A Day at the Beach

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Danielle's day at the beach leads to "her" first time.
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Bit of background to understand the context. I am Danielle, I am 18, very petite 5" 8 65kg and have long blonde hair. I have been a crossdresser since I was 12.

Australia, it was the middle of summer as I was driving to my friend Kate's house. We had planned to go to the beach as I became more brave in my crossdressing adventures. Kate was the same age as myself and was the only person who knew about my little secret. She caught me in her panties when we were younger and since then has helped me transition to Danielle. I pulled into her driveway and lugged my luggage up her stairs. She was home alone as her parents were away overseas.

She immediately handed me a razor and sent me to the shower demanding I get cleaned up. As I shaved every last strand of masculinity away l, my little cock bounced in excitement. I walked into Kate's room to see an outfit already laid out for me on her bed, pink lace G-string with a matching bra. Short high waisted denim skirt with tight white shirt. As I got dressed I felt like such a little slut, wearing the latest fashion always made me feel more confident outside the house.

Kate returned to apply the finishing touches, makeup nails and hair. She worked as a beautician so her work was very convincing, she slapped me on my sissy ass and said we are ready. We got in Kate's car and headed for the beach. We were off to a small secluded beach which was a 2km walk from the car park to the beach itself. As we started the walk, Kate told me the guy she has been talking to would be coming, Brett. But also that he was bringing a friend, nick. I stopped, scared my confidence had fallen away. Kate convinced me that I looked just as good as any girls she's seen and that I'd be fine. I agreed but still showing signs of fear, inside my heart raced knowing that I'd be flirting with shot straight guy.

We reached the sand and saw the beach was empty except for two guys swimming Brett and nick. We found their towels and quickly changed into our bikinis, I put my clothes back on over the top just to be safe, we decided to go see the boys, Kate introduced me but I was to stunned and dreamy admiring nicks tanned hard body. He was your real surfy guy, tall tanned with long blonde hair, he greeted me with a kiss on the cheek and compliment me on how good I looked, I couldn't help but look into his eyes as he told me, it me feel like such a girl with him checking me out. Kate and Brett waded into the water as nick and I went back to the towels. We just produced small talk before I asked him to sunscreen my back, I paid down and felt him pull my shirt up and unclip my bra.

I loved the feeling f his strong hands stroking my back, I returned the favour to him and gave him more of a massage then anything. I turned him over and squatted over his thighs and I rubbed sunscreen over his chest, I ran my hands up and down slowly getting lower and lower until my fingertips slid below his shorts, I wanted to keep going but fear stopped me, I looked up to see him looking me straight in the eyes as he sat up and put his lips to mine. It felt perfect as his touch slid into my mouth. I stopped him and unwillingly told him I'm not

Like other girls. He slid his hand up my skirt and touched my cock, shockwaves uttered down my spine.

He didn't just touch, he began to play and kissed me again, he didn't care, in fact it turned him on more.

Kate and Brett had begun to walk around the headland so nick picked me up and ran towards the water, I felt so feminine being man handled like a little girl. I pulled off my clothes to reveal my bikini, we waded in just deep enough to cover our waists I felt him pull me towards him as he lifted me to his waists and my legs wrapped around him. We kissed passionately as he massaged my ass rubbing his finger along my sissy cloth through the bikini.

We returned to the towel when I noticed the bulge in his pants. I put my hand on his abs and slower lowered it until I grasped his shaft,

It was throbbing and huge, I dropped to my knees and pulled his clothes down. His huge cock bounced out, it looked atleast 9 inches and thick. I had never been with a guy as. A crossdresser. I immediately got to work rubbing my hand up and down his shaft whilst kissing his tip. I felt him grab my head and force his cool down my throat! I gagged but loved every second, I could feel his dick get harder with every lick.

He pulled me up and kissed me passionately before sliding his hand down my panties and massaging my hole, I got on all fours on the towel as I felt a bead of sweat tickle my hole. His big fingers slid in and out loosening me before I felt his warm tip press against my hole, I reached around and guided him in. The pain was killing but each stride caused overriding pleasure. As he pushed I wiggled my sissy ass back against him. My moans became louder as he slapped his balls against my ass. I've never had such a big cock pound my ass. He got faster and faster before I felt him ram deep and flood my girly ass with his warm load. The feeling was incredible as it filled me. He pulled out and began kissing again before carrying me to the water and cleaning me up.

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AnonymousAnonymousalmost 3 years ago

Like you i started crossdressing when i was about 12 as i had two sisters i had plenty of things to choose to wear and loved being in their school uniforms. I ended up dressing for a friend one day in a uniform and had my first fucking on my bed on all fours with a pleated skirt up around my ass and cotton pants down to my knees and white long socks and i felt so sexy with his cock sliding in and out of my ass totally raw. I played with my cock and as he pulled me onto his cock as deep as he could go i felt his cock twitch as he emptied his load of cum into my love hole and i squirted mine at the same time a him i was in heaven as his weight pushed me flat on my bed his cock still hard inside me. He started fucking me again and the squelching noise from my ass coated in his cum was a turn on knowing i was going to get another load soon. The first of many a nice hard cock to explore my sissy ass and fill my hot hole with semen. Iv enjoyed all sizes of cocks and all ages of men fill me with cock and semen but going out in public dressed as a sissy and being fucked by men for me is the biggest turn on and definately the best sex ever

