Men Wearing Panties, Pantyhose, And Lingerie
Submitted Stories
Title: Quite An Adventure
Being a senior in high school can be quite challenging. Not only can it be tough academically, but it can be tough socially as well. I'm not the most popular kid at school nor am I the least popular. I'm somewhere in that calm equilibrium in the middle of the social classes that kids these days tend to rank others in. My "love" life has been somewhat lackluster as of late, but I don't worry about it too much. That all changed the second week of my Senior year. Lunch time rolled around on that day, and I sat down with my usual crew of friends to eat some grub and get reenergized for the classes ahead. Several of the girls at our table I know, but I didn't know them very well. I happened to be sitting beside one of the cutest girls that also sat at our table on that day, her name is Hope, and a conversation was soon struck up. She has the cutest body, just right. We clicked instantly, and soon began dating. So, here we are two weeks later and we are still quite and item to say the least. What happened last weekend was earth shattering and completely blew my mind to say the least. So with that being said, let me rewind the scene back to Friday, September 2nd, 2005. I, like many others in this community, wear panties. Why else would I be here in this great place? At lunch Friday, when I sat down at the table next to Hope, I dropped by 20 oz bottle of Coke and without thinking about the somewhat short length t-shirt I had on that day, reached down and stretched my arm as far as I could underneath the table to retrieve the beverage. As soon as I grasped the bottle, I soon released that I felt a slight swaft of air on my lower back and I began to be concerned that Hope caught glance of my pink Victoria's Secret Signature Cotton Bikini sticking up above my pants waist. I quickly raised back up in my seat and noticed that Hope was smiling oddly. She didn't say anything about it, and we commenced with our normal conversations and chit chat about random going ons in the world. I figured she was just smiling randomly and had not seen my panties, or at least that's what I had hoped. After school let out on Friday, she met me out at my car in the parking lot. I asked her if she still wanted to go to the game later that night, and she replied quickly "Nah, I think I'm going to go to the mall shopping tonight." I looked at her strangely andreplied," You going with your friends or something? I thought you enjoyed last week's game." She looked back and said "I did enjoy last week's game, but I'm just going to do some shopping for myself tonight. You want to get together at my place tomorrow night?" Before I could say anything she leaned in closer to me and whispered in my ear ,"My parents are on vacation. " That my friends, settled my mind right there. "Sure thing, I'll be at your house on Saturday then." She leaned back in and placed a light kiss on my cheeks and replied softly "I'll be looking forwards to it."
I sped home, not literally, but it felt like it. That night I spent the night out with the guys, watching the football game at our stadium up at the school and then hanging out at Wendy's after the game for some grub. I couldn't wait for Saturday, but I couldn't help but wonder why she didn't accompany me to the game on this night like she usually does. I was still trying to unravel why she wanted to do some shopping, but she's a woman, and that's her perrogative if she wishes to do so. Saturday arrived quick enough and my cell phone rang around 1:30 PM in the afternoon. It was Hope, letting me know that she was ready for me to come over, if I was ready. I was in the middle of picking up some CDs with my bud Kevin, and was going to get some lunch with him after that, so I told her I'd be there around 3 PM. My heart was pounding as I pulled up to her house later that afternoon. She was right, her parent's cars were gone, and only her Camaro was sitting in the drive-way. She met me at the door and grasped my hand lightly and led me inside her humble abode. I had made sure to wear some boxers for this day, as I wasn't comfortable to tell her about my panty wearing just yet. We snuggled for a bit and watched a movie, and after the movie had concluded, she arose from the couch in her living room and motioned me back to her bedroom. With bhated breath I followed her every move, just as excited, if not more so, than she must have been. I turned the corner to enter her room and noticed a Victoria's Secret bag on the bed, plus some bags from JC Penny. Must have been the stuff she had bought last night, I thought to myself. She approached me and passes by me very closely, and I got a whiff of her sweet smelling perfume that she was wearing. She closed and latched her bedroom door and returned to face me. We got closer together and shared a long and passionate kiss. Mid-way during the kiss, I felt her hands lower and begin to unbuckle my belt. She lowered my pants and stepped back quickly. She let out a cute little sigh and said "Aww, I must have been seeing things the other day at lunch." My face quickly turned into a shocked look and I replied "W-what did you think you saw at lunch?" She lowered her head and looked at the ground and said softly "Nothing, I'm so stupid, I thought you were wearing women's panties, but I guess I was wrong.." I grinned a bit and replied, surprisingly without hesitation, "I WAS wearing panties Friday, Hope. I wore boxers today because I thought it would freak you out if I had worn my panties over here." She looked up and a huge smile had begun to spread across her face. "Well, then my shopping efforts weren't in vain," she replied. She walked over to the bags on her bed and and reached into the VS bag and pulled out a Victoria's Secret P!NK Ligh Blue Boyshort Panty and handed it to me. "Change into these," she said. Without a moments notice I was out of my boxers and directly into those snug and wonderful boyshorts. I took my shirt off and she proceeded to pull out a small bra from the JC Penny bag. She told me turn around and she placed the bra on my chest and latched it for me, and then put in some old breast forms of hers, filling out my "breasts" perfectly. I asked her if that was all, and she shook her head in a 'no' manner and dug deeper into the big JC Penny bag. She pulled out the cutest white satin nightgown with small butterflies all over it and gently handed it to me. I positioned the nightgown right and held it above me head, slowly letting the satin slip down across my shoulders and hang lightly and freely. I felt like I was in heaven.
