Men Wearing Panties, Pantyhose, And Lingerie
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Title: Jane And I
It was late winter, early 1989, when things began to heat up between Jane and I. We had known each other previously, when I took my first Accounting 1 class, and had her as my instructor. Unfortunately, the class was on a Monday, as was a weekly billiard tournament, so I missed nearly half the class, each week. I ended up with a C for that class, but I wanted to try and keep a 4.0 GPA, and so I chose to take it a second time. Imagine my surprise when I ended up with the same instructor.
Jane was an ?older? woman, about 40 to my 19, red hair, freckles, quite pretty and a wonderful personality. She was also surprised to see me back in her class, and came to ask me about it when we had our break. Always one for flirting, I told her it was because I liked her, and wanted to see her again. She laughed, and we chit-chatted, with me eventually asking her out for a drink after class. Although it was awkward when she inquired about me being under age; I pointed out that I just drank water, and that bar tenders never gave me a hard time because of it.
We had that drink, and a couple others, and I eventually ended up following her home, to make sure she got there. Once there, she got into my car, and we made out for about 30 minutes, before I sent her in to bed. A couple weeks later found us making out on her living room floor, where I pleased her orally for more than an hour, before leaving her laying there panting, to head home.
A few more ?dates?, and a couple months, found me moving in with her. Things were great. It was exciting, as most new relationships are. We found we were extremely compatible sexually. I was sized and shaped to make her cum easily, and even with my premature ejaculation, we nearly always orgasmed together.
Things went along well, and it had been about a year-and-a-half, when I was laying in bed reading Penthouse Forum, and offered her a story to read?
?So what do you think,? I asked Jane as she handed the magazine back to me.
?About what? Wearing women?s clothes??
I nodded.
She shrugged. ?It?s alright, I suppose. Never really thought about it. Why??
Sheepishly, ?I used to wear panties, before we got together.?
Her eyebrows raised up, ?Really? And where are these panties now??
?I left them at my mother?s house. They were just for fun. I never really gave them much thought.?
?But you are thinking about it now??
?Yeah.?
?So you want to start wearing panties again??
Sheepishly I nodded.
?Okay. I don?t see why not. No one can see what you?re wearing, anyway.?
Later that afternoon we went to JC Penney, and purchased 6 or 8 pair; came back to the house, and I modeled them for her.
?Boy, it sure does seem to excite you just to wear a pair of panties,? she teased, as she grabbed my hard cock. Rubbing it through the panties she added, ?I guess we?ll have to do this more often, and maybe find out what else you used to do before you moved in.?
And thus was the beginning of my regularly wearing panties.
Jane was quite comfortable with sex, and her sexuality, and didn?t have a problem discussing things; or with walking around naked; or us randomly deciding to have sex. Early on she showed me her vibrator; let me watch her masturbate; and from the beginning told me how she wanted me to lick her pussy, to best make her cum. So when she began asking me questions about my sexual past, it was easy to talk to her.
After some gentle probing, I told her about sometimes playing with a cock-sleeve my parents had; how I used to put my legs over my head, to cum on my face, and in my mouth; and about my being interested in exploring submissiveness, and some light S&M.
The entire time we were talking, we were lying in bed; me in my new panties, her in her jeans and t-shirt. She was watching and listening intently, all the while her hand was slowly stroking my hard cock.
When she ran out of questions, and I ran out of answers, she decided we needed to try something else. So she had me put my legs over my head. Once done, she pulled my panties up (down?) so my hard-on was exposed, and began to stroke my faster.
She brought her head down and kissed me, without stopping her ministrations. Then moved her head next to mine, turned to look back up at my d1ck, and asked, ?Are you enjoying this, sweety? Do you want to cum on your face??
?Mmmhmm?, was all I could muster, as her hand pushed me closer to the edge.
She sat back, watching my face as my orgasm approached. Then all of a sudden it was upon me. I came in gushes. More than her, or I, could believe. As I came, some went into my mouth; some on my chin; more across my nose and eyes, and forehead. She tenderly squeezed every drop out, before taking her finger and collecting what was on my face and lovingly offering to me to suck from her finger. Without hesitation, I sucked every drop from her offered finger, and we finished up with a lingering French kiss.
As our lips parted, she said, ?That was so sexy, Mark. I think I?m going to enjoy doing this with you, from now on.?
She helped me lay back down; pulled my panties back into place; then we laid down and took a nap together. Both of us smiling from how things had progressed.
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A couple nights later, shortly after we had crawled into bed, Jane rolled towards me, holding her vibrator. Looking into my eyes, she turned it on, and moved it down next to my soft penis. The feeling was incredible?
?How does that feel?? she asked.
?Great.?
?I thought you might like that. I see you?ve been wearing your panties every day, so I thought we might try some more of what we talked about.?
