Bella was wearing a black and white checkered wrap dress.  The deep-v neckline teased her ample cleavage. Without seeing it, I knew she was also wearing a half-slip and lingerie chosen to please me.  I pinned her to the foyer wall as soon as we entered her house. We kissed. I grabbed her soft ass.

She had a midwestern look with fair skin, dirty blond hair, and blue eyes.  She was fit, but not slender, with a big sexy ass, smooth thighs, and nice bell-shaped tits.  

I took her hand and led her to the bedroom.  I bent her over the edge of the bed and flipped her dress up.  Just as expected, she had on a cream-colored lacy half slip and a virginal white lace thong.  Her pussy was already soaked. I teased her with my fingertips until she begged for my cock. Then I held her hips and fucked her.

I pulled her hair and spanked her ass.  Each stroke was deep and hard. She moaned my name and begged for me to make her cum. I didn’t let her down.  

“Get on your knees,” I told her after her orgasm.

I twisted my hand in her chin-length hair.  Her big blue eyes were locked on mine. I put my cock between her lips.

“Do you like the way your pussy tastes on me?”

She nodded.

“Do you want me to cum in your mouth?”

She nodded again.

I fucked her mouth nice and slow.  She kept her eyes on mine the whole time.  And she took every inch of my cock. I groaned loudly as I brought myself to orgasm.  And then I filled her mouth.

It was just a warm-up.  I knew we’d have at least two more times before bed and then again in the morning.  Bella was eager to please and loved the attention. She was recently divorced from her high school sweetheart.  I was the second guy she’d ever slept with and the first one to pay attention to her needs. Her husband hadn’t gone down on her in over a decade.  He only fucked her in the missionary position a couple of times a month.  

She knew she was unsatisfied with him outside of the bedroom, but she didn’t realize how unhappy she was with her sex life until a friend had told her about the “50 Shades” books. It wasn’t exactly her cup of tea, but it made her crave something other than her vanilla marriage.  

We met on Tinder before the ink was even dry on her divorce.  She didn’t even have photographs of her face. But it was the blurb about being feeling unfulfilled in life that caught my attention.  It was shockingly honest. I suspected she’d respond to a firm, but kind man.

She was shy in bed at first, but she’d quickly come out of her shell.  The sex was the best part of the relationship. She was so inexperienced and had spent so much of her life unsatisfied that she was open to almost anything I suggested.  She just wanted the complete opposite experience that she had with her ex-husband.  

Despite her willingness to explore, I thought asking to wear her lingerie might be a bridge too far.  Even before we met, her preference was for classy and expensive underwear purchased at nicer stores. It made her feel sexy and confident even when her husband neglected her.

Bella expanded her collection when she realized how much I appreciated her taste.  She went beyond simple matching bra and panty and slips. She added garter belts and stockings and teddies and nighties  Almost everything was tasteful satin, silk, or lace. It kept our sex life lively and intense. 

I worked from home most days, and it got to the point where Bella would encourage me to relax at her place if I spent the night on a weekday.  She liked the idea of coming home from work and me being there already. As soon as she left I usually tried on her clothes. It didn’t matter that I had my own secret collection at my house.  There was a thrill in wearing her things in her house while she wasn’t there.

It didn’t matter that we had sex most mornings before she left. An hour later I’d be right back in her bed wearing her panties and stroking my hard cock. I’d spend all day in a gown or silk robe and lingerie.  Part of the thrill was the risk of being caught, which was always a fantasy for me but had only happened once way back in college.  

I wasn’t in love with Bella, so if she caught me it wouldn’t be tragic or even that humiliating.  Sure, the sex was great and I definitely like her, but great sex isn’t hard to find if you’re dating women in their thirties.  

I started taking more risks to increase the thrill.  I’d take midday naps in her bedroom fully dressed. A couple of times I invited a sissy friend over for afternoon sex in her bed.  Getting caught was inevitable.  

I was lying in Bella’s bed when it happened.  I was wearing white stocking with a garter belt and bikini panties and a white camisole  I was watching girl-on-girl porn and edging myself, so I missed the text message saying she would be home early.  She caught me red-handed.

When I walked into the bedroom I froze like a deer in the headlights.  Her reaction was a mix of horror, anger, and hurt. She cried and yelled.  Mostly she was just confused. I jumped out of bed and covered up with the white silk robe I’d been wearing all day.

Bella stormed out of the room.  I followed her to the living room.

“You know I’m just kinky,” I explained calmly.  I tried to make it seem as normal as possible. “This is just something else I like. It’s not a big deal.”