There I stood, totally decked out in women's sleep apparel and it felt heavenly. I took a few steps towards Hope and the silk nightie swished across my legs ever so lightly, instantly giving me an erection, as if the boyshorts and bra hadn't already. She lowered her hands to the waist of her tight jeans and unfastened her belt, before sliding her pants down her smooth shaven legs. Following this she crossed her arms, grabbing the bottom of her t-shirt in each palm, and lifted in a very feminine like manner, pulling the shirt up and over head. This left her standing before me in a beautiful purple Satin String Thong and a matching bra, showcasing her perfect B cups quite well.
She turned and bent over, opening her bottom drawer of her dresser to search for something. This gave me an amazing view of her perfect ass and sexy legs as she was leaned forwards. I let my hands slide along the silk nightie that I was wearing, enjoying every bit of this moment. She raised up ever so slowly, a pink silk nightie almost exactly like mine, in her hands. She pulled the nightie over her head and turned to face me.
I couldn't keep my eyes off of her. She was simply stunning. Hell, I couldn't keep my hands off of myself, the silk material was so sensual. She pulled me in close to her and we shared a long, passionate kiss. The feeling of my "breasts" pushing into hers as we emraced, the silk that we both had on making us feel more and more excited, this experience was like a dream come true. We remained in this close emrace for what seemed like an eternity, and the way everything felt at this exact moment, I didn't want it to end.
She slowly pulled away from me, slightly nibbling my bottom lip as we parted from the kiss and embrace. She looked directly into my blue eyes and said "Let's have a little more fun, shall we?" I instinctively replied with an enthusiastic "Okay!" and sat on her fluffy bed when she motioned for me to do so. I scooted back further onto her bad, making myself comfortable. Her silk type sheets sliding over my exposed legs and arms felt great. Hope placed both of her hands on the end of the matress, and began to seductively crawl towards me.
Her body maneuvered over mine, and then she leaned down and placed another delicate and emotional kiss upon my welcoming lips. She raised up, running her soft fingers and hands over my silk covered chest all the while. She looked deep into my eyes, as if searching deep within my very own soul and said "Want to try something?" At this point in the night, I was game for anything. After giving her permission, she began to lean over to the left, reaching her right arm out towards her bedside stand drawer. She opened the drawer slolwy and reached inside and to the back of the drawer. She pulled out a small jar of lubricant and my mind bean to wonder insanely about what she possibly had planned. I would soon find out.
She made another reach into the drawer and pulled out a flesh colored 8 inch dildo attached to a strap-on like harness. My eyes widened as I realized what was about to go down in her humble, innocent abode. I instantly spoke up, slightly stumbling over my own words, "W-what is that for?" She looked up at me and replied calmly, "You said we could try something new." I was still a little wary about having someone put something in my bottom, as I was not gay and had never had any indication or desire to have anal sex. "W-well.. W-will you be careful?" I said willfully, yet scared at the same time. She smiled her warm and welcoming smile that I've come to love over the past few weeks and replied,"Of course. I would never want to hurt you. I simply wanted to see what it feels like to be on the giving end of the sexual spectrum for once." I love Hope to death, and I wasn't about to ruin this moment by backing out now, so I got myself comfortable, and she began to get ready.
She reached her hands underneath my nightie and grabbed the waistband of my blue boyshorts and I raised my hips off of the bed slightly, allowing her to slide the panties off and away from my body. She suddenly changed her tone of voice out of nowhere and instructed me rather loudly to "Turn Over!" I did so, positioning myself on all fours in somewhat of a "doggy style" position, if you will. She strapped the strap-on harness around her waist with the dildo attached to the front of it and tightened it around her delicate waist. She dipped her hands in the lubricant jar and lubed up the end of the dildo heavily, to insure that no problems were to be ran into during this sexual act. She changed her voice tone back to the Hope I know and love and, as she scooted towards my bottom on her knees, she asked me, lovingly, "Are you ready honey?" I shook my head yes, and took a final swallow, preparing myself for whatever was about to occur.
She scooted forwards a bit more, and suddenly I felt something rather large and wet press up against my anus. A chill shot up my back, the silk nightie I was wearing at the time causing the chill sensation to magnify. She placed her soft hands on my hips and begins to push inwards. I could feel the dildo slowly sliding into me and filling me up. She kept going slowly until she fit the entire thing inside of me. I let out a short sigh of relief, knowing that the entire thing was in me now. She asked me softly,"Okay, you sure you're ready for this right?" I calmly shook my head in a 'yes' fashion, and with that, she was off to the races. She began to thrust in and out of me with the strap-on, increasing her rate of speed after every pullout and re-entry. I gripped the silk bedsheets as she sped up, surprisingly feeling immense pleasure from this anal intercourse. As she reaches her peak of speed that she could do, I could feel my member throbbing intensely. A shockwave roared throughout my body and I shot my load all over her bed sheets, and collapsed face down on her bed.
She slowly removed the dildo from my anus and removed the strap on, setting it down beside the bed on the floor. She scooted up beside me on the bed and wrapped her arms around me, embracing me tightly as I caught my breath. I sat up and pulled the boyshorts back up around my waist and fixed them in place on me, and laid back down alongside Hope. We fell asleep, holding each other in our silk nighties, exhausted after a long day of adventures.
The next morning when we woke up, I changed back into my street clothes, but kept the VS Boyshorts on, as well as the bra she had purchased for me. She put the nightie in my hands, neatly folded up, and told me that it was mine as well. We shared one last kiss and a "I Love You", and I got in my car. She ran out to the driver's side window and asked me quickly before I departed," Want to get together again next weekend?" I smiled and said "Definitely." She smiled back, and I drove home, the snug boyshorts and the matching bra a reminder of the incredible night I had spent with my significant other.
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