Sunday Morning Pantyhose 34

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Sunday Morning Pantyhose XXXIII

By

Tracy Davis

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 bought me pantyhose and started encouraging me to wear them, and then it was all downhill from there. -- Tracy

Later that summer, I got a call from Jimmy, the boy I had gone to the fair with several years before. He asked me on a dinner-and-movie date. I was so flattered, but I also had so many questions. This is unchaperoned! What if he wants to make out? What if he finds out I’m really a boy? I said, “I’ll have to check with my mom. Why don’t you call me back later tonight?”
During dinner, I brought up the subject to Mom. She smiled and asked, “Are you really ready to go out by yourself as a girl?”
I said, “I think so. I’m just so nervous. What if he figures out I’m a boy?”
“Good question,” Mom replied. “You’ll just have to look as convincing as possible. And make sure he keeps his hands to himself.” After a pause, she said, “You know, it’s probably time we had a talk about what to expect on a date.”
“OK, go ahead,” I said.
“Well, you already know how to have sex with a girl. It’s going to be different when you’re the girl. As you know, girls have three holes that boys want to stick their faucet in – their vagina, their rectum, and their mouth.” She paused, and then said, “And since you don’t have a vagina, its going to be your mouth or your rectum.”

When he called back later that night, I got so excited, and had to work to keep my voice calm. We agreed to go out the following Saturday night.

When Saturday afternoon came, I got out my girl jeans and my white turtleneck top. I decided to wear my white high heeled sandals, so I put on sheer-to-the-waist pantyhose. After I got dressed, I walked into Mom’s room and put on a little of her perfume. When Jimmy rang the doorbell, I sashayed to the front door and opened it, feeling so excited! We walked into the family room, my high heels clicking on the tile floor. After he met my Mom again, we chatted for a few minutes, then Mom said, “Have fun you two. Be home by eleven.”
Jimmy said, “Of course. Nice seeing you again, Mrs. Carson.”

We had a great time at dinner and the movie. After the movie let out, I went to the ladie’s room and tinkled and refreshed my lipstick. When I came out, as we were walking to the car, he put his arm around my waist and I reciprocated. I saw him staring at my pantyhosed feet in my sandals. My faucet started to harden into an erection, and I hoped it wasn’t noticeable. After we got in his car, we just sat there and talked. I had never been out on an unchaperoned date before and wasn’t sure what to expect.
He finally broke the ice. “Brian, you are just so pretty. I’d love to go out with you again.”
We drove around for a while, and then he drove into an out-of-the-way parking lot and parked. “C’mon, let’s get in the back,” he smiled.
We got into the back, and he took me in his arms. I looked up at him, and we shared an awkward kiss. “Mmmm, that was nice,” I smiled.
We kissed again, and again, and then I felt the tip of his tongue penetrate my lips. I opened my teeth to let him in, and the feel of his tongue sliding in and out of my mouth was so sensual. The next time, I put my tongue through his lips, and he admitted me, and I explored his mouth with my tongue. Oh my God, this is heavenly. The next thing I knew, he had his hand on my breast, and was starting to squeeze.
Gulp. Oh no. Has he ever squeezed a real girl’s breast before? Does he know how it feels? Can he tell that my breasts aren’t real?
What should I tell him?
I swallowed the lump in my throat, and wondered what to do. About that time, he let go of me, shifted around in his seat, and reached down in his pants. “Sorry,” he said, “I’m getting……… really hard and its starting to hurt. Just let me straighten it out.”
“Um, sure, no problem,” I giggled. Good thing you don’t know I’m having the same problem, I just can’t fix it like you did. I decided to push his hand away if he went toward my crotch, but he didn’t. We just kissed and necked, with his hand on my breasts. Finally, we ran out of time, and he took me home. He walked me to the door and I wrapped my arms around his neck, and we shared a nice long good-night kiss.
After I got inside, Mom said, “Wow, I guess things went well on your date. Are you going out again?”
“He’d like to. I’ve got a big problem though. We were making out tonight, and we didn’t go very far, but I started to panic when I realized what would happen when he figured out that I’m not a real girl. Then what do I do?”
“That’s a good question. If he is at all homophobic, he might react negatively, and we don’t want you to get hurt. You may just want to make an excuse the next time he asks you out if you don’t want to be around him if something bad happens.”
I started to tear up. “I know. I like going out with boys, but I really feel more comfortable around girls. Like Norma. And Char. And you,” I added.
Mom came over and sat down next to me. “That’s really sweet,” she said.
“Tonight after the movie, we were in the back seat of the car, and we were kissing and making out, and I started to get really hard,” I admitted. “I was afraid he’d notice. It was really pinching in my tight jeans, but I couldn’t do anything about it.”
Mom reached up and touched my hair lightly. “Sounds like you need to relieve some tension,” she said, smiling.
I smiled back, “I bet you do too.”
“Mmmmm,” she agreed. She took my hand and I stood up, and we walked back into her bedroom. I sat down on the bed and took off my high heels, then stood up, unbuttoned my tight jeans, and wiggled them down my pantyhosed legs. Mom shrugged off her dressing coat and we fell into each other’s arms, kissing, and then collapsed on the bed I pulled my pantyhose down to my thighs and mounted her, and we made slow, passionate love.