“How long has this been going on?” she demanded.

I told her honestly that I’d been dressing my entire adult life and owned my own lingerie.  But sometimes I couldn’t resist trying on hers when I was alone.

“Are you gay?” she asked.

I assured her that I wasn’t.  

“I’ve had a few encounters with other crossdressers,” I admitted.  There was no need to tell her it was a regular thing. “It’s only people who are feminine. I don’t want to be a woman.  I’ve never had an interest in men who don’t dress up. I’ve never been a bottom. I just like to have company sometimes when I dress up, and women have not often been accepting.”

She calmed down the more I talked.  I realized it was absurd that we were having the conversation while I wore her dressing gown, lingerie, and stockings.

“You said that women aren’t often accepting,” she said.  “So some have been?”

“It’s not common,’ I answered, “but a few have been.  I’ve had a few girlfriends who thought wearing panties just during sex was hot.  They didn’t know I do it alone. I had a longterm relationship with someone in college who was completely OK with me dressing up regularly.  I’ve met a few people on dating sites who were into it for no strings sex.”

She seemed to think about it for a minute.

“It seems strange,” she said. “Is it something you want me to be into?”

“I would like it very much if you were,” I said.  “You’ve been very open to exploration. This would just be more.”

“I’ve been open to being dominated,” she answered.  “I’ve liked being spanked and tied up and told what to do.  I like that you’re an alpha male when my ex was not at all. I’m not interested in a sissy.”

“I’m still an alpha male,” I told her.  “Just one who has some kinks.”

We talked some more and she told me she needed to think about things.  She asked me to put on my own clothes and leave. I probably should have been ashamed.  Instead, I went home and got off to the fantasy of wearing her clothes while we fucked.

She texted me the next day.

“I got involved with you to be open-minded and explore new things.  You’ve been respectful of my boundaries. You’ve been patient. You’ve taught me things that I love.  I trust you. Come over on Friday.”

I couldn’t wait for the week to end.  I was confident that things would go well.  When I arrived, Bella answered the door in the same white silk robe that I’d worn on my last visit.  She greeted me with a soft kiss on the cheek.

“I picked out some things for you,” she said.  “I know you’re normally in charge so you don’t have to wear them. But I thought they might be sexy.”

She took my hand and led me to the bedroom.  She’d laid out her outfit for me on the bed. It was all new things.  

“I’ll leave you to get dressed,” she said.

I quickly stripped.  The first thing I put on was the hot pink nylon string bikini panties.  They fit perfectly and hugged my quickly growing cock. Next was a light pink bra.  I usually preferred camisoles since I don’t actually have breasts, but I knew it would look sexy under the sheer white robe she’d left for me.  Last was white thigh-high hold-ups with lace trim.  

I walked back to the living room.  Bella had already seen me in her lingerie, so I wasn’t nervous.  She was sitting on the sofa waiting. She stood and looked me up and down.

“Do you like what I picked out?” she asked.

“I do.  Do you like it though?”

She looked again and slowly circled me.  Her eyes were drawn to the bulge in my panties. The outline of my cock was evident through the thin material.  

“It’s sexy,” she admitted. “Especially the way your cock looks.”

She opened the sash on her robe. She was dressed in the exact same outfit I had been wearing earlier.  Bella had on the same camisole and white panties with a garter belt and stockings. The only difference was she also wore heels.

“Is this sexy?” she asked.  “Is this how you imagined it?”

“Not that exact outfit,” I said.  “But both of us in lingerie.”

“I thought if this is what you like to wear then you’d find me sexy in the same outfit.”

“You’re very sexy,” I said.  “You’re always very sexy.”

We kissed one another softly.  She opened my sheer robe and ran her fingers over my panty-clad cock.  My entire body trembled.

She took my hand and led me to the bedroom.  She turned down the covers. We both shed our robes.  We stood in front of one another and kissed. She rubbed my cock through my panties.  I cupped and rubbed her tits through her camisole.  

“Turn on the porn you were watching,” she said.

I turned on a girl-on-girl video and streamed it to her television.  The two of us laid to one another in her bed. We kissed softly. We touched one another through our lingerie.  Bella was capable of being bold in bed, but it was usually after surrendering entirely to me for the first fuck of the night.

My lingerie seemed to change the dynamic.  She gripped my cock and teased it.

“You’re so hard,” she said.  “You feel harder than normal.”

I could only moan in response.  It had been a long time since I’d worn panties around a woman.  I was rigid. I felt like I might cum at any second. The women on the television were tribbing.

