The Taking of Amy

The Taking of Amy

Amy was born Andrew K. Henderson, in a sprawling suburb of Chicago Illinois. In her late teens and early twenties, Amy realized that maybe she wasn't in the right body. She dated women as she was supposed to and even married a biological female and tried to be the man she was supposed to be. But the marriage was never as fulfilling as she had hoped, never bore children, and just a few short years into that marriage, Amy realized, she wanted to be a woman and not a man, and she left that marriage.

Through some soul searching, and the eventual acceptance of who she felt she wanted to be, Amy came out to family and friends. She started slowly transitioning into living full-time as a woman. In conversations with her, she told me this was a hard transformation for her. She was years into her career, had a host of co-workers who witnessed her marriage and divorce, friends she had known for decades, and a litany of people in her life who knew her as Andy. So, her change was very slow, very cautious, and in some cases, very secretive.

I was coming out of another short-term relationship with a female when I met Amy. Honestly and truthfully, I never placed much emphasis on seeking long-term relationships with women anymore, since both of my long-term relationships were miserable failures. Don't get me wrong I had more women than most men could ever dream of, I just never put the energy or time into something I knew was never going to be long-term again.

More importantly, I was Bi-Sexual and had dated a few men, crossdressers, and trans women, before the term was even a household word. And the older I got and the more the women who came in and out of my life the more I felt it was time for me to change directions. Truth be told, I wanted dick again. I wasn't scared or hiding that I wanted a "man", I had just never found anyone I wanted to be in a more consistent situation with. I had no fear of sucking dick, I actually like it. I wouldn't have even minded being fucked, more than fucking. But I had never had a long- or longer-term situation with a "man", so I never had the chance to find out. And honestly, my heart and soul were looking for a situation where I could suck dick often, versus eating pussy (again). And fortunately, I found it.

Amy and I started dating very slowly. We met on a gay/bi-dating site. She was in the beginning stages of her transitioning phase. She had just started wearing wigs because her natural hair was shorter and taking forever to grow out to the length she wanted. She had started hormone replacement therapy and was slowly developing breasts, but at the age of 35, and her body being "manly", all the years prior, made her change very slow. She used to wear padded bras, to make her developing breasts look bigger and fuller. She was not fluent with her voice yet, or speaking more softly or more feminine as she wanted it to be. She surely wasn't practiced in make-up or women's fashion. But something about her grabbed my attention and kept me very interested.

Amy wasn't as manly as some men, almost feminine in a lot of ways. She stood about 5'8" tall and weighed about 180 pounds. She had short brown hair and a thinner (changing) physique. She had deep hazel eyes and a very warm loving face. When I met her, she was already shaving her arms and legs and wearing more feminine clothes, but still had to be in "boy mode" for work, that is until she finally advised HR she was transgendered and from there she never looked back. We were in essence the same height, although I was about 20 pounds heavier and was surely going to be the man of the two of us.

Amy and I took things slow, as excited as she was to have a man, something she had been long for, for years, she also didn't want to be played as some "tranny fantasy" and have her heart broken. And I was loving the new sense of passion in dating someone with a dick again, something I had been longing for. But we were both cautious. I can remember the first night of oral sex between us was in my car after our sixth date. Amy had told me many times in texts and conversations that her two biggest fantasies - as a woman - were to give blow jobs and be on her knees getting fucked in the ass. So, when the first time came around, we were both highly excited, knowing we were going to take those steps together.

On that summer night after a few drinks at the bar listening to the local band, we found ourselves alone in my car. Her shirt unbuttoned, her bra pulled up, her small developing tits out. Her jeans open and her pretty white panties revealing the outline of her hard cock sticking straight up in them. My pants open, my underwear pulled down, my cock sticking out like a flag pole saluting her every move. She went down on me first and was sucking me like she was trying to win a gold medal. Even though she was rather inexperienced at it, she was giving it her all, and she surely wasn't bad at it.

She sucked me until I was really close to cumming, but I wanted to suck her cock too. I pulled her up and away from my dick, kissing her deeply, moaning the words "I wanna suck your dick too" through our kisses. When she leaned back in her seat, I leaned over the armrest and pulled her panties back revealing the cock I had been long-a-waiting to see. I slid her into my mouth and sucked her like I was trying to win an award and before the night was over, we had both cum in each other's mouths and had some fun moving the relationship further. And I promise you, she didn't disappoint, nor did I.

Due to our conflicting schedules, we didn't see one another as often as we wanted to, which developed the opportunity for us to chat a lot by text or phone, and made us long for more, because we couldn't be together as we wanted. Which to me, actually made things develop better. We had the chance to make each other's day better, by the texts and calls, but when we got to see one another, it made things more special because we were actually there together. I really started falling for her and her for me and each time we were alone after that first heated make-out session, the more we advanced sexually we became until we went all the way. Now through all our sexual experience (prior to this story of our first sleepover), we had mutual blow jobs, or at the same time (69) type blow jobs, hand jobs. And eventually, we did cross that line and had anal sex, which was awkward, to say the least. But isn't it always?

But we got passed it and each time, we became more comfortable with things and developed a deeper trust and communication with one another. But it wasn't until she spent the night at my house a couple of months in, that we finally hit that connection I was looking for and that is what this story is about.

Amy and I met at a local restaurant by my house, that we had been to before. I asked her for the date and asked her if she'd like to spend the night at my house. I think she was a bit reluctant about spending the night, but said yes. When I saw her coming across the parking lot wearing a beautiful dark amber dress, with nylons and her high heels on, my heart skipped a beat. This was the most "feminine" I had seen her dressed. Of course, she wore women's clothes but never had a dress or nylons on, so this was overly stimulating for me. Upon greeting her at the door with a soft-lipped kiss, I was taken aback by the soft perfume she was wearing. Her gold necklace with a cross hanging around her neck. Her nails were longer than usual, painted blood red, and my favorite wig of hers, with its hair hanging a few inches past her shoulders, styled and glowing. Her make-up was perfect, and she looked amazing.

