Men Wearing Panties, Pantyhose, And Lingerie
Submitted Stories
Title: My Dressing And Susan
Tim sat at his desk, not even registering the spreadsheet on his screen. He was totally intent on the tautness through his crotch, where the teddy pulled against him; and the straps pulling against his shoulders; as well as the trip hammering of his heart. He had never been bold enough to wear anything more than panties to work, and he was sure that any person who came to his cubicle would instantly know what he was wearing.
The emerald green garment, with black lace trim, was his absolute favorite. It even had detachable garters, which he had gone without, today. He so enjoyed to feeling of satin as it caressed his skin, and he could close his eyes and remember how wonderful he looked, in just the teddy, as he was getting dressed this morning.
Tim was scared to death of anyone finding out about his lingerie. The only one who knew was susan the girl that lives next door. In fact, she gave him this teddy as a birthday gift, just last year.
Susan had discovered his desire to wear panties when they were teenagers. She came home early, one day, to find Tim prancing around in her lingerie. After getting over her initial shock, and anger, she promised to keep Tim's secret, and even to help him fulfill his desires. Her only condition being that he always modeled for her.
It was a great arrangement, and eventually he ended up with more lingerie than Susan, though most of it was kept in her room. She did make him start to keep a few things in his room when he came in to her room late one night, to grab a clean pair of panties, and caught her masturbating with her vibrator.
He stood and watched her work the phallus into her body, listening to her soft moans, fascinated by it all. Up to this point, he really had no experience with a woman's body, and had never realized how beautiful it was, and how much pleasure they obviously got from sex.
As Susan reached her peak, she opened her eyes and realized Tim was watching. However, by that time, she was too far gone to stop and her body shook as the waves rippled through her body. She bit her lip, hard, to keep from being too loud, and slipped the vibrator from her body as she slowly came down from her orgasm. Once done, she turned off the toy, and quickly pulled the covers over her body, as she began scolding him for not knocking; for standing and watching; and about respecting other's privacy.
He must have apologized a hundred times, before he could get out of there. She told him, though, that he owed her and she would make him pay. This wasn't the first time one of them owed the other, so he didn't think anything of it. But later on Susan came to collect, and certainly not in a way Tim had ever suspected.
A couple of weeks, after catching Susan masturbating, she gave him a small gift-wrapped package. He opened it to find a small penis shaped item which he later learned was a dildo and a small tube of lubricant.
What am I supposed to do with this
Shrugging her shoulders, Susan said, Some guys like to use them. You know back there. I just thought you might like to try it. No one will know, and if you don t like it, it's no big deal.
Tim just stared at the box in his hands. Okay. Well, thanks, I guess.
Kissing him on the cheek. Anytime, little brother.
It took Tim a few days before he worked up the nerve to try the dildo. And it took some time, with the lube, and not knowing what he was doing, to get through that first time. But he found that he did enjoy the toy, and began using it every couple of days.
Eventually, though, he ran out of lubricant and didn't know what he could use, or where he could get more. And after a couple of days, finally worked up the nerve to ask his neighbor about getting more.
Oh. So you did enjoy my little present, she teased. Well, good. That's why I got it for you. Don't worry. I will get you some more, tomorrow.
Thanks, Suz.
No problem. And I think I might go shopping, tomorrow, as well. Would you like me to get you something
Sure.
Anything in particular
Nah. I trust you. Whatever you pick out, will be fine.
With a twinkle in her eye, she answered, Okay. I should be back before you get home from school, so you can see it then. And try it on before Mom and Dad get home.
The next day, Tim opened the front door to see Robert and Susan kissing heavily on the couch. When he entered, they sat up, and tried to circumspectly straighten their clothing, before they realized it was he.
Tim really liked Robert. He was pretty good looking, really smart, and always treated him like he would someone his own age. And he always seemed to treat Susan great, and made her happy, which also made him happy. He liked seeing Susan happy. He guessed it stemmed from her always helping to make him happy.
Hey, Robert. Hey, Susan. What's going on
Just watching TV. Hey, we were talking about going swimming, Saturday. You interested Robert asked.
Sure. Sounds great. Thanks.
Robert, hun, I need to show Tim something. It might be a few minutes, but just watch TV, and we'll be right back.
Tim had already started towards his room so he missed Susan's wink to Robert, and the conspiratorial smile they shared. Okay.
Tim went to his room, tossing his things on the bed. He turned to see Susan leaning against his doorway. She smiled, crooking a finger, and beckoning him to follow her to her room. Once inside, she quietly closed the door, and whispered, I found something very special, for you. But you need to trust me.
