First Time with a CD  

RedheadedPeg 26M
1 posts
2/11/2019 10:48 pm
First Time with a CD


The Internal Urge:
I initially developed an interest in M2F transgender ladies, fembois, and CD’s when I was -years-old through internet pornography in 20. My interest developed behind closed doors and tended to focus on amateur work with an emphasis on transitioning bois to pre-op full-breasted gurls. I’ve never enjoyed the scripted scenes or barbie-dolls like the current Kimber James or Sarina Valentina. However flat chested Bailey Jay, Chanel Santini, Lily Demure, and Sasha de Sade still drive me wild. I suppressed my kinky side as I grew up and occasionally would smoke a little marijuana and masturbate to the idea of meeting a woman at a party who would drop hints about having a penis as we flirted.

The tilting point:
I went about my daily life as a heterosexual until I turned 20, roughly a sophomore in college. I joined DateEtc - Hookup and Find Sex Now with a $50 visa gift from Wal-Mart, back when the site still let you a gold with a gift in 20. (I had parents that still occasionally put into my bank from time-to-time so I tried to avoid using my debit .) I have never had any social media accounts, still don’t with the exception of DateEtc - Hookup and Find Sex Now, so this was a big step for me. My urge to meet a gurl drove me to post pictures of me in every which way, including my , and I checked my daily for almost a month. I exchanged emails almost daily with a transitioning M2F from Loveland that I was hoping to meet. However, it was a quick message from a visiting CD that would end up being my first.

Meeting Laura:
Laura was a 6’1’ 2lbs CD who wore a long brown wig, cherry red lipstick, turquoise blush, black eyeliner with blue eyes, and darker blue corset with fishnets that led down to her 2 inch black heels. She probably had an 8 inch circumcised penis from the initial picture she sent and I was sold. She messaged me on a Thursday to invite me to the Red Lion hotel on that Friday at pm. She was coming for a work meeting that weekend and wanted to have a little fun after her meetings ended. I became rock hard reading her email and my desire to be with her overruled my fear of being a first time bottom. I was 5 lbs, 5’, and had long red hair that went down to my chin. I had always been a top with girlfriends throughout my life and enjoyed anal, vaginal, and oral sex. I anally fucked myself for the first time that Thursday night with an old toothbrush. I stayed rock hard for over an hour as I played with the vibrating handle thinking about the night to come. I ended up cumming in my hand and licked it afterwards. It was the first time I had ever tasted cum and I liked it. I wanted to be the best bottom I could and mentally reviewed all the things I had loved about doing anal with past girlfriends. I would be eager. I would let her put her hands on the back of my head when I gave her a blowjob. Yes, I would give her a blowjob and I would let her cum down my throat if she couldn’t resist. I would have anal sex and I wouldn’t ask her to stop, no matter how much it hurt. I would lie and say I loved anal, even if it hurt. I would hold my legs up if needed and try not shake if I fatigued. I wouldn’t masturbate on Friday before we met because I wanted her to make me cum. I wanted her to continue to fuck me, regardless of my ejaculation, until she came. I would let her fuck me. My mind thought of all the different ways she might cum as I shaved myself clean in every way. She sent me a second picture of her on Friday morning and I knew I was committed. I was supposed to go to room #6 and knock on the door around :30pm.

Sex with Laura:
I went on a 6 mile run that afternoon to make sure I looked as thin as possible and I was rock hard as I knocked on the door. Laura opened the door and I walked in to be overshadowed by at 6’3’ 2lbs CD who looked exactly like the first picture she had sent . She had long brown hair, cherry red lipstick, turquoise blush, black eyeliner with blue eyes, and darker blue B cup corset with fishnets that lead down to 2’ black heels. I reminded myself of the expectations I had set for my behavior and I immediately leaned in to kiss her. Her lips were bigger than I had imagined and some of her lipstick rubbed off on my lips. I could tell she was surprised and she walked over to the table to take a drink of what I assumed was a mixed whiskey drink. I could tell she thought about offering it but didn’t because I assume I looked barely 18-years-old. However she did ask if I smoked marijuana and I happily pulled out a little loaded chillum I had in my jacket. I took a , kissed her again, and gave her the pipe. She it and I hoped in vain that she would kiss as she exhaled.

I reminded myself to be eager. I pressed my body against hers and slowly moved my hands down from her neck to her breasts. They were hard like pin cushions but I imagined they were as soft as my most ex-girlfriend’s natural D’s. I was happy she had breasts and reaffirmed that she could fuck me if she wanted. My hands wandered down to her penis, the main event, and Laura kissed me as my hands reached her blue panties. Her hands clasp the back of my head as she kissed me and I moved on to my next objective. I would give the best head I could, regardless of it being my first time. I let her penis and my spirits rose as I realized she was actually only 6 inches.

