I Cross-dress for My Older Friend Gf

1

When I was 19 I dated a girl who was 35.

Dated is too strong of a word. We were just fuckbuddies.

Her name was Katy: She was short, blonde, and medium perky tits. They looked like Hershey kisses. Her nipples had this sexy upward angle to them when she was aroused.

Katy asked me for my phone number one night as I walked around the downtown bar scene.

I live with my Dad in a cool area of the city. When I can't sleep, I walk around and see what's going on.

Anyways, Katy and I started talking just outside a cool, hip, trendy bar.

Katy gave me her phone number.

Later in the night Katy texted me and told me to meet her at another bar in the area.

I arrived and met Katy outside the bar.

She was alone.

I told her I was 19 and Katy laughed.

Katy and I went and got cheap shitty pizza..

I need to get a fake.

Katy and I ate our shitty Pizza and then Ubered back to her place.

Katy put her hand on the inside of my thigh in the Uber.

Her hand inched up my leg as we got closer and closer to her apartment.

Katy and I went straight to her bed. I think she was pretty drunk.

We sloppily kissed one another as we undressed.

Katy's blonde hair looked good on her naked shoulders. She looked like a wild animal.

Like a lion.

We continued to kiss as we touched one another.

Katy did this thing where she only rubbed the tip of my penis.

It was a strange, strong sensation.

My hips rocked into her hand.

I touched her perky tits and butt as she teased me.

Katy spread open her legs and pulled me by my penis on top of her.

Both Katy's mouth and the lips of her sex were wet.

Katy's lips tasted fruity, like grapefruit Burt's Bees.

The wetness against our mouths had a parallel feeling to the wetness against our sexes.

I slid in and out of Katy.

I didn't really know what I was doing.

I already wanted to ejaculate.

I held it in, and focused on Katy's breathing.

I mirrored my breath with hers.

Watching Katy's breath helped take the attention away from my penis and on to Katy.

The urge to ejaculate subsided.

I breathed in when Katy breathed in; I breathed out when Katy breathed out; I moaned when Katy moaned.

I was a perfect mirror.

Katy's breath escalated as we fucked.

My breath danced in tune with hers.

I felt connected with her.

Stuck in a quadrille of breath with her.

I followed Katy and I felt the urge to ejaculate once more.

I couldn't stop it this time.

My pelvis took over, and pumped into Katy as hard as I could.

I kept my breath mirrored to Katy's as I orgasmed.

We both moaned together.

Katy's legs and arms wrapped around me so I could not pull out.

She pulled me in deeper and I released.

Katy kissed my neck as the waves of pleasure crashed into me.

It felt so good being inside Katy.

The orgasm lasted a long time.

There were so many pumps.

Post orgasm, I just laid inside Katy as she continued to kiss my neck.

I didn't want the sensation to end.

2

I like older women.

Older women bring less pretension to the relationship.

I knew Katy just wanted to fuck and that was fine.

I didn't feel like I needed to impress her or do anything extraordinary.

Younger girls make me nervous: I feel like I have to be extraordinary; like I have to plan great dates and impress them for no reason.

It feels like there is more expectation in relationships with younger women..

Not with Katy. I felt like I could be myself fully with her.

Maybe this tension is all in my head?

------

The second time Katy and I had sex was exactly one week later.

Katy invited me back to her apartment to drink wine and watch a movie.

I arrived and Katy already had two glasses of Rose poured.

We sat on her couch with the two glasses and bottle, and watched Queer Eye For the Straight Guy.

Katy chose the show. It was actually good.

We finished the bottle of wine in the time it takes to watch one episode.

Katy and I then began to kiss on her couch.

Kay draped her body on top of me.

I couldn't help but to dry hump her a little as we kissed.

My cheeks felt rosy and hot from the Rose.

"Let's go to the bedroom." Kay commanded.

I followed.

Katy and I layed down on her bed and resumed kissing in the same position we were in on the couch.

This time Katy dry humped back into me-- making long full strokes against me through my jeans.

I don't know how Katy manipulated her pelvis to make such full strokes.

She must be good at yoga.

Katy broke the kiss.

"Is it cool if I ask you to do something naughty?"

"Sure, what's up?"

"Well, it's kind of embarrassing, but I've always wanted to have sex with a guy wearing a dress."

I couldn't help but laugh.

Katy explained: "It's just that I saw it in a porno once and I thought it was hot. What do you say, I'll make it worth your while."

I probably would have said no if I was sober.

"Sure, whatever."

"Yay!"

Katy humped me one more time, stood up, and disappeared in her closet.

When she came out she was holding a short pink mini skirt and a pair of white lace panties.

"Strip," Katy commanded.

I took off my jeans and boxers revealing myself.

Katy touched my penis as I pulled the dress on.

"Now the panties."

I slid the white lace frilly panties on.

I am a skinny guy. Katy's clothes fit me well.

The panties barely had enough material so that I could tuck my erection into them.

The material felt soft and lush against me.

"Fuck, you look so hot." Katy said.

I would have been embarrassed if I was sober.

Katy and I kissed as she fondled me through the panties.

"Alright," Katy said, "I asked you to do something, now it's your turn to ask me to do something."

I laid back on her bed. "Can you do that thing where you just rub my tip?"