“Is that what you want to do?” Bella asked.

She didn’t wait for an answer.  Bella pushed me on to my back and straddled me.  She rubbed her panties against mine. I could feel the heat of her pussy as she was grinding on my cock.  She kissed me hungrily.

“This is so dirty,” she did.  “I’m so wet.”

“I’m going to cum,” I moaned.

“I want you to,” she said.  “Cum right in your panties.

She moved harder and faster on my cock.  She rocked her pussy up and down my shaft.  

“I love rubbing our panties together,” she said.  “We are being so bad. You’re going to cum in my panties.”

I grabbed her hips and pushed upward.  I need to cum. I didn’t last much longer.  I shuddered and came in the hot pink panties.

Bella stayed on top and rubbed her clit rapidly until she had an orgasm. Then she kissed me and got out of bed.

“Looks like you need to change,” she said.  

The pink panties were soaked from my load.  

“Help yourself,” she said, with a nod to her dresser.  “You obviously know where everything is.”

“I’d rather you pick again,” I said.

She rummaged in her drawers for a few seconds.  She tossed me a shiny pink nightshirt.

“You always fuck me really hard when I sleep in this,” she said.  “You must like it.”

Bella found another pair of pink nylon panties and tossed them over to me.  

“I’ll go open some wine,” she said.

It was our habit to have a couple of glasses after sex, usually followed by another fuck or two. It gave me a little time to recover.

But it didn’t take long that day.  As soon as I slipped into the satin nightshirt and panties I felt my cock stirring.  I went to find Bella. She had just filled two glasses. I took them from her and put them back on the counter.  I stepped behind her and swept her hair to the side. I kissed her pale neck.

“I need to fuck you, Bella.” 

She cooed softly.

“I’m going to take you to bed.  And I’m going to fuck you wearing panties.  Do you like that?”

“I’ve never been fucked by someone wearing panties,” she said in a bratty tone.  “Seems a little feminine. And I prefer alpha men.”

I pulled my hand back and slapped her panty-covered ass hard enough to make her jump.

“I’ll show you how alpha men fuck in panties,” I told her.

We scampered back down the hall.  I pulled her into the guest room. I bent her over the edge of the bed.

“No,” she protested.  “I want to watch.”

She turned back over.  She unbuttoned my silky nightshirt.  My cock was bulging in the pink panties.  I pushed them to the side and my sprung my cock free. Bella slid her panties over to expose her pussy.  

She was so wet that my cock slid right in.  She gasped with delight.  

“You’re fucking me in panties,” she said.

“You like that?  You like my dick hanging out of my panties?”

“Yes.  Yes!”

Her eyes were glued to my glistening cock splitting her pussy wide open.  

“You’re going to cum for me,” I told her.

“Yes,” she said.  “Yes.”

I pumped my cock into her.  Her tits bounced beneath her camisole.  Her face grimaced. She called out my name as she came.  

“I love it when you fuck that hard,” she panted. “It’s like you own my pussy.”

“You’re going to ride my cock now, Bella.”

“Will you keep your panties on?” she asked.

“Of course.  But you’re taking that top off.”

She quickly obeyed.  She straddled me in her white panties, garter belt, and stockings.  My silky nightshirt was still open. She pushed my panties aside again.  My cock was still wet from being in her pussy. Bella pushed her panties aside and got on my dick.

I put my hands on her big titties.

“Ride that cock, Bella,” I said. “Ride me while I’m wearing panties.”

She was normally slow and sensual on top.  But that night she got wild. She put her hands on my chest for leverage. She squeezed my cock with her pussy muscles.  She moaned loudly. She got herself off quickly.

I rolled her onto her back again.  She wrapped her legs around me.

“Fuck me,” she pleaded.  “Fuck me like a man in your little panties.”

I plowed her pussy.  Her headboard bounced off the wall.  Bella squealed loudly.  

Her pussy felt like heaven around my cock.  

“I’m going to cum in you,” I told her.  

“Please cum in me,” she begged.

I couldn’t hold out any longer.  I filled Bella’s pussy with my cum.  

We laid next to each other in bed in our panties and stockings.  

“So are you going to wear my panties all weekend, or it just a sex thing?” she asked.

“I wouldn’t mind wearing them all weekend,” I said.  “But it will keep me constantly horny.”

“Well then you should definitely wear them all weekend,” she said.  “I’ll lay out a few options for you.”

“You’re incredible,” I said.

“I know.  But you have to do something for me.”

“What is it?”

“You mentioned you’ve fooled around with other guys who like to crossdress, right?  I want a threesome.”