They say everyone remembers their first time, and I have a lot of firsts to remember.

But the one I want to tell you about is my first time getting it on with a woman while I was wearing ladies’ clothing. While I’m definitely what you’d call sexually experienced, I’d never shared my frilly fetish with anyone else, and I’d certainly never had sex while dressed up as a woman. But when I started dating Holly, I knew I wanted to let her in on my secret.

We’d been dating for a few months when I decided that I had to tell her about my desire to wear women’s clothing. She came over for dinner at my place, and after our meal, I slipped away to change while she put together the dessert she’d brought for us. I wasn’t sure how she’d react to my surprise, but I’d dropped plenty of hints over the weeks and was sure she would at least be kind about my fetish, even if it wasn’t a turn — on for her.

I had no reason to worry because as soon as Holly saw me, she raved about how “darling” I looked. She made me spin around so she could get a look at me from all angles, and she spent a couple minutes gazing closely at my face and hair, examining my makeup and every bobby pin in my wig. When she finally stepped back to take in the full view with an appraising eye, she was smiling wide and looked like the proverbial cat that ate the canary.

She told me I looked incredible and that she was impressed with how well I’d done myself up, but if I wanted and wouldn’t be opposed, she’d love to give me some makeup tips and help me pick out some flattering new outfits.

“She gave me no time to reply before she sucked my cock into her mouth.”

Whatever I thought was going to happen when I told Holly my secret, it wasn’t that. I excitedly agreed to plan a dress — up date with her so she could teach me all her feminine tricks. But that wasn’t the only surprise Holly had for me. After we agreed to a special cross — dressing night, she kissed me. She was fierce and passionate, and she didn’t waste any time before pushing her tongue between my lips and into my mouth, deepening our lip — lock. At the same time, her hands were roving over my body, and she was soon reaching under my blouse to rub my back and then moving down over my skirt so she could grab my ass.

As she kissed and caressed me, I felt my cock getting hard, and soon my erection was pressing against the front of my lacy boyshorts — and against Holly’s stomach. She didn’t say anything, but one of her hands immediately moved from my ass to my crotch, and she started stroking my dick through my skirt and underwear.

Fooling around with Holly had always been fun, but now that I was able to share all of myself with her, I felt even more aroused. And it was clear she was into my fetish, as well, because while she normally likes a long makeout session with lots of cuddling and kissing, it was only minutes into our lip — lock that she dropped to her knees and took things further.

Holly pushed my skirt up around my waist and then pulled down my boyshorts. She teasingly commented on the obvious wet spot in the front of my underwear from my leaking pre — come, but she gave me no time to reply before she sucked the tip of my cock into her warm, wet mouth.
I could hardly see her under the bunched — up fabric of my skirt, but I could feel what she was doing, and what she was doing was sucking my dick with a voracious intensity. I had to wrap my fists in my skirt to ground myself as Holly’s lips and tongue worked up and down my shaft. She was giving me a blowjob like never before, and I wasn’t sure I would last very long.

Holly was really having fun, though, and I wasn’t going to stop her. When she deep — throated me a moment later, I clenched my hands tighter in my skirt and moaned loudly. I didn’t care if I came too soon, because I was dressed in my favorite femme outfit and was having my dick sucked by my incredible girlfriend. Nothing could possibly ruin that for me, not even a premature explosion.

And I did explode a minute later. I came hard, filling Holly’s mouth, but she didn’t let up. She kept her lips locked around my length and sucked down my seed, and I had to fight to stay standing as pleasure wracked my body.

When Holly finally released my dick, it was still hard, and my girlfriend was ready for a second round. I’d never stayed stiff after an orgasm. Usually I need an hour or two to rebound before I can have another go, but I was so hot from sharing my cross — dressing with my girlfriend that even a massive climax wasn’t enough to sate me.

Holly, seeing that I was still rock — hard and ready, pulled off her underwear and walked over to the couch, hiking up her dress as she went. I looked after her, still in shock from everything that had happened so far that evening, but as soon as she lay down on the sofa, I hurriedly kicked my underwear away and rushed over. I held my skirt at my waist as I climbed onto the couch and then slowly sank my cock deep inside her pussy.

Holly was dripping wet with arousal, and my dick slid easily into her slick center. As I started to thrust in and out of her, Holly’s hands once again began roving over my body, grabbing my ass and wandering under my shirt to stroke my chest. Her hands slipped curiously under my lace bralette and stroked my nipples, and it felt so good to have her touching me there while I was dressed the way I was.

Though I’ve been dressing as a woman in secret since I was 19, I’d never even considered sharing that desire with any of my previous girlfriends. I kept my cross — dressing private so I wouldn’t scare anyone off or risk ridicule. But something about Holly had convinced me that it was time to let someone in on my double life, and I couldn’t have received a better response. She was so absolutely turned on that she was thrusting up against me more than usual, raking her fingernails down my back, and moaning my name constantly.

“I kept fucking her with all I had as her pussy quivered and clenched around my cock.”

I was insanely aroused, too, and though I was trying to take my time, I couldn’t help but pick up my pace and thrust harder and faster into her slick entrance. Being inside her felt good. More than good, really. It felt like nothing else ever had, because finally Holly knew everything there was to know about me, all the important things.

Our bodies slammed against each other rhythmically, but then I shortened my thrusts so I could lay right on top of Holly and kiss her as we fucked. There was something so new and exciting about being inside my girlfriend and kissing her while feeling the lace of my bra against my chest and the soft material of my skirt tickling my ass. The sensations were deliciously heady and overwhelming.

Soon, Holly wrapped her legs around my waist and pressed her feet against my thighs, pulling me as deeply inside her as possible. I couldn’t thrust very hard with our pelvises mashed so tightly together, but I swirled my hips and pumped my ass, stimulating her clit in a way that made her moan loudly.

Holly’s legs dropped as she was overcome with arousal. I kept fucking her with all I had as her pussy quivered and clenched around my cock. She came hard, and I felt every beautiful spasm as she climaxed.

I came not long after Holly. We were both entirely spent, and we stayed on the couch for a while, my softening cock still inside her. We kissed and touched each other as we talked about what had happened.

We eventually got up and had some of Holly’s great dessert before heading off to go to sleep. In the bedroom, Holly asked me to wear my bralette and boyshorts. Then she pulled back the covers and climbed into bed, gesturing for me to join her. She snuggled up to me as soon as I got in bed and rested her head on my chest, right on top of my lacy lingerie. One of her hands moved down and traced the waistband of my panties, tickling the skin of my stomach.

We fell asleep like that, with Holly caressing me lovingly, and when I opened my eyes in the morning, she was already awake and once more exploring the lace — covered parts of my body.

As sunlight streamed across us, we made love in the bed, with me still in my girlie underwear. She’d pulled the crotch of my boyshorts aside to free my erection before mounting it and riding me like a wild woman. Holly climaxed harder than she ever had before. I came pretty hard, too — so hard that there was no chance of me staying stiff like I had the night before. But Holly didn’t mind. By the time I’d caught my breath, she was already out of bed and going through my dresser and closet, trying to find my secret stash of women’s clothes so she could dress me up in a new outfit before our next roll in the hay.

Whatever I’d thought would happen once I finally shared my secret with someone, Holly went above and beyond my expectations. And now, every night with her is as wildly explosive as that first night had been, even when I’m not dressed up in lace and panties. But it’s definitely better when I am.

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