"Sure, anything for my pretty girl."

"And don't call me that."

Katy laughed.

Katy's skinny fingers reached under my dress, slid the lace panties down around my upper thighs, and her fingers found my sex.

My movement was restricted by the panties around my thighs.

Katy laid back in the bed next to me and we kissed as she rubbed just the tip.

I slid my hand under her shirt and bra.

Her nipple erect in my palm.

The crazy sensation returned as Katy rubbed my tip.

Her lips teased me as she kissed me.

I humped into her hand.

Katy's lips smiled as I began to hump her.

The sensation was so strong. I was so horny. I wanted Katy.

My hand moved from Katy's breasts to her neck.

I choked her as she rubbed me.

I was drunk and maddeningly turned on.

I choked Katy too hard. I couldn't help it.

I rolled on top of Katy. She kept her hand on me.

I slid her panties to the side, removed her hand from me, and resumed to choke her,

Katy whimpered.

She was a loud drunk.

I choked her and pressed her into the bed as I humped into her.

I could not control myself. I needed Katy.

I could not calm myself.

I choked Katy. She whimpered in my ear. I orgasmed.

It was all over quick.

I felt ashamed at coming so quickly..

Katy continued to whimper as I removed myself from her.

"I'm sorry."

"What for?"

"For coming so quick."

"Don't sweat it. It was short, but hot."

Katy gave me a reassuring kiss. "Can you finger me for a bit."

Sure

"Don't stop choking me."

I followed Katy's commands and fingered her as I choked her.

"Fuck yes." She moaned.

Katy's hips humped into my hand.

I didn't finger her that much. I moreso palmed and touched the outside of her sex

My fingers were inside her. But the motion was more in the palm and hand rubbing the outside of her.

She seemed to like it. But Katy was so horny I think she would have liked anything.

3

Katy and I got in the unspoken rhythm of having sex every Saturday night.

We did not hang out at all during the week.

Just sex spaced out exactly one week apart.

------

"I'll let you fuck me anal if you be a good girl and wear your pink dress to Starbucks." Katy said.

"Sure."

I stripped out of my jeans.

Katy touched me while I put the slutty pink skirt and white panties on.

Katy grabbed me by the hand and we walked down the stairwell of her building, down the street, and into a Starbucks.

Katy was very handsy as we walked.

Katy ordered two cappuccinos and paid.

We then sat down in a booth in the corner.

Katy's hand found the inside of my exposed leg.

"You're such a cute boy toy," Katy whispered. "I'm so turned on right now."

Katy and I sipped our coffee as we touched one another's legs.

The booth was nice and secluded in a dark corner of the Starbucks.

For a second, Katy fondled me through my lace panties.

"Let's go," she commanded.

------

Katy bent herself over the marble island in her kitchen and pulled her leggings down around her thighs.

I pulled my skirt up, my panties down, and placed my tip to the outside of Katy's other hole.

I placed my hands on Katy's tiny waist and pulled myself in.

I pressed myself in, seeing how far I could go.

"Fuck," Katy moaned, "please, oh my god."

I held still as Katy grinded and humped back into me.

I just gripped her tiny waist and let her do her thing.

To be honest, anal is not that great.

It's one of those things that sounds great in your head, but doesn't pan out well in reality.

Things got dry.

Katy found some coconut oil in her pantry, rubbed the oil on my sex, and we resumed fucking-- Katy bent over the marble kitchen island.

It felt way better this time.

Things were much more wet.

Oiled up.

The coconut oil gave me a crazy tingling sensitive sensation.

I humped Katy into the counter as she whimpered and moaned"

"Fuck, oh my god, yes please, I'm so turned on, please."

Katy rubbed the outside of her feminine sex as I fucked her into the counter.

It is a great feeling when you are with a girl and you can tell they are enjoying themselves.

I wanted to ejaculate so bad, but I held it.

I tried to take my attention away from Katy's moans and move it somewhere else.

My mind was blank. I couldn't think of anything.

"Fuck, yes, fuck me, your such a good girl."

"Don't call me that." I said.

If I am being 100% honest, I was turned on by Katy calling me her girl, but not ready to admit it to myself.

"What are you going to do about it?"

I gripped Katy's waist even tighter, and pounded into her harder and at a faster pace.

I felt the urge to ejaculate build.

I did battle with this demon: I didn't want the sex to end.

I stayed myself for as long as I could: I felt myself slip and I began to orgasm.

I thrusted myself as deep as I could in Katy.

My whole torso bent over Katy.

I wrapped my arms around her tiny tits and thin neck, as I humped into her and released myself.

Katy continued to rub herself and moan.

I finished, stood myself up, and removed myself from Katy.

My seed spilled from Katy, still bent over the kitchen island.

She continued to rub herself off. I went and found a towel for the mess.

When I came back Katy was orgasming against her fingers into the island.

I let her do her thing. It was hot watching this older woman get herself off.

It's weird how proud men are of their ejaculate.

I looked at my seed spilling down Katy, down the inside of her leg, and felt immense pride in myself.

Katy continued to rub her clit.

I wanted to take a picture.

Katy finished orgasming. I handed her the towel and she wiped herself off.

I was still dressed in white lace panties and a pink short skirt.