You know I do. Heck, you seem to know me better than I know myself, sometimes.
Good, because that's what I did this time. I'm pretty sure you want this, and I really want to see you in this. So here.
Susan pulled a wrapped item, hung on her closet door, and handed it to him. He looked at her oddly, not sure what she was handing him, but he began to take the bag off, and was surprised to find a small black dress made out of some sort of stretchy material.
He held it up in front of him, looking at it. It looked pretty nice, but he was still a little perplexed. So You bought yourself a new dress. I like it, but what does this have to do with me
That's not for me, silly. I bought it for you.
For me I don't wear dresses, he said. Then lowered his voice before continuing, I wear underwear, but not dresses.
Oh, why not You wear panties, slips, and you even have a bra that I bought for you. The dress just finishes the outfit. And I think you would look nice in it. Please try it, for me.
Uncertain, Tim stared at the dress. You don't think I would look like a dork
Have I ever thought you looked like a dork I have always told you how cute you looked, in your underwear. Just try it.
I suppose.
Great. Get out your bra, and a short black slip. I have a couple things to get together.
Susan rifled through her drawers, as I got my clothes together. I stripped down to my panties and held out the bra towards Susan, I need help with this.
She turned, and smiled, and said, Sure.
She held it for my arms to go through, before hooking it in back and smoothing out the straps. Here. Let's try these, too, she said as she reached around and began to put something in the bra cups.
What are those
Breast forms. Nothing major, but it will give you a little bit of a chest. The dress is designed for a woman, so you need to have a little up top or it won t look right.
Oh. I guess you're right.
There. Now put your slip on, then we'll get this dress on you.
As I dropped the slip over my head Susan removed the dress from the hanger then stepped over and helped me slide it over my head, and down my body. The fabric clung to me, as she smoothed it over my hips, and down my thighs. I couldn t believe how wonderful it felt to be wrapped up in the soft garment.
She stepped back, smiled, and said, You look great. Its perfect. Go look in the mirror.
I did as she said, and was pleasantly surprised to find that I agreed with her assessment, and that I did look good in the dress. I know I certainly felt good.
Well, I don't have the other stuff, to go with it, and makeup will take too long. But come on, she said, as she took my hand and pulled me to the door.
Nervous, I hesitated, What do you mean I m not going out there, like this. What if Robert sees me He'll think I'm gay, or something.
First off, he will not think you're gay. Second, Robert already knows you wear panties, and he doesn't treat you any different, now does he
You told him ! How could you I whined.
Tim. Please. Have I ever hurt you
No. But
Have I ever done anything to embarrass you
No, I answered quietly.
Then, trust me. He's cool with it. He even admires that you do. He says you are braver than he could ever be. And I think he is right. Now, come on. He s out here waiting to see you, and I know he is going to agree that you just look adorable.
Reluctantly, and totally mortified, I let Susan drag me back down to the living room.
Here he is, Rob. What do you think
Wow! Tim, you look great. I mean, that dress really looks good on you.
He s embarrassed, Susan teased.
Dude, why I think it s totally awesome.
Surprised, I finally raised my eyes from the floor, and asked, You do
Sure. I could never be brave enough to do that. You like it, and you do it. And on top of that, you look good doing it. I don t see any reason to be embarrassed.
There, squirt. You see I told you there was nothing to worry about. So why don t you sit down and watch some TV with us.
I sat in the recliner while Susan went back and sat next to Rob. I scooted around, trying to get used to the feel of sitting in a dress. I was worrying so much about getting situated that I didn t realize the dress had slid up some, until Susan spoke.
Tim, Sweety, close your legs. I can see your panties. It s not proper for a young lady to sit like that.
I blushed as I saw Rob peek up my dress before I brought my legs back together, and pulled down the front of the dress; what little I was able to.
Once situated, I began watching the movie. It was one I had never seen before, and seemed to be nothing more than a couple making out, and hinting at having sex. I did notice, however, that the woman seemed to be wearing a dress quite similar to mine, and became quite interested in watching to see how she looked, and moved, in it. I figured if I was going to wear it, I needed to get an idea of how to walk, and sit, and move around in it.
I heard a noise, from the couch, and looked over to see Rob and Susan kissing hot and heavy. Their lips were pressed together, and their hands were roaming over each other s bodies.