Feeling my cock standing at attention, I wasn?t going to argue with her. ?What do you have in mind??
She smiled at me, held up a bottle of mineral oil, and said, ?Turn over.?
I did as she asked, while she changed position and moved down near my midsection. She began to slowly slide the vibrator up and down the crack of my ass, teasing my anus with the tip, before slipping back down towards my perineum.
The vibrator was moved away, and I was expecting to feel her fingers spreading the mineral oil, when I jumped at the touch of her hot tongue, and breath, as she licked my anus. It was a truly wonderful feeling, and I still wish I could experience it more, but it is difficult to find someone to do that, on a truly regular basis.
I moaned as she continued her rim job. She stopped, and teased, ?Oh, so you like that, huh??
?It?s wonderful,? I replied breathlessly; placing my face back into the pillow when she put her tongue back on me.
After a minute or two, she sat back up, and I felt her dribble oil across my butt cheeks. Gently, she began using her fingers to work it into the skin, moving in slow circles, pushing ever closer to my back entrance. It felt like an eternity before her fingers began working their way around my anus, and still longer before she finally worked her first finger into me.
It had been quite some time since I last played with something in my ass, but nothing had ever prepared me for the feeling of another person tenderly sliding something into it. My sphincter clutched at her warm, wiggling finger, as she slowly slid it in and out. I could only imagine how it might look from her vantage point.
?You like that, sweety??
?Mmhmm.?
?You want me to keep going??
?Yes, please.?
?Okay. Let?s try a little more oil, and then we?ll try the toy.?
?Okay.?
I felt her pour more oil on me, but closer to my hole, before she pulled out her finger, and began spreading it again. I felt her finger come back to my hole, and then felt myself stretch as I realized she was slowly sliding 2 fingers into me. When she did this, I made a conscious effort to relax, taking a deep breath, and trying to open myself up to her. Once I did this, her fingers slipped right in, and she again began to slip them in and out of me.
After a few seconds of this she told me, ?I think you might be ready to try the vibrator. So just relax, and we?ll see how this goes.?
I simply nodded into the pillow, not even sure I could remember how to talk, as I again felt her remove her fingers; only this time there was a small feeling of emptiness, when they were gone.
I could feel her moving around, I assumed she was putting oil on the vibrator, and then I felt a cold rounded ?thing? pressing against my ass. I could feel it slowly begin to slide in, though it met resistance quickly, as it reached the limit to what her fingers had stretched me to.
I could feel her slowly twist the vibrator, while at the same time she gently pushed in to me. And I could feel a part of myself that wanted the feeling of being filled back, even though I knew this would be a lot bigger than her two fingers.
She reached down, with her free hand, and gently rubbed my cock. She ran her fingers across the top, feeling all the pre-cum, which she rubbed all across the crown, before beginning to move in long, slow strokes.
?Relax, Mark. I?m not going to hurt you. We both know you want it. See how hard you are? Just relax and let it slip into you.?
I took deep breaths, trying to do as she said, and a little more slid into me, but there was still more waiting.
For no reason that I can remember, I then tried pushing back, using my sphincter muscles, and got a big surprise when it seemed like all resistance left, and all eight inches slid right into me.
Jane continued to rub my hard on, as she talked, ?There you go. Are you alright with that??
I nodded.
?Good.?
She began to slowly stroke the vibrator, in and out. Then, taking her other hand away from my erection, she reached down and turned the vibrator on. The feeling was nothing short of exquisite. I had never felt such wonderful things moving through the inside of my body, and the way they moved through my hard on, whoa?
As she continued to stroke I began to gently push back against her. This did not go unnoticed.
?So you really like that, huh??
?Oh God yes.?
?I see. Do you think you can turn over, on to your back??
?Sure.? I could feel Jane adjusting her hands, as I rolled over, and she held the vibrator inside me.
?Great. Now lift your legs up so I can fuck you some more.?
I did as she instructed, and she began to move the vibrator, again; only now she had increased her pace, and I could feel her hand as she pushed it as far into me as she could go.
Once she had a rhythm going, she change position a little, and began to jerk me off, again. I moaned loudly, and within a minute began cumming all over my stomach. As the spasms began to subside, Jane slowed both her pumping hands, then reached over and turned off the vibrator, but leaving it buried in my well fucked ass.
Without saying a word, she guided my legs down to the bed, and then pushed them together, so as to hold the vibrator in me. She then leaned toward my head, tenderly kissing my lips as her fingers slipped through my cum. When she took her mouth and tongue away, she replaced them with a sticky finger, and said, ?Open up, sweety. You need to clean yourself up.?
I, of course, had not one ounce of energy to stand up against her, even if I had wanted to. And, again, she fed me all my cum, before kissing me one last time.
Finally, she had me move my legs, and she slipped the vibrator out of me. I don?t know if I moaned, or groaned, or what, but I know I was quite audible about not liking the feeling of emptiness that was left in me.
