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By the time I was 18 I was a horny young man with a more-than-passing attraction to ladies undergarments. My mom was a big fan of hanging wash on the clothesline to dry, especially delicates like lingerie. I found myself becoming aroused when she hung out her underwear, some of which was rather sexy. I loved seeing lacy bras and pretty panties swaying in the breeze. And there were a few other items that appeared on rare occasions like garter belts and babydolls that I couldn't take my eyes off of.
It's just been my mom and I since my parents split up a few years ago. She's a nurse and works all hours at the local hospital. I have a lot of time alone at home and often snitch some of her bras and panties when she's at work. Holding up her dainties in a mirror I try to imagine what she would wear on a date. She was a decent looking woman in her mid 50s and would not have much trouble getting a date. But she worked fulltime and never seemed to go out. Perhaps a doctor was fucking her in a broom closet at the hospital?
From fantasizing about my mom's lingerie I progressed to taking them to my room and rubbing my cock all over them and jacking off. Of course I take care not to get cum on the garments. Sometimes I put on a pair of my mom's panties and then put on one of her bras and stuff it with more panties! How I love twirling in front of a mirror imaging that I am a pretty girl!
Naturally my fantasies tend toward pleasing men when I'm wearing my mom's lingerie. I often imagined a well built older man pushing his big cock into my mouth and holding my head firmly. I would gag and cum at the same time. But when I'm not dressed up like a sissy faggot I am interested in girls. I love big boobs, and especially older women. Some of my friend's moms give me a hard-on whenever I see them. They're often the subject of my fantasies when I jack off.
In the last semester of my senior year I joined the photography club. I had always been interested in photography and wanted to learn more. My only camera was my mobile phone but it took pretty good pictures.
At the club I met a guy my age who used a film camera and nearly always used black and white film. He would develop and print his photos himself. We had a lot in common and became friends.
Lex and I were similar in some ways. Physically we were both slight but fit. I had been on the school swim team for years and was used to working out a lot in addition to swimming practice. Lex was into cycling in the summer and skiing in the winter.
One day the club announced a photo challenge called, "Dissonance". The idea was to take photos featuring subjects or actions that don't normally go together. The club would vote on the best photo from each member and these would be hung in the main hallway of school for the student body to vote on. The prize for the best photo was a new Nikon camera.
I'd love to win that camera but I was at a loss for 'dissonate' things to photograph. I would lay in bed at night trying to come up with ideas but they all seemed stupid.
Then Lex invited me over to his house the following Saturday to do something together for the contest. I rode to the other side of town on my bicycle and knocked on Lex's front door. It was a nice big ranch style house in an upscale neighborhood. More upscale than mine anyway.
"Hi," Lex said when he opened the door. "Put your bike around back and come in the back door."
I leaned my bike against the back shed. Lex was waiting for me at the door. "C'mon in!"
Lex explained that no one else was home. His dad was golfing, his mom was out shopping with friends and his older sister was away at college.
"I was thinking we could do something for the contest with a bunch of costumes I found in the attic," Lex said.
"What kind of costumes?"
"Mostly Halloween costumes but there's some my mom made for my sister for plays. She was in the drama club for years."
We went up to the attic to check out the costumes. There were a lot. They were all hanging on a rod and covered with drycleaning bags. "My mom is a good seamstress and put a lot of work into these costumes. I guess she hopes they will get used again."
We sifted through the costumes, The Grim Reaper, Santa Claus, a giant bunny were some that we considered using. I was getting aroused being in Lex's attic because I often jerked off in the attic of my house looking at porn on my phone. I felt secure up there knowing my mom wouldn't burst in on me if she came home unexpectedly. I associated the smell of wood and tarpaper with naughty secret pleasure. It turned me on. But I didn't want to get a hard-on in front of Lex so I tried to focus on the costumes.
We pulled out a costume that looked like Dorothy from the Wizard of Oz. It was very well made complete with a voluminous crinoline that made the dress puff out. I started imaging how the crinoline would feel against my skin.