I watched openly as Rob s hand began to gently rub Susan s breasts, and occasionally slip down to the crotch of her jeans. I also noticed Susan s hand clearly rubbing Rob s crotch, and could see the bulge growing beneath her palm, and wondered how big he was, down there. Being older, I was sure he was bigger than I was, but wondered just how big, and would I ever be that big.
All this was running through my mind, as I concentrated on Susan s hand, and with my hand slipping in to my lap, to rub at my stiffening erection; and I failed to notice that Rob and Susan had stopped kissing, and were both watching me watch them. When it finally registered, I turned bright red, and mumbled a quick Sorry.
No need to be sorry, Tim. It s natural to be curious. Why don t you come over here, and we ll get you a better look, Susan cooed, as she stood and reached her hand out to me.
I hesitantly put my hand in hers, and let her pull me out of the chair. She guided me in front of Rob, before kneeling down, and pulling me down next to her. She ran her hand up the inside of his thigh, as Rob spread his legs more, and leaned back. When her hand reached his crotch, she gently squeezed before rubbing it some more. During all this, my eyes were intent on following Susan s hand, totally lost in what was happening.
As she rubbed him she said, Mmmm. Doesn t that look good, Tim
My mouth too dry to speak, and not really registering what she was asking, I simply nodded.
Susan reached down and took my hand, before bringing it to Rob s leg, Here. You do it. See if you like it as much as I do.
It was strange. My hand seemed to tingle as it moved along his jeans. They felt like any other pair of jeans, but there seemed to be something special about this pair, that passed through my hand, and caused my heart to begin racing.
My hand began to get warmer as it moved closer to Rob s crotch, and I wondered what would happen when they finally met.
I felt my fingertips brush across the lump in his pants, and realized I was touching his hard cock. My breath caught in my throat, at this, and as I began to rub my hand over his erection. However, Rob only seemed to relax more, and Susan took her hand away from mine, as I was able to breathe again, and I continued to rub his hardness.
Susan spoke softly in my ear, I knew you would like that. Doesn t it feel wonderful Knowing you re making him feel good.
Again, I nodded, much more aware of what we were talking about, and still unable to actually speak.
Rob moaned softly, and said breathlessly, Oh, that feels good. You can do that all day, if you like.
I smiled to myself, before looking at Susan, who returned my smile before leaning forward and kissing my forehead, putting her arm around me, and hugging me tight.
I told you, you just needed to trust me. I m not going to embarrass or hurt you. You're my friend, and now you can even be my girlfriend, she said.
I continued to watch my hand rubbing Rob s hard cock, trying to imagine how big it was, just by feel, when Susan moved next to my ear.
Whispering, she said, Why don t you undo his pants, and take it out I think you both would like that, and I would love to see you do it, too.
I realized she was right. At that moment, all I could think of was taking out his stiff prick, and play with it in my hands.
I moved closer to him, in between his legs, and brought my other hand up as I undid his belt, and jeans. I lowered the zipper, slowly, listening to the sound and understanding that we were moving things to a whole new level. Once his pants were open, I couldn t pretend that it was an accident, or I was forced, or anything else. It would be out there, between the three of us, that I wanted to see and touch his hard cock.
I hesitated before deciding to go ahead and do it. I figured this would stay between us, and this might be the only time I could get the nerve up to try something like this. I realized that I was glad that Susan had allowed all this to happen, and that she was here to give me the courage I needed to continue trying new things.
Once his zipper was all the way down, Rob hooked his thumbs in his pants, raised himself off the couch, and slid pants and underwear down. I backed up, to give him some room, and Susan reached in to help him take them off. In just a couple moments, Rob had his pants off, and was naked from the waist down. His stiff erection sticking up from a dark patch of pubic hair and his ball-sac hanging down but with the skin pulled tight around it.
I just sat there looking at him, as he laid back and closed his eyes again. It even appeared that his cock pulsed, while I sat and watched.
Susan whispered, Go ahead, sweety. Touch it.
Repeating my earlier touching, I ran my hand slowly up his bare leg. I could feel the heat of his flesh, and the soft bristling of his leg hair. I moved my hand up until my fingers brushed his erection, then turned my hand and gently closed it around his surprisingly soft member. Then I slowly began to move my hand up and down, the way I do when masturbating. I found it the most amazing sight, knowing that it was my hand that was masturbating him.
Next to me, I heard a zipper going down, and turned to find Susan slipping out of her pants.
This is so hot, she said to me, as she slipped her hand down and began playing with herself. Keep going, Tim. Make him feel good. Do whatever you want. He wants you to, and I want to watch, she added, biting her lip as a ripple of pleasure moved through her body.