Jane smiled at me and said, ?Aw. Don?t worry, we?ll be doing this again, too. You?ll have plenty of chances to enjoy something in your butt. Give me a second,? she added, as she jumped up and took the toy into the master bath, and washed it off.
I watched her naked body bounce back into the room, where she placed the toy back in the nightstand, and climbed back on the bed, announcing, ?My turn!? She proceeded to sit on my face, and I proceeded to lick her super-wet pussy until she had a screaming orgasm.
Afterward, she rolled off me, then turned back to kiss me, licking around my mouth and chin. We kissed deeply, then fell asleep in each other?s arms.
Panties became a regular part of my wardrobe, and Jane was always happy to see me wearing them. She even purchased a full-length nightgown, to add to my collection of frilly things.
Over time we experimented with many different things. One evening she showed me just how much a woman can enjoy a hot tub.
We were relaxing, enjoying the tub, her hand lazily stroking me to a hard on, when she decided to confide in me how the jets could be used for a woman to masturbate. I was intrigued, and wanted to hear more?
She explained that she normally did this by herself, but she was looking forward to the opportunity of having someone help her. She turned around, asked me to use my hands to support her, as she moved her shaved pussy in front of one of the water jets.
There was a feeling of need, on her part, as she tried to get situated and I wondered just how much she was looking forward to this. After a moment of getting the right distance, she gasped, closed her eyes, and began to really enjoy herself.
Her breathing became erratic as her body writhed in pleasure, and she began moaning as the feelings increased.
It was only a couple of short minutes – faster than I could have imagined – that she began to orgasm. It was strong, and prolonged, and her body shook as the waves of pleasure passed through her. However, I quickly realized that she was at my mercy, laying away from the side, supported only by my hands and the water. So even as she came down from her first orgasm, closing her legs to keep the water from rushing against her spread vagina, I let her legs dip slightly, allowing the water jet to rush against the top of slit, pressing against her clitoris.
Her eyes flew open, as she looked at me and asked, ?What are you doing??
?Just helping you to enjoy yourself,? I replied. Smiling down at her face, still glowing from her first orgasm.
As the pleasure built again, she closed her eyes, bit her lip, and laid back taking it all in. Her body began to tremble, and she began moaning again. A little louder than before.
Her orgasm took longer than the first, and there didn?t feel like such a need to reach it, but it was spectacular, nonetheless. As her orgasm overtook her, yet again, I still held her body in place. What followed, she had said, was the most exquisite sexual experience of her life.
Basically, she had a nearly five minute orgasm. Her body was shuddering constantly, and she squealed, moaned, gasped, and made any number of other noises while I held her in the water.
Her moans were turning into squeals, which were turning into screams, and the was she was gasping, I thought she might pass out soon. So I finally pulled her into my arms, where she sat pushing my erection into my lap as she curled close and laid her head on my shoulders.
I bent to kiss her, with the passion I was feeling, only to find she only had the energy for a small peck on the lips. We sat, huddled together, for about 15 minutes, with small trembles still running through her system. About that time I pulled her to me, stood up, and carried her naked, dripping body in and placed her in bed. She smiled up at me, as I pulled the covers up, then she rolled over and went to sleep.
While we had many other hot tub adventures, none were ever as great as that first time together.
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After a while Jane and I both tired of her using her vibrator on me, and wanted something that allowed both of us to be more participative. So, one evening, we drove across town to an adult store.
We parked and went in, not really knowing what to expect. Needless to say, we were pleasantly surprised.
We spent the better part of an hour simply walking through all the isles, looking over the products, even discussing whether or not we might purchase some. There were many people who came and went. Some headed to the video booths, in back, while others were shopping for a toy of their own.
We eventually settled on a harness, and a fleshy dildo, about 7 ½?, and what appeared to be about the same size around, as the vibrator. Figuring it wouldn?t be difficult for me to transition to it.
As we were standing there, the sales girl smiling at us both as she rang up everything, another couple, and two single guys came up in line behind us. As the clerk bagged the items, she said, ?Enjoy yourselves.?
Jane, feeling extremely horny, replied, ?Oh, he will. I?m sure of it.?
Looking at me, with a knowing smile, the sales girl added, ?Ooh. Lucky you.?
I am sure I turned 16 shades of red as I took the bag, mumbled my thanks, and headed for the door. It was; however, impossible to miss the looks I got from all the others, standing in line, as I walked past them.
Back in the car, Jane apologized for embarrassing me, but explained that she just couldn?t wait to get home and try our new toy. She then leaned over, giving me a long, deep French kiss, all the while her hand was rubbing my throbbing cock.
When our kiss broke she looked at me and said, ?Now let?s get going before I die of anticipation.?
?Yes, dear,? was my response.
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