?” she smiled. She stepped out of her clogs, and, sitting down, strapped on the sandals. Walking around in them, she looked even hotter than she had before. I found myself really desiring her, and wondered where things would go between us. She stopped in front of the mirror and looked at them from every angle.
“You’re right,” she said. “I think I’ll get them.”
We looked at a few more pairs, and I found some low-heeled beige Rapallo slides that were great for dates with Jake – they weren’t so high that I would be taller than him. As we were putting our shoes back on to go, she said, “I love your macramé sandals. I’ve been thinking about getting a pair but don’t know how they would fit. We’re about the same size, could I wear them for a while?”
“Sure,” I said. I watched her strap them on, my dick getting harder all the time, especially when I walked over and stepped into her clogs, and we walked out of the store wearing each other’s shoes.
We went over to the mall and looked around, but didn’t find anything that suited us. Tina said, “I’m getting hungry. How about lunch at Farrell’s?”
“Sure,” I said.
We walked up to Farrell’s, and stood in line for a table. We got one that was in a corner, so we could sit close together and talk discreetly. After the waiter took our orders and our menus, Tina reached down and took my hand again, and we started stroking each other’s fingers.
“This is so neat,” I said. “I can’t believe I’m sitting here with you, all dressed up in high heels and nylons, having lunch out in public. I feel so comfortable and natural.” And I can’t believe I’m wearing your shoes, I thought. God I’m so hard.
“We’ve got to do this again soon,” she said. “I know what would help with your constipation problem! How would you like to come to my exercise class tomorrow? My doctor suggested that I take up some exercise when I was complaining that I was constipated. It would probably help you too. It’s here at the mall, and it’s a women’s group, but there is a…. kindof sissy guy in it that doesn’t want to be in the men’s group, and the other women don’t mind. Why don’t you come along? We can bring guests.”
“That would be neat, but I don’t have any exercise wear,” I said.
“That’s OK. I’ve got a leotard you can borrow. We wear leotards with sheer to the waist pantyhose instead of tights, since it’s cooler, and footie socks and tennis shoes. Do you still have your sheer to the waist pantyhose?” she asked.
“No,” I said, “I’d have to get some. I bought some K-Mart Soft Smooth and Sheer pantyhose the other day, and they’re sandalfoot, but have a reinforced panty. I’m wearing them right now,” I added, giggling.
“You need something with a sheer panty, else it would show below the leotard. We’ll stop at Osco’s after lunch and get you some.”
After lunch, we went into Osco Drug and Tina led the way to the No Nonsense Pantyhose display. She picked out two pairs of Size B Suntan Sheer To Waist and handed them to me. She looked around to make sure we were alone, then lowered her voice and said, “Do you shave your legs all the way up? You’ll need to if you don’t.”
“I haven’t,” I admitted. “I was thinking of getting some Nair and using that, so I’ll be really smooth.”
I picked up some Nair with Baby Oil, and then we checked out, and walked out to her car. As we drove back to my house, we made small talk, and when we pulled into the driveway, she parked the car and shut off the engine. Turning to me, she put her hand on my shoulder, and said, “I haven’t had this much fun in a while. I can’t wait for tomorrow.”
She pulled my face to hers and we shared a quick kiss.
After I went back in the house, I laid around for while, basking in the great time that Tina and I had, and thinking about going in the bedroom and jacking off again, when I heard a car pull up in the driveway. I looked out the window, and it was Jake. A few seconds later I heard a knock on the door. I walked through the kitchen and opened the door for him. As soon as he got in, we were in each other’s arms, kissing deeply. As we broke apart, he asked, smiling, “Are you as horny as I am?”
“Mmmm-hmmm,” I giggled, coyly.
“How come?” he asked.
“Because I haven’t had sex for a week cause Becky’s having her period and I’ve had hose and high heels on all day and I feel so sexy and you’re so cute and I’m so horny and I can’t wait any more,” I said breathlessly, grabbing him and French kissing him again. Breaking apart, we giggled, and as we spun around, we knocked the cereal box off the counter. I squatted down to pick it up, and as I stood up, he said, “Mmmm, you are wearing pantyhose again.”
“Of course,” I replied. His hand grazed my derriere, copping a feel of my smooth curves, and then he grabbed my hand and we took off at a run for the bedroom.
This time, he undressed me. Sitting down on the bed, he grabbed my feet and brought them up into his lap. He took off my sandals, then my sweater, and then undid my button and unzipped my pants. I laid down and raised my hips and he slid my slacks off of me, then started caressing my nyloned legs.
I giggled, “So am I Soft Smooth and Sheer?”
“Oh, God, yes,” he said, putting his mouth on mine and French kissing me.
“I got so turned on this morning every time I looked down and could see my pretty toes in my sandalfoot hose in my sandals.” I French kissed him back. “Oh, baby,” I moaned, “play with my feet.”
He did, running his fingers all around my toes, and then tracing the toe seam of my pantyhose, which drove me mad. He brought my feet up to his face and started sucking my toes through my nylons.
“Your feet are so pretty. You have the cutest toes. I see why you need sandalfoot hose,” hepanted. My dick was so hard it hurt. I slid my pantyhose down to my thighs, and started to play with my huge erection. He quickly undressed, and as he turned back to me, I grabbed ahold of him and pushed him over on his back. I mounted him, and reached down and laid our dicks side-by-side.
As I laid back down on him, I kissed him deeply and started to hump him. When our lips broke apart, he said, “God, I’m so turned on. I want in your sissy pussy so bad.”
“Well, come on,” I said, smiling. I rolled on to my left side and bent my right leg, assuming the Fleet enema position, and reached back and pulled my butt cheeks apart with my right hand. He opened the Vaseline and lubed himself and then me, penetrating my anus with his lubed finger, and then guided his dick to me and gently pushed. I relaxed and he entered me. I gasped in pleasure as his big hard dick dilated me. I couldn’t believe how easily he got in me this time – it felt so natural. We immediately started thrusting together and Jake said, “Talk dirty to me.”
“Mmmmm, it feels so good with you up in my boi pussy.”
“I LOVE having long thick things up in my butt.”
“God, you’re so big and my pussy ass is so stretched out.”
That pushed us both over the edge. We came together, quickly and hard.
After we rolled apart, we snuggled back together. “I can’t believe this is happening,” he said. “You are SO hot. When I was here last time, and saw you wearing hose, it made me so aroused, but I thought I better not show it because it might turn you off. Then, when you said you were constipated, I knew that was my opportunity to get in your pants, er, pantyhose…..”
I wrapped my arms around him and said, “You can get in my pantyhose anytime.”
After he left, I slid my black slacks back on and laid around the house in my hosed feet.
When Becky came home, she said, “Wow! You look really nice. Did you have fun shopping with Tina? Did you get anything?”
“I got some white high heeled slide sandals. I also got some other things I need to ask you about.”
“Well, Tina invited me to go to her exercise class with her tomorrow, if it’s OK with you. It’s a women’s class, so I’ll be with a bunch of women.”
“Okay, go on……..”
“They normally wear leotards with sheer to the waist pantyhose instead of tights, since they’re not as hot. Tina is going to loan me a leotard, and I bought some No Nonsense sheer to the waist pantyhose. I need to shave my legs all the way up since I’ll be wearing a leotard.”
“Okay,” she giggled. “I can’t wait to see you in a leotard.”
“Actually, I don’t have it. We’re getting dressed at Tina’s house before we go over there.”
To be continued................
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