The next month was Christmas, and Char came to visit for a week. Since the spare bedroom was in ‘my’ end of the house, I was hoping maybe we could sleep together. When she arrived, I helped her get her suitcase into the spare bedroom. She was really chatty and touchy-feely like during the month we had spent together. She opened her suitcase and took out a really sexy lacy nightie, and held it up to her. “What do you think of this? I bought it just for this trip,” she purred. “I was hoping that you could sleep in my room.”
“Mmmm, that would be heavenly,” I smiled back. She put her hands on my waist, and I reciprocated, putting my arms around her neck. We pulled each other close and our lips met. We kissed, once, twice, and the third time was French. Our tongues danced in each other’s mouths, and my faucet hardened into an erection. When we broke apart, she pushed the door shut, then took my hand and led me to the bed. We stripped off our clothes and stood there facing each other in just our bras and panties. Looking down at my groin, she said, “Ooh, pretty panties,” with my hardening erection straining against the lace. She started running her fingertips over my bra, and said, “I think this is one of the bras I got you last summer.”
“Mmmm, it is,” I cooed.
“You wear it well,” she smiled. We stepped into each other’s arms for another hug and kiss, and then I felt her hands go up to my bra clasp and unsnap it. I reached back and unsnapped hers as well, like we always did the previous summer before we had sex. We broke apart and shucked off our bras, and pulled our panties down and off. We dived onto the bed, and she spread her legs wide. She pulled me on top of her, moaning, “Oh God I need it so bad. It’s been so long.”
I entered her, and we started to thrust together when Mom tapped on the door and opened it. “Oh!” she said, surprised. “I guess you two are getting reacquainted.” She pulled the door back shut and we resumed our efforts, hardly missing a beat. We fucked hard and fast, and quickly climaxed together.
After we got done, relaxing in the post-coital glow, she asked, “So do you have a boyfriend yet?”
“No,” I admitted. “I’ve been out on a date, but I was afraid he would freak out when he discovered I was a really a boy.”
She laughed. “You know what the solution to that is? Get him so turned on that he wants to fuck so bad that he doesn’t care that you’re a boy.”
I smiled. “OK, I’ll think about it.”
She said, “The reason I asked is that I got you a present to….. help when you start dating.”
“Now I can’t wait till Christmas morning.” I giggled.
“Well, I didn’t wrap it. It’s not something that you’ll want to open up under the tree in front of Mom, probably.” We got up and put our clothes back on, then she reached in her suitcase and got out a package. She handed it to me and said, “Here you go.”
I started to open the box, and she said, “It’s a dildo. Do you know what a dildo is?”
“Um, no,” I said as I took it out of the package.
“It’s a prosthetic rubber penis. It’s like a sex toy. Women use them to masturbate, when they don’t have a man around, to make it seem like they’re having sex with a man. You can put it up in your rectum to experience what it feels like when a boy sticks his penis up into your bottom. It will also dilate your anus to allow a boy to get inside you easier. I thought it would also help with your constipation problem. It’ll help open you up so you can pass a large hard stool easier.”
“Oh wow,” I breathed, as I looked at it. It did look just like an erect penis. Even after just having sex with Char, I started to get hard again from looking at it.
“After while, we’ll get out some lube and you can try it out. Do you have any lube?”
“Yes, Mom got me some. It’s in my purse. She also got me condoms.”

