I woke up on Christmas Eve to the sound of someone knocking on the door. It was after nine o'clock. I was in a guest room in my uncle's basement sleeping in a tee shirt and pair of silky black panties with a red floral print.
Next to me was another pair of panties that were stiff with my dried cum. Angela had used them the night before to give me a handjob while everyone else in the house was asleep. It was the third time in less than a week. The first time was right after she caught me trying on her underwear.
At first I felt guilty. Angela was only eighteen years old. She was still in high school. And she wasn't my aunt's step-daughter. We were cousins by marriage, although we weren't related by blood. I'd known her since she was in elementary school. Our family thought it was cute that she had a crush on my growing up, but an actual relationship would have been scandalous.
But the guilt faded quickly. It was replaced with desire. The taboo elements to our secret encounters made them more thrilling. For years I'd fantasized about a woman embracing my desire to crossdress. Angela had. And I was becoming obsessed.
I had tossed and turned the night before. After Angela left my room I couldn't stop thinking about her. The curves of her body. Her thick, black hair. Her dirty mind. Her eagerness to stimulate and please me.
Even though I had just gotten off I wanted more. Three encounters had concluded with getting jacked off three times. She had put my cock in her mouth twice, but not given a complete blow job. I'd caught a glimpse of her bush and played with her tits a bit. It had been months since I'd have actual sex and I wanted more from Angela. I knew I was being greedy, but I wanted to push things to another level. I also wanted to wear more than panties.
I'd masturbated again with her panties before falling asleep. My eyes were closed tight as I imagined her riding my dick while I wore panties and stockings.
My late night led to me sleeping in. I knew everyone else must have had breakfast already. I assumed either my mother or sister had come down to see if I was dead. I pulled on some pants over my panties and stumbled to the door. I was surprised to see Angela standing there.
"I was sent down to make sure you're still breathing," she said loudly. She flashed that wicked smile.
"Actually I volunteered," she said quietly. "I don't think anyone followed me down."
Angela stepped into the room and pushed the door within a few inches of closing.
Her incredible curves were hidden beneath a baggy red plaid flannel shirt and loose olive corduroy pants. Her thick black hair was down and she had on her black-framed glasses. Anyone who saw her like that in a coffee shop would have just mistaken her for schlubby grunge nerd. They'd have no clue how sexy she was. Her wardrobe and the fact that she went to an all-girls Catholic school were probably the only reasons she was single.
"I might have packed some extra clothes for this trip," she said playfully.
She pulled a pair of panties from her pocket. Simple white nylon briefs with little pink roses on them.
"I want you to wear these today," she said.
"And I want you to give me some pussy," I snapped quickly.
I surprised myself with the quick temper flair. Maybe it was the lack of sleep. Or just not having a cup of coffee yet. Somehow during the night I'd started feeling like she was getting everything she wanted and I was being used somehow. Like I was her plaything. It was an absurd way to feel.
"Wow," she said with surprise. "What's that about."
I took a deep breath.
"Sorry," I said. "I'm just grumpy in the mornings and didn't sleep well."
"Sounds like more than that," she responded.
"I had a sex dream. About us." I said.
It wasn't really a dream. It was a fantasy when I was wide awake. But I was trying to recover from my rash reaction. I knew I wanted more than a handjob from her. But at the same time it would be insane to drive off the only woman who had fully encouraged my fetish. I needed to be more subtle. And content with just handjobs and panty play if that was the only option.
Angela was very curious. She raised an eyebrow.
"What kind of sex dream?" she asked.
I gave her the high level overview of my fantasy from the night before. That I was in panties and she was riding my dick.
"Sounds hot," she said. "Not much detail, though."
"You want the details?" I asked.
"Sure. Of course."
"You were on top of me," I said. "With your shirt open. Like that first night in your parents' basement. When you were grinding on my cock. Your gorgeous tits bouncing."
"You like my boobs?" she interrupted. "They're not very perky."
"Fuck yes, I like them," I gushed. "They're full and sexy. I can't stop thinking about them."
"What else happened in the dream?"
"That's it. You were on top. You were riding my cock. And I was wearing white satin panties and stockings. I had to jack off after it."
"Stockings?" she said. "That's new. So it's not just panties?"
I blushed a little and nodded.
"Have you worn stockings?"
"Only briefly," I admitted.
"Whose? Mine?"
"No. One of our neighbors. Years ago."
"What else have you worn?" she asked.
I was worried that I was going to freak her out. A panty fetish is one thing. But full blown crossdressing? That could lead to a lot of suspicion about my sexuality. Still, I felt the need to be honest. I told her I'd tried on slips and other lingerie.
"Ever worn a dress?" she asked.