Turning back to Rob, I found myself wanting to do more. So I moved in closer, staring at his member, as I slowly lowered my face towards my gently pumping hand.
As I neared his crotch, I could smell his musk, and also see a dampness spread across the head. I realized this was pre-cum, and found myself with an incredible need to taste it. So I brought my mouth closer to him, snaking my tongue out to softly run it across the top of his cock.
When my tongue touched him, Rob jumped, causing me to pull back a little thinking he didn t want me to go that far. Then, as I continued to watch my hand, Rob put his hand on my head, and gently pressed me down to his crotch. Again, I put my tongue out to lick the head, however, he continued to press my head so I moved forward slipping my mouth down over him.
I sucked him, softly, savoring the new tastes, and enjoying the feeling of his erection in my mouth. I swirled my tongue, for a few seconds, before I began moving my mouth up and down, like I had my hand.
I felt Rob s body stiffen, as my mouth moved, and I wondered how close he was to cumming. Mmmm. God, that feels wonderful, Tim. You are a great cock sucker. You re going to make me cum soon, he said, as he held my head in his hands, running his fingers through my hair.
Oh God, Tim. That looks so sexy. Suck his stiff prick. I want to see you make him cum, and feel how wonderful it is to do that for him, Susan said between breaths, as she fingered herself furiously.
Happy that they were both enjoying this so much, I sucked harder as I moved my mouth faster. Wanting to make him cum, as well. Though I wanted to taste him even more than I wanted to make him feel good.
This went on for a couple of minutes, and I could feel Rob getting closer to the edge, when I felt Susan slip her hand up my dress, and began to rub back and forth from my own erection all the way back to my a$$. As she did, she pressed my panties in to my crack, pressing hard against my backside. Then moving back to the front, and caressing my prick. The longer she did this, the more her hand lingered at my anus. Rubbing, and pushing, and I found myself pressing my body back against her hand, as she did.
Suddenly, Rob s hands gripped my hair, and held my head in place, as I felt his body stiffen and warm jets of cum filled my mouth to overflowing. I swallowed quickly, savoring the taste as much as I could, though a small trickle slipped from the corner of my mouth.
I sucked him until it seemed he was done, then sat back and looked in to his eyes.
He reached down, collecting the dribble of cum from my chin, and placing his finger at my mouth as I opened and sucked it from his finger. That was great. Thank you. I hope you enjoyed it as much as I did.
I nodded to him, before hearing Susan moaning. I turned, and Rob and I watched as she obviously brought herself to an extremely loud orgasm.
As she came down from her peak, she laid back on the floor, working to catch her breath. Wow! That was incredible. Running her hand on my leg, she looked at me and said, Tim, you looked gorgeous doing that. I hope you enjoyed yourself, because I know I want to see you do that again.
It was nice, I responded. It certainly wasn t what I expected to happen today, but I have no regrets.
Good. Why don t you sit on the couch and watch Rob make me feel good. I have one more surprise for you.
I climbed up on to the couch, being conscious of setting myself properly, and watched as Rob knelt between Susan s legs, as he lowered his mouth to her wet pussy.
She closed her eyes, as his tongue moved between her folds, and she began running her hands through his hair, as he had done do me.
Fascinated, I watched as he expertly tongued her, centering his attention on a small nub toward the top of her cleft. When he touched this, Susan stiffened, moaned, and thrashed around. I also noticed that he had slipped a couple of fingers into her, and she was rocking her body slowly against them.
They continued, for several minutes, with Susan becoming more turned on. I could see Rob now had 4 fingers pushing in to her, and she continued to move against him, speeding up as her excitement built.
Soon, she began to moan louder, and moving her hips faster. It was obvious she was getting near her peak. She continued to get louder, and hump faster, until her orgasm finally hit, and she let out a loud scream, that I was sure the neighbors could her.
Rob held his fingers deep inside her, and rapidly flicked his tongue against her clit, prolonging her orgasm. Though he began to back off as she slowly slipped down from her peak. He finally removed his fingers, and lay next to Susan as she took deep breaths, to recover.
Susan lay on the floor, smiling contentedly, before her hand began to gently find its way down to Rob s hard-on. She gripped it gently, and slowly began to stroke it.
After a few moments, she opened her eyes, and looked at me. Did you enjoy the show
It was wonderful.
Good. Now we just need to take care of this, she said as she nodded towards Rob s erection. And I know just the thing. I ll be right back.