Lex interrupted my train of thought when he held up a plastic Jack O'Lantern. "How about this Dana - you put on the Dorothy dress. I'll get you a wig and makeup and I'll do a portrait of you holding the Jack O'Lantern. With the right lighting and in B&W it would look pretty freaky."
"That might be 'dissonate' enough for the contest," I replied.
"OK let's take this stuff to the basement, my 'studio' and we'll give it a try."
Lex bundled up the dress and pumpkin. He pulled a girlish blond wig from a chest and we went to his basement studio which was just the family rec room with pieces of cardboard taped over the two small windows. It felt very private.
I sat on the couch and unpacked the dress while Lex went to find some makeup. I was getting very tingly handling the cool sheer fabric of the crinoline. I suddenly realized I was about to get 'dressed up' in front of another guy. The thought at once excited me and terrified me. What if Lex got the wrong idea. What if he saw that I was aroused? Would he think I was gay?
In a few minutes Lex returned with two cans of Coke and a basket of items. "I found all this in my sister's room," Lex said offering me the basket.
The basket contained numerous pairs of panties and a white lacy bra.
"Um, I don't think I need to wear your sister's underwear just to put on the costume."
"But you need some boobs to fill out the dress and a bra is the only sensible way to do that. I brought the extra panties to stuff the bra."
"OK, I guess that makes sense."
"Well, what are you waiting for?" Lex said as he handed me one of the Cokes. "Time to dress up."
I cracked open the Coke and took a big swig. "OK," I said then stood up. I took off my shirt, pants and socks while Lex watched me silently.
I had my back turned to Lex because I had a boner that wouldn't go away. The more I thought about it the harder it seemed to get.
"You may as well get into the part and take off your underwear and put on a pair of panties." Lex held up a pair of white panties. I looked over my shoulder. They were very pretty and sheer. I loved them. My hard-on would never go away!
"Oh turn around for Christ's sake. I know you're hiding a stiffy. It's no big deal."
God, I thought. Now I'm expected to show my erect cock to a guy? I mean, I'd die if I had a hard-on in the locker room but this was different I guess.
Slowly I turned around. Lex looked at my cock tenting my undies. "Well take them off," he said or rather commanded.
I slipped my fingers into the waistband of my underwear and began to pull them down 'casually'. I didn't want to appear nervous but I didn't want Lex to think I was doing a strip tease either.
I fished my cock out then pulled the underwear down. I stood naked in front of Lex.
"Here," Lex said holding out the panties. I took the panties and bent down to put them on. I pulled them up and tucked my stiffy in the front. My dick was poking out of the panties pointing directly at Lex.
"That wasn't so bad now was it? OK, now put on the bra." Then Lex winked and asked, "do you need help?"
I suddenly realized that I allowed myself to get into a ridiculous situation that I didn't want. "I can put it on myself, thanks."
I put the bra band around my waist and attached it in front. Then I turned it around and pulled it up putting my arms through the shoulder straps. I wriggled the bra around for a good fit.
"I don't think that's the first time you've put on a bra, Dana. Am I right?"
I muttered something. I was embarrassed and pissed off.
Lex approached me and put a hand on my shoulder. "Dana, it's ok. If it makes you feel better I dress up in my sister's panties and bras once in a while. It's weird but harmless. When I saw your hard-on I knew you were into lingerie too."
I exhaled a sigh of relief. "You're right Lex. I do wear my mom's panties from time to time when I jack off. I don't feel bad about it but so far you're the only one who knows. I've never shared a secret like this before."
"It's good to clear the air," Lex replied.
"OK now, let's pick up where we left off. Next is stuffing your bra cups with panties." Lex offered the basket to me. I picked several panties at random and stuffed them in one bra cup and then the other. I plumped up my boobies. They didn't look too bad.
Standing in front of my friend in a bra and panties made me tremble and my cock was so hard I thought it might burst.
Lex held up the crinoline. But instead of passing it to me he reached out and made the sheer fabric slide along the bump in my panties. I held my breath - it felt so good, so sexy.
"How does that feel, Dana?"
"Um, pretty good."