I told her I had. It was actually the first thing I'd ever tried on. I was spending the night at a friend's house and had impulsively tried on a dress his mom had hanging in the guest room.
"Do you want to be a woman?" she asked. "Are you bisexual?"
"No," I answered. "I just get turned on by it. The taboo. I don't know why."
In truth I had gotten a blow job from an older crossdresser just a few months earlier, but I just considered it experimentation. I didn't plan on doing it again. And I didn't plan on telling her or anyone else about it.
She seemed to think about my answers for a second.
"I wish I had some stockings for you to wear," she finally said. "I'm kinda wet."
"I'm kind of hard," I answered.
"Show me," she said.
I slid down the track pants I'd pulled on earlier. There was a growing bulge in my panties.
"Let me feel how wet you are, Angela."
She glanced at the door that was only slightly ajar.
"I've been down here awhile," she said. "What if someone comes down?"
"I'm sure they think you're just hanging out while I get dressed or whatever."
She bit her lower lip and thought about it for a second. She sat down on the edge of the bed and unbuttoned her pants. She pulled the zipper down and held them open. Her panties were simple white nylon briefs with a white bow on the waist band.
"Go ahead," she said. "You can touch."
I sat to her right on the bed. I slid a hand down her pants and cupped her pussy. I could feel the heat coming off it. Her panties were definitely damp.
She touched me at the same time. She cupped my dick and rubbed it through the panties she'd given me a week earlier. I went from semi-erect to fully hard.
I rubbed her pussy faster and she let out a soft moan.
"We have to stop," she said. "Someone is going to come downstairs."
"They've forgotten you're down here," I said. "They're probably all talking or wrapping gifts or taking a nap."
"My brother," she said. "He's using the room next door. Or he will come watch TV."
"Nobody is coming," I told her.
I was actually as nervous as she was. But I was also 21 years old and insanely horny all the time. It was worth the risk. At that point in my life even fingering a woman was still a thrill.
I slid her panties to the side to get inside her pussy. My index finger slid in easily. She gasped.
"We have to stop," she said again. "We can't."
"Can't right now? Or can't ever?" I asked.
I spoke slowly. Sliding my finger in and out of her pussy at the same time. Making her moan.
"Now," she panted. "Or maybe ever. I don't know. It seems wrong. It's too much."
"And jacking me off isn't wrong? Putting my cock in your mouth isn't wrong?"
"No," she said. "I mean yes. It is."
She whimpered as I worked another finger into that tight pussy.
"It is. But it's not as bad," she said. "It's just a little bad. This is really bad. My dad is married to your aunt. We're kind of cousins."
I kept working my hands in her pussy. I'd been fingering girls for along time. I was confident in my ability.
"But we aren't cousins," I said. "Not really. Just by marriage."
"They'd kill us," she panted. She was squirming on the bed. "They'd disown us."
"But they'd be ok with you using your panties to jack me off?"
"Yes," she moaned. "I mean no. They wouldn't."
"We've already crossed the line," I said. "I want to make you cum. And I want more than handjobs."
"Yesss," she said. "I want to cum."
"Are you a virgin?" I asked.
She shook her head.
"Then there isn't a reason to stop," I told her.
She was close. I found her clit with my thumb and touched it. She responded as if she'd been hit by lightning. She yelped and squirmed.
"Oh fuck," she moaned. "Make me cum. Please make me cum, daddy."
I kept working her clit I finger-fucked her. She moaned loudly. She bit her lip. And then Angela came for me for the first time. He through an arm around my neck and hugged me tightly. She pressed her full lips to mine and slid her tongue in my mouth.
"Nobody has ever done that for me," she said. "I've only gotten myself off?"
"But you're not a virgin?" I asked.
She shook her head again.
"Only one guy though. Only a few times."
"Who was it?" I asked.
"What's it matter," she said. "You're not going to know him. Just some guy I met."
"What happened to him?"
"It couldn't last," she said. "He was older. I couldn't bring him home to the parents. Especially not my mom. There wasn't a future."
I nodded to let her know I understood. I didn't need the details.
I kissed her again. I reached under her loose flannel shirt and felt her tit. I pulled at the cup so I could touch her hard nipple. That always felt like a real achievement at that age.
"I want you to cum, too," she said. "Where are the panties from last night?"
I knew she wanted to jack me off again.
"I don't want another handjob, Angela."
"We can't fuck," she said.
"I want a blow job," I said. "All the way."
"I've never done that," she said.
"Really?"
She nodded.
"Then that will be even more amazing."
"Someone is going to come downstairs," she said. "Just let me use my hand."
