First Time I Fucked as a Girl

I just wanted to say this is a real story that really happened to me.

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It was the summer after graduation and I had just turned 19. I was dating this beautiful brunette girl. I liked her a lot! One reason, was she was very bisexual and I loved watching her have sex w/other girls. Plus, we both had a little bit of a “kink side” to us. She introduced me to Ecstasy and the wild fun sex we had while taking it. I couldn’t explain it at first, but when I took the double stacked Root-beers, it would make my asshole completely relaxed and itch for something to be in it.

We started out with butt plugs in each of us. She was wearing a strap-on and fucking me with it. One night, I said to her how lucky girls were, they had a ton of different sexy lingerie we had incredible sex that night. Afterwards standing in front of the mirror, I said how fun it would be, if she helped me completely dress up the next time.

A couple weeks later, I got a call from Amy & she said tonight was the night. While we took a shower, she helped to shave my whole body smooth, sat me down and started putting make-up on me Foundation, then powder, false lashes, black eeyeliner and blending them perfectly. She pulled out a long brunette wig, a bra with “D” silicon boobs in the bra pockets. A black garter belt, thigh highs, and her black 3″ plat form heels. Little black lace panties and a one piece long sleeve top that went into a mini skirt.

All done, she stepped back to admire her work. Even I was amazed at the transformation! Looking at me, Amy said “one last thing before your surprise” and lifting my skirt and sliding in a butt plug. She said tonight is your very special night.

Just then the doorbell rang. Taking me by the hand, we answered it. I was shocked & a little embarrassed to see her boss Ted at the door. Amy greeted him and introduced me as “Amber”. In my best girls voice I said, “Nice to meet you!” As he kissed my hand. Ted then asked Amy is this her? Glancing at me Amy gave me a sexy wink saying ‘yes it is’ to Ted.

By now izmir escort the ecstasy she gave me was starting to very much kick in, relaxing my Asshole to the point the butt plug almost fell out. I excused us to ask Amy what the hell she was thinking? What if he recognizes me? Or finds out I’m not a real girl? Kissing my cheek, Amy then whispered in my ear. Don’t worry he overheard me telling another girl at work about what we did.

After everyone at work left for the day, Ted called me into his office and told me how much it really turned him on. Ted went on to say, that he has had a secret fantasy he never told anyone not even his wife. for over 20 years He always wanted to have sex with a beautiful T-girl. Ted also said he would do anything to make this fantasy happen. Walking across the room as sexy as I could, I stood face to face with Ted. (talking as soft and feminine as I could). Amy tells me you’ll do anything to be with me tonight huh? Ted nodded yes. I then whispered in Ted’s ear, “Amy gets a five dollar an hour raise. As much over time as she wants and medical insurance.”

Ted didn’t hesitate, done!! I knelt down to my knees and started unbuttoning his pants, I could feel him already getting harder. As I pulled his little sexy underwear down I was shocked to see a 8 1/2 in. Semi hard cock pop out. All I could say was OMG! Taking it in my hand. I stroked it a few times, I started by licking his huge cock up and down, it took a couple minutes to work up enough nerve to take it into my mouth and start sucking it. I tried to suck his cock the same way Amy did to me. I heard him let out a moan as he held the back of my head, Ted started to thrust his cock into my mouth making me gag. Then, he picked me up and carried me to the bedroom. He took off my skirt and my panties and took a step back.

As I stared at Ted standing in front of me naked, wide shoulders, chiseled chest and not quite a full six pack abs, his rock hard cock, (that now looked like it was 9 inches) standing straight mersin escort out at me. I then felt a wave of fear come over me as reality set in. OMG!! He is really going to fuck me with that huge cock!.. Grabbing me by my ankles. Ted ran his hands up my smooth thigh highs. He spread my legs. Pulling my butt plug out. He knelled in front of me. My Asshole twitching with excitement. I let out a gasp as I felt his hot cock head press against the wrinkles of my Asshole.

Just as I took a breath. I heard a Pop! And his cock was in! A rush of pain ran through me and I let out a whimper.

Ted leaned forward with my legs on his shoulders, arching his back his head next to mine, I heard him say. “It’s OK just relax Amber”. Next thing I knew his cock was all the way in. his flat stomach pressing against my balls. He started slowly at first, all the way out then all the way back in. My Asshole was being stretched to its max. As much as it hurt, in a weird way, I loved the way it felt. I could feel every bit of Ted’s 9 inch cock sliding in and out. Every couple of minutes he would pull his cock out as fast as possible, holding my cheeks apart and starring at my now gaping Asshole. Next, he rolled me on my hands and knees. Ted stood over me, placing his feet next to my knees. Bending over a little, he took his cock in hand placing it at my now gaping open Asshole. Rubbing his cock head up and down teasing me I heard him say.

“Do you want my cock Amber?”

I begged “YES!”

Does it feel good? Again, I begged “YES!”

I will put it back in if you tell me what you like about my cock being in your Ass? Pushing just the head in I let out a moan. “I like the way it makes me feel so full”! I also like it going in and out! The more I talked the more it was turning me on! Ted said “because you have been such a good girl so far I’m going to give you something extra.” Thrusting his hips in and out I felt Ted’s hand grab my hard cock. As he fucked me, Ted started to jack me off at the same time; sakarya escort it was almost too much!

Little did I know, with me in the “doggie style” position, it put Ted’s cock at the perfect angle and every movement, he was massaging my prostate. Making it pump out a non stop thick white cum liquid. I could tell Ted was getting close to orgasm as he picked up the pace and from the sound of his grunting. Ted held me by my hips as he pumped his cock faster. I felt his cock start to throb & twitch w/every thrust. I knew what was about to happen! I said to him, “Please not inside! Don’t cum in my asshole!”

I tried to squirm away. But Ted held my hips even tighter! Making it impossible for me to get away! Then I felt it!! A rush of really hot liquid being shot into my asshole, with every grunt I heard, and every cock throb. I felt more and more cum coating my bowels. I lost count after the 14th squirt. My rectum now completely full of hot cum! He leaned over and said, “Sorry, but Amy told me I had to do that”.

After a few minutes I could feel his cock starting to soften enough I could push it out. Ted told me not to move, because my Asshole was still gaping open the size of a silver dollar coin. When I stood up, I could feel cum running down my inner thighs. Amy was watching and filming the entire time!

Ted got dressed saying he has never cum that hard with his wife in 20 years of marriage. I reminded him what he agreed to & he said he wouldn’t forget. Saying he would love to take me out on a date next time.

Amy was so turned on, gushing in her panties as she stared at my gaping open Asshole. She was watching and filming the whole time. She bent me over & popped the Butt plug back in my open Asshole, taking off her panties, she laid down spreading her legs in front of me. With my now rock hard ‘cum covered cock’, she guided me into her dripping wet pussy and fucked me for the next four hours.

My Asshole dripped and leaked cum for the next week. Even 3 weeks later, My Asshole still has not closed yet. I keep finding myself every night laying on the bed with a mirror just staring at my Quarter size gaping Asshole as I jack off.

Oh, and Amy’s boss Ted, gave her that raise and even made her a manager. Ted calls to talk to Amber at least once a week. Even telling Amber he would leave his wife if she would be his girlfriend.