Lex began to slide the crinoline along my bulge again. And then an extraordinary thing happened. I grabbed the arm of the couch to steady myself as a wave of pleasure swept over me and I shot a big load of cum into my panties.
I collapsed into the couch, panting. A big cum stain was spreading across the front of his sister's panties.
Lex stood there holding the crinoline. Finally he said, "boy I wasn't expecting that!"
"I didn't expect it either! But it sure felt good!"
Lex dropped the crinoline on the floor. He unbuckled his belt and undid his pants. He knelt beside me on the couch. "This is so hot Dana. Would you suck me off? I need to cum in the worst way."
I had only sucked one cock before, a guy in the class above me. But he was kind of mean to me and didn't want to hang with me after I did the deed. I didn't want that to happen again.
Lex took his cock out of his underwear. It was on the small side and circumcised like mine. He was very hard! He moved his cock closer to my mouth. "Please," he pleaded. At least he was polite about asking for a blowjob.
Silently, I moved my head closer to his cock and inhaled the aroma. With one hand around the shaft and the other under his balls, I pulled Lex toward me until the tip of his cock was between my lips. I licked his cute pink cockhead. Lex exhaled and gently pushed himself toward me. His cock entered my mouth and I started sucking while he gently thrust his hips.
Then Lex paused and said, "why don't you put on the crinoline, I think it would look sexy on you."
"Sure, if that's what you want." I reached down for the garment then stood up to slide it up my legs. I pulled it up over the big wet spot on the front of my panties.
When the crinoline was in place around my waist I did a little twirl for Lex then nudged him to sit on the couch. I got down on my knees. Instinctively Lex spread his legs and I got into position between them. He put his hands on my shoulders and slipped a finger under each bra strap and gently pulled me toward him.
I reached out and took his cock in my hands. It was very hard. Like me Lex was blond and didn't have a big bush of pubic hair. He was rather smooth which was attractive. And his cock wasn't that big. It would be easy to suck. I stroked his cock and put one hand under his balls. Then I leaned forward and took him into my mouth. Lex moaned and ran his fingers through my hair.
I swirled my tongue around his knob and enjoyed the sweet taste of precum. He had so much precum that it lubricated his cock even in my wet mouth. I let his shaft slide deep into my mouth and started bobbing my head while keeping my tongue in good contact with his cockhead.
I could feel Lex relax as I started sucking him with a steady rhythm. Lex wriggled and shifted on the couch. I knew he wouldn't last long. I slowed down a bit to help him last longer but he pushed my head hard onto his cock so I started sucking hard and bobbing up and down faster.
In a couple of minutes Lex shoved hard against my head and spurted pulse after pulse of cum into my mouth. I kept sucking until his orgasm was over then we both rested with his cock still in my mouth. I felt a sense of satisfaction giving my friend pleasure and knowing that we shared uncontrollable sissy urges.
"That was fantastic Dana," Lex finally said. I lifted my head and got up off my knees. Lex took my hand and pulled me to the couch beside him. I plopped myself down and he moved his head to kiss my cummy mouth. Our tongues mingled and we both enjoyed the taste of his semen.
Lex broke the kiss, "When you went along with wearing panties I knew you were a sissy and I hoped we would have some fun - and we did! But I have to ask you if you ever sucked a cock before?"
"No," I lied.
"I'm surprised. You're very good at it."
"Beginner's luck I guess," I replied.
"Have you ever sucked a cock before, Lex?"
"No, I never have. But I'd suck you if you hadn't just cum." I'd learn later that he was lying too. Neither of us could admit that we had been seduced by the same older guy.
"I think I've had enough of the photoshoot, Dana. Let's go to the bathroom and get you cleaned up."
We went to the bathroom and Lex pulled off the crinoline and then the panties and threw them on the floor. Then he ran the warm water and used a facecloth to wipe the cum off my cock and balls. "I'll have to wash the panties in the sink I guess," Lex said.
We went back to the rec room and I got into my regular clothes. We didn't talk much. I could still taste Lex's cum in my mouth. We were both thinking about what just happened and hoping it would happen again soon!
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