"Nobody is going to catch us," I said confidently, even though I was worried, too. "We can shut the door and lock it. If someone comes you can hide in the shower. I'll say I don't know where you are. That you woke me up and left. Maybe you're outside smoking weed."
She rolled her eyes and laughed.
"That would probably be better than what we're actually doing."
She stood up and walked to the door. She hesitated for just a second. I thought she might change her mind and leave me to take care of myself. Then she shut the door and locked it.
I came up behind her and pressed her against the wall. She'd buttoned her pants when she stood up, but I unfastened them. They started sliding down.
"I want to see this body."
"No," she protested. "I'm too jiggly," she said. "Guys don't like fat girls."
I couldn't believe she thought that way about herself. She had an amazing, voluptuous hourglass figure. She was carrying some extra weight, but it was sexy as hell. But she had always been a little overweight as a kid. And she was still in high school, where most of the girls are a size two and the boys are only interested in stick figures. Angela hadn't realized yet that she had the kind of body that would always drive some men wild. There was no Christina Hendricks on TV in the late 90s giving curvy young women confidence.
"You're not fat," I told her. "You're perfect. You make my cock hard. I want to see you."
I kept her pinned to the back of the door with my arm and worked her pants down around her ankles. I kissed the back of her neck and fondled her big tits. I dropped my own pants. The two of us stood there in our panties. Mine black and hers white. My cock was rigid. I started grinding against her ass. I thought I might cum before we got any farther.
Angela reached behind her and rubbed my rigid cock through my panties.
"You like that?" she asked. "You like when I rub your dick through your panties?"
I was dying to stick it in her. I would have only lasted a few seconds and I didn't care. I grabbed the waistband of her panties and started tugging them off her plump ass.
She slapped my arm forcefully.
"No, no," she said. "Not that."
I pulled back a little in response to the slap. She was able to break away from my grip. She put her hand on my chest and started pushing me to the bed. I took off my shirt and sat down on the edge. I wrapped an arm around Angela's waist and pulled her close. We kissed passionately. I started with the button on her shirt.
I could tell she was apprehensive, but she didn't stop me. And I didn't slow up to give her a chance to protest. Her bra was cream colored with lace over satin cups. Her stomach wasn't flat, but with was still sexy.
"Take it off," I said. "All of it."
"The panties stay on," she told me.
I nodded. She shrugged out of her shirt. Then unclasped her bra and let her big tits spill out. They were amazing. Very full tear drops with retrousse brown nipples. Her fullback bikini panties barely covered her big ass. The white was sexy on her olive skin.
She started to get on her knees.
"No," I said. "In bed."
"Why?"
"Because I want to see those perfect tits hanging down while you do it."
I laid on my back. Angela pulled my panties down just below my balls. My rigid cock stood up. She straddled my legs and leaned forward. Then she wrapped her lips around my cock.
I felt even better than previous times. Probably because I knew she wasn't going to stop. I was going to fill her pretty mouth with my cum.
I loved staring at her jiggling boobs as she went up and down my thick shaft. She couldn't take all of it, but I didn't care. She tugged on the base a bit. It was a little clumsy. I'd definitely had better. But never while wearing panties.
I became hyper aware of people moving around upstairs. Footsteps crossing the room above. The fear of someone coming down the steps is the only reason I lasted more than two minutes.
Angela didn't make eye contact or alter her rhythm very much. She did tease my cum hole with her tongue. She bobbed her head up and down faster than I would have liked. She kept squeezing and releasing the base of my dick with her hand like she was trying to milk me. I couldn't take my eyes off her swaying tits.
"I'm so close," I gasped. "I'm gonna cum."
She pulled her mouth away for a second.
"Is that what you want? Do you want to cum in my mouth?" she said in a husky voice.
"Fuck yes, Angela. I want you to swallow my cum."
She wrapped her lips around me and moved even faster. She tugged my dick. And I erupted. It caught her by surprise and I could hear her gagging. She pulled her head away quickly and cum ran out of her mouth. My cock was still spasming and I shot on her tits and my own stomach.
"Lick it up," I told her.
"Is that sexy? Is that what you want?"
"Yes."
She did as told. A little tentatively at first. But then she made a show out of it.
She came up and laid next to me. We kissed.
"You want to come shower with me?" I asked.
"You know I can't!" she said.
She got out of bed and started dressing in a hurry. The panties she'd brought down earlier were on the bedside table.
"Are you still going to wear these for me?" she asked.
"Is that what you want?"
"If it will make you horny," she said.
"You know it will," I answered.
"Then put them on. Although you probably won't need them. I have a dress that you won't be able to look away from later," she winked at me and went to the door. Then she opened it a crack and slipped out.
And I went to shower, knowing the satisfied feeling wasn't going to last for long.
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