She lay on the bed and my mouth went to her dick. My nose was soon pressed against her pubic symphysis as she thrust into my mouth. I was doing a good job and I was rock hard without having touched my penis. I kept telling myself that I would be enthusiastic as she kept thrusting into my mouth for to 20 minutes. I would swallow if she were to . She thrust deeper and let a toned “fuuuuuck.” I responded by starting to kiss my way up to her corset, then to her fake breasts, and then to her luscious lips as I straddled her hips with mine. She wasted no time and reached for the lube on the nightstand. I kept kissing her as she lubed her dick and pushed it into my ass. It was so quick and it hurt so much. I kept telling myself that I would be the perfect fuck for her. She felt huge inside me and my clean cock lay erect on her corset. My hands went to her breasts and I again imagined them to be natural mountains. I immediately started to rock my ass along her dick as I continued to feel up her breasts. I would bear through the pain in order to be a good fuck.

Both of her hands went to my hips and she clenched me with each thrust. I was glad she was only 6 inches at this point as she perfectly filled me each time. My erection grew bigger with each thrust and it was now bouncing off her corset. I leaned back with a hand on her thigh as she continued to thrust and wrapped my left hand around my penis. God she felt good. My mind wondered if I would later have handprint bruises on each hip from the way she was gripping me and I resisted the urge to stroke my penis for fear of ending the sex with a premature explosion. Her thrusts increased in frequency and amplitude, as did the bobbing of my cock on her chest.

Her left hand went from my hip, to my chest, back to my naval, and finally to my penis. She didn’t grab it but rather kept it from bouncing. Her right hand still tightly clenched my hip to ensure she drove deep inside me. We must have been fucking for minutes now and I wanted to ask her for more lube as it started to hurt. My mind returned back to being a perfect fuck though and I promised myself that I wouldn’t bring it up. She was barebacking and deserved the friction my expense. Her hand finally started to wrap around my penis and I worked to fuck the entire length of her dick with each thrust. I was trying my best to last as long as I could but her hand was going to make explode. After 20 minutes of enduring her thrusts, her hand made explode. It was the biggest release I had ever felt, mixed with a feeling of failure. I had first but it didn’t matter to her. Her left hand went back to my hip and her thrusts became short rapid poundings. I was truly in her hands and she owned me. She went as hard as she could for another minute with her hands digging into my hips. I had every last drop of milked of and constantly resisted the urge to tap . The blood began to leave my penis in throbs just as she exploded into . I felt the ropes of deep inside. Her dick throbbed harder and I felt the ripples move inside as well. I kissed her and she kissed .

My mind jumped to the fact that I had just been barebacked by a CD I had never met. I let her control the room though and she thrust a couple final times as she continued to flood me. When she pulled , I kissed her and then immediately went to the bathroom. I tried to defecate but was unable. I stuck my finger in my butt and felt her . I wiped the with tissue and accepted that I was her fuck as I emerged from the bathroom. I lay next to her and kissed her one more time. She asked me if I wanted to drop of and move to LA with her. I laughed it off but it was a nice thought. I waited until she sat up to see if she would ask for another fuck. She didn’t prompt so I quickly dressed and moved for the door.

Afterthoughts:
She handed my chillum and that was the sign I needed to leave the room. I got into my car outside and prayed I didn’t have HIV. I also hoped my friends wouldn’t notice my cleanly shaven legs in the month to come. I then noticed that she sent me a saying I was the best fuck she had ever had. I succeeded in my goal of being a good fuck but I drove home in a mess of emotions. I loved what I had just done but recognized that everything I had done was based purely on an urge, without an ounce of rational thought. Thank god my HIV 1 and 3 month tests were negative, along with the rest of my STD panel. I deleted my DateEtc - Hookup and Find Sex Now for the next couple years.

Gina_L07 62T
338 posts
2/16/2019 9:02 am

Nice story. I bet you were hard and came several times while you were writing it. I get that way when i write about my exploits. I totally understand the anxiety too. I had my first BJ and anal sex in the 80s and the lust to do it was greater than the logic of using protection. Fortunately like you I was spared. Just curious, how bad did your legs itch when the hair started growing back. I remember those days too. Take care and do play safe. Ciao.

Gina {=}


RedheadedPeg replies on 3/30/2019 1:13 pm:
My legs did itch a fair amount when the hair first started to grow back. I'm glad you liked my story! =)

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