Later that evening, I saw Char and Mom whispering about something. A little while later, Char came up to me and said, “Why don’t you put your nightie on and come into my room. Bring your lube with you. Did you have a BM today?”
“Yes, this morning.”
“Good. I was going to have you go sit on the toilet and try to go if you hadn’t, so you’re empty inside.”
My heart starting to beat fast. I went in my room and got ready for bed, taking off my clothes and putting my nightie on over my panties. I got my purse and went back into the spare bedroom, where Char and Mom were waiting.
Mom said, “You’re really going to experience being a woman now. Lay down on the bed in the enema position. Pull down your panties, and lay on your left side. Bend your right knee up to open up your bottom.” I did, and then she handed me the dildo.
“You need to use LOTS of lube. Put some on your finger and lube your anus really well.”
I opened my purse and got out the tube of K-Y, opened it, and squirted some on my finger. I put my finger in my crack, located my anus, and rimmed it with the lube. I could feel my pubes stirring as I started to get an erection.
“Now, put some up inside you.” I squirted some more jelly on my fingertip, and located my anus again. This time, I relaxed and pushed my finger up inside my rectum and moved it around to distribute the lube. My dick hardened into a full-on erection.
“Now, lube up the dildo.” I squeezed the tube again, and smeared a bog gob of lube onto the head of the fake penis.
“Now, put the head of it inside your crack. Just get used to feeling it in there.” I maneuvered it slowly into my crack, steering it around until the tip was resting against my anus.
“Now, just relax. Imagine your boyfriend is spooning behind you, and he’s holding you and kissing your neck.” I closed my eyes and imagined making out with Jimmy, my date from several weeks before. I wonder what he’s doing tonight, I thought.
Char’s voice brought me back out of my reverie. “Now, gently push against your anus with the tip.” I did, and felt it start to open me up. It actually felt good! “Go slow. If it starts to hurt, stop. You might try releasing the pressure and then trying again, that may help spread the lube around.” I did, and then resumed slow pressure. I wanted it in me so bad! I felt myself opening up wider and wider, and then suddenly, it popped inside me all the way, with a little pain. “Oh! I think it’s all the way in!” I gasped.
“Not really,” Mom said. “You’ve got a few inches to go.”
I resumed gently pushing, and it slid farther and farther in me. Finally, the base was resting against my anus. “There!” Char said. “Now you’re in all the way. How does it feel?”
“Wow, it’s so big. It feels like I’m really constipated.”
“I bet,” Mom laughed. “It’s like having a really big hard BM.”
I relaxed and took a breath. The discomfort was passing. I playfully clenched my anus around it, and it started to feel sexual! “Mmmm, it’s actually starting to feel good!”
Char giggled, “Judging from that great big boner you have, I would say so!”
As I released my fingertips, I felt it start to slide back out of me, then I pushed it back in. I did that several times, and then said, “Wow, is this what it feels like to have sex?”
“Mmm-hmmm,” Mom and Char answered in unison, and we all giggled. Char said, “Now, roll back onto your back and take your hand away, and it will stay inside you so you can pleasure yourself.”
I did, and my hard-on was standing straight up! I took it in my hand and started masturbating, while Mom and Char watched. It felt SO incredible!
“You have such a pretty cock,” Char said. “Here, let me help you.” She bent down over me, taking my cock in her mouth, and went down on me. I was in sexual overload! It was only seconds before I climaxed, my anus contracting against the dildo, and then I collapsed into the bed, exhausted.
After a few minutes, Mom went into the bathroom and got some tissues. When she same back, she said, “OK, now push it out slowly.” I rolled back onto my side, grabbed the base, and pulled while I bore down and pushed it out of my rectum. I looked at it after it came out, and Mom wiped it off with one of the tissues.
“You need to wipe your bottom. Do you want me to do it?”
“Yes please,” I said. She put the other tissue and her finger into my crack and wiped me, cleaning the remaining lube off my anus.

After we cleaned off the dildo, Char said, “OK, here’s some sex basics for you. If you’re going on a date that you think might lead to sex, make sure you have a BM that day. Your boyfriend isn’t going to want to run into your stool with his dick. You may want to take a laxative the night before to just to make sure you go. Before you go on the date, lube yourself up well and put the dildo in your bottom for a while. That will get you opened up, and make sure you’re lubed inside. It’ll also get you in the mood for sex. And be sure and take lube! Offer to lube up your boyfriend before you begin. It’s a great opportuning for foreplay!” After a pause, she added, “And we’re going to want to hear all the details after you get home!”

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