AnonymousAnonymousover 6 years ago

thank you. That's how I experienced my first. I wore a tangerine bikini with a short beach skirt. I was taking a risk, I had heard it was a beach where sexual trysts occurred, in fact I had seen 2 guys fucking the day before. Nervous, laying down, I heard a deep voice, nice bikini, I turned, a tall guy, bronzed, dark hair, you think so, well it certainly looks good on you. I smiled, he sat down, began talking, I felt my cock growing and then his hand on my ass, I waited, then pushed up, his hand worked under me, feeling my cock, nice as his fingers went under my bikini,one gently touching my lubed hole. I came hoping for my first fuck, I think I was going to succeed. He turned me on my side, threw a towel over us as I removed my bikini bottom. He then moved his cock up and down bottom and finding my hole put an arm around me and pushed, surprisingly my hole opened slowly and he eased into me. He pulled back a little then pushed forward, I felt his cock opening me and then his mouth at my ear, mm, tight , now I am going to fuck you and that's exactly what he did. At first on my side but then he rolled me over onto my front and with his arms under my shoulders moved faster causing my cock to shoot its load into the sand. that did it for him, I felt his cock go impossibly hard and his warmth fire into me. He waited a bit, then rolled me back over onto my side and pulled back. My first fuck, yes there was pain but the pleasure of a hard cock in me was much greater. He got up and left, I was at the beach for another 3 days and was much bolder having my ass creamed by 8 guys in that time. I love a hard cock inside me.

AnonymousAnonymousalmost 8 years ago
Please do more with more detail.

I'm so hard please do more stories like this except with more detail. My thick cock loves these baby.

robin48robin48about 8 years ago
Wish

Nice story

I wish I had beCUM the girl as young guy

Dropping your panties & letting a real guy do you.

AnonymousAnonymousabout 8 years ago

Ignore the haters, they read your story and criticize, wow, imagine what their little world must be like. I decided after leaving school to explore dressing up, it was hard for me, I didn't want my friends to know, my family but finally I went to the beach, under my shorts a bikini bottom and under my t shirt a bikini top. I went down to the far end and after looking around, undressed, I felt good, I was excited, my cock was semi hard. I walked down to the water, then walked back. I saw 3 guys walking towards me, I recognized 2 of them, Gary and Alex from school. They stopped, Dennis is that you, nice top, whats going on, well, you know, no tell us. Rob this is Dennis or should we say Denise, they laughed. Well, who is it, Dennis or Denise, mocking me, come on, lets not waste time here, there are real girls to be fucked. They walked away, I felt humiliated, I put my t shirt back on and lay down. I heard a noise, what now, I looked up, it was the guy they had called Rob. What do you want? Well, first of all I'm Rob, we weren't properly introduced and second I came to apologise for my behavior not saying anything. I looked at him, tall, curly brown hair, not muscular but very lean. Oh, that's nice, thanks. They said they knew you in school, yeh, they were in some of my classes, but they didn't know me like this. Hey, you can dress how you like, not their concern really, anyway for what it is worth I thought you looked ok, good colour choice it suits your nice tan. I stood, you like the colour, tangerine, I thought it looked ok too. Look, I am going to walk further around the point, want to come. I shook my head, yeh, think I will. I draped my towel around my shoulders, what about Gary and Alex, what about them, well what will they think. Don't care much, I walked closer to him and reached for his hand, he took mine. My cock reacted, I looked down, so did his. We walked around past an overhanging rock, there was a guy leaning back against the rock, on his knees another guy had his cock in his mouth. We stopped, said nothing, watching, it was clear when the standing guy came, he held the guys head moving back and forward, then let go. We resumed walking, Rob said sorry, don't be,kind of wish it was me. He looked at me, sure, yes, sure. He moved around under a small rock ledge, I didn't need to be asked and I soon had his cock in my mouth, followed quickly by a huge amount of semen which I nearly choked on. Sorry, no don't be, just that well, that was my first time and it caught me off guard a bit. We walked a bit more, I reached over to his board shorts, wow, still hard, yeh , lets stop for a while. I spread my towel, i got the moisturizer out of my bag, here let me put some on you. Ok, I got him to lay back, I applied some to his chest, stomach and pulled his shorts down and slowly stroked him. He kept touching my bikini bottoms, I then said on me please, I lay down on my stomach, lowering my bikini bottoms to my knees. I felt him apply the moisturizer to my back and was straddling me, I could feel his hard cock resting on me. Put it in me, lifting my bottom, he hesitated, please fuck me. I felt him move back, then position himself, I could feel his hard, hot cock between my bottom,i spread my legs, he entered, pain, wait, he eased back, no stay there, ok and he slowly inched in until he was lying on my back. It hurt, he began to move, it burned but my cock grew, he knelt up and went faster, my cock pulsed and my cum shot out onto the towel. I heard him say, oh fuck and felt him swell impossibly inside me and a warmth deep inside me. It made me what I am now, a cock seeking crossdresser, never regretted it, thanks to Rob who I still know and is married to a beautiful woman.

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