Susan jumped up, and ran to the bedroom. While she was gone, Rob ran his hand up and down his stiff cock.
So you liked watching me please her
Yeah. I wish I had someone to have sex with. That looked like fun, I smiled down at him; watching him slowly stroke himself.
Susan returned and once again took control of things. Tim, get down on the floor, on your hands and knees.
I did as she said, wondering what she was planning.
She slipped a pillow, in front of me, Here. You can lay your head on this.
I looked up at her, and she coaxed with, Go ahead, sweety. It ll be more comfortable.
I laid my head down, realizing how odd I must look with my butt up in the air. Then was shocked as I felt my dress being lifted, exposing my pantied a$$.
What are you doing
Taking your clothes off, Susan said, as I felt my panties being lowered to my knees. Just relax and enjoys yourself.
I closed my eyes, and tried to relax, and not be too embarrassed that my backside was exposed to them both. But I was sure that Susan was planning something to make me feel good.
And that is about the time I felt her fingers, with the cool lubricant, playing with my anus. She ran her fingers around the tight opening, before slowly working one, then two, then three fingers in to me.
Wow, you have been using that dildo, haven t you
Susan! Not in front of Rob.
Oh, sweety, he is the one who suggested it to me. After I told him about you, he thought you might enjoy playing with one. As she spoke, she pulled her fingers out of me, but then I felt something else pressing against me. Besides, it was also meant to help make this easier.
I was wondering what she meant, when I felt something warm, soft, and larger than I was familiar with, begin to slip in to me. I realized that Rob was sliding his hard cock in to me, and was going to fuck me.
Oh, please, no.
Shhh. You already showed me that you like something back there, and you already gave him a blowjob. Just relax and enjoy, sweety. He won t hurt you, and I m right here. Everything's fine.
I closed my eyes, again, feeling Rob s cock slowly slipping in to me. It was amazing, and he was definitely bigger than my dildo, and the fullness was truly wonderful.
Rob held on to my hips, as he pushed against me, burying himself in my butt. I felt him press up against me, and realized he was all the way in. He stayed still, for a few moments, to let me adjust, before he began to slowly pump in and out.
It was an incredibly sexy experience feeling him hold on to me as he pumped in to my body. And I couldn t begin to describe the wonderful feelings running through me, at that point. I could never have imagined that such a thing would feel this good. While I had enjoyed many nights, playing with my dildo, nothing ever compared to this. I wondered if this is how a woman felt, and began to imagine myself as a woman, as I concentrated on the wonderful feelings Rob was causing.
After a few minutes, Rob began to move faster, and spoke to Susan, This feels great. She's a wonderful fuck.
Well, fuck her ass good and hard. You know she wants it.
With that, Rob grabbed my hips harder, and began to pound himself into me. Bottoming out with each stroke, and causing me to gasp, each time. I couldn t believe how wonderful it felt, and I hoped that this could go on forever.
Suddenly, however, I felt hands underneath me, moving my dress out of the way before Susan s warm mouth engulfed my hard-on. Gently she swirled her tongue around, a lot like I had done to Rob earlier. And I found myself being overcome by the sensations as she sucked me while Rob fucked my ass.
Oh God. I m gonna cum, if you keep doing that, I said to Susan.
Well hold on, and let me cum in you re ass first, Rob added. I m almost there.
Things continued for a few more seconds, and I was beginning to think I wouldn t make it when Rob suddenly buried himself in me, holding himself there, as I felt him shooting his hot cum deep inside me. This was more than I could take, and I exploded into Susan s expert mouth, cumming more than I ever thought was possible.
When there was no more in me, Susan slipped from beneath me, and I collapsed on the floor with Rob coming down with me. I could feel him going soft, but he seemed in no hurry to disengage himself from me.
Finally, he slipped from my butt, then he pulled my panties up and my dress down as I continued to lie there relaxing in the afterglow of what just happened.
Oh, Tim, that was so wonderful. I hope you enjoyed it as much as I thought you would. I know Rob and I certainly enjoyed it.
I smiled, and nodded, I did. I just want to lay here and enjoy it all.
Okay, but not too long. Mom and Dad will be home in an hour, and you need to clean up and change clothes.
Sighing, I got up, Yeah.
I watched as Rob and Susan began getting dressed, before I got up and headed towards my room.
Susan called out after me, Get a pad from under the sink, in the bathroom, and put it in your panties. That ll help catch anything that might dribble out.
Okay, I called back, smiling as I could already feel a little bit dribbling out.
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