After dinner we took a long slow stroll around the local recreational walking park, hand in hand, stopping every now and then to hug and kiss, just as lovers do. And I was so engrossed by her and her femininity, that I almost forgot, she had a luscious cock hanging between her legs. As the night drew later and I knew it was time for us to head back to my place, I got extremely nervous. Not nervous, that someone was coming over to have sex, or even spend the night. I got nervous because someone with a cock was coming over to spend the night, which is something I had never had before.

Amy followed me in her car, back to my place and we opened a bottle of wine. I could tell by her mannerisms, that she was just as nervous as I was, as I don't think she ever had an overnight with a man. We sipped our wine, held hands, talked, and lightly kissed, knowing that sometime soon we'd be naked in bed having sex. And as nervous as I was; I wanted her dick so bad. In the few months, we had been dating I had only sucked her off a few times, but somehow those few times had made me want to blow her every time we were together. And of course, I wanted her sucking me. Hell, to be honest, I wanted her to fuck me, make me suck her, and have me cum where ever she wanted. Moreover, I wanted to do the same things to her. Like I said earlier in the story, I wanted dick, but more importantly at this point, I wanted her dick.

As we kissed more and more deeply, I unzipped the back of her dress, allowing room for my hand to slide in and out of the front of it, caressing her developing breasts. My dick was rock hard, nestled deep in my pants, as I hooped hers was in her tight panties. Amy slid the dress off of her shoulders, letting it fall onto her lap, while I unhooked her bra. Her soft, little tits sprung free and my head dropped to her chest, kissing, caressing, sucking, and licking her nipples. Amy moaned in pleasure as my hand started sliding further and further up her inner thighs. I couldn't wait to feel her hard cock and see it popping out of the top of her panties. Her hands rested on the back of my head until she pulled my face upwards to kiss her again.

Our kissing was so deep, so loving and so passionate, that it swept us both up in the moment. Amy leaned me back onto the couch and kissed along my neck and ears, her hand slowly sliding up and down my thighs. Her hand reaching my crotch, feeling how hard my cock was. She slid off of the couch, kicking her heels off, spreading my legs apart, and smiling up at me as she started to reach for my belt buckle.

She quickly got my belt open, unbuttoned my pants, and started to pull my pants down. Her hands followed up, by pulling my underwear down. Her eyes gleamed with excitement as she stared up at my hard cock. She tied her wig up with a ponytail holder, and dipped her head down, putting my hard cock deep into her mouth.

Her head bobbed up and down and she was pleasuring me, while my hands rubbed lightly across her naked back. My mouth was watering, wanting her cock in it. I moaned softly on occasion letting her know how wonderful it felt as she was blowing me. She was down on me for a while, sucking as hard and fast as she could. Taking brief breaks to suck my balls, jack me off by hand or just tease the tip with her tongue. But the more she sucked me, the more I wanted to suck her dick. When it became so overwhelming, I moaned;

"I want your dick."

Amy sucked for a few seconds longer but pulled her mouth away from my dick and stood up.

She pulled the dress down past her hips, letting it drop to the floor. She stood there in her pantyhose and hot pink panties she had on underneath. I unbuttoned my white dress shirt and started sliding it off, as she lowered her pantyhose, stepping out of them and pulling her panties down. Her cock sprung out as it was being released, poking straight out, hard, excited, and ready to be played with. It was an incredible sight to see a beautiful woman, with her long brownish amber hair, her tits resting at her chest. Her smooth shaved body, long red nails, and a big hard cock sticking out waiting to be sucked off.

I edged forward to the edge of my couch as she stepped forward. Amy pulled the back of my head downwards and slid her hard cock deep into my mouth. I moaned deeply in pleasure as it slid all the way in. I heard Amy whimper, at the feeling my warm wet mouth encompassed her cock. I bobbed back and forth sucking her cock, knowing this is exactly where I wanted to be, alone with her, naked, unafraid with both of our hard cocks being played with, coupled by her spending the night.

I sucked her hard and deep, feeling her long perfect shaft slide in and out of my mouth. My watering mouth was the lube that made her slide in and out smoothly. Seeing that perfectly shaved skin, her balls swaying back and forth, her hips slightly swaying as her shaft slid in and out of my mouth. My cock was still rock hard wanting to be sucked and wanting to be inside of her.

Amy stopped my momentum and assisted me up and off of the couch. We came face to face, both of us naked, our hard dicks touching, our chests pressed against one another as we kissed deeply. This was beyond any fantasies, any of my alone dildo play time, or any porn movies I had seen. This was in essence two men; one in transition to womanhood, with two perfectly similar-sized cocks, two people who wanted each other, and wanting dick more than anything. It was perfect!

I guided Amy by the hand to my bedroom, where we continued kissing and fondling each other until she kissed her way down my chest, to my hard awaiting cock. She slid my hard cock back into her mouth and began sucking me even more. I could see her hand wrapped around the back and I knew she was playing with her ass, getting it all ready for my cock.

When she was ready Amy pulled my dick from her mouth, grabbed it with her hand, looked me deep in the eyes, and said, "fuck me."

She got onto her knees and I got up onto mine and I climbed in behind her. I lowered my head and began kissing her ass cheeks. I nudged in between them and started swirling my tongue around her asshole. I wanted to eat her out like I was eating pussy. And although it wasn't the first girl's ass I ate out, it was her first time.

I liked and sucked and swirled my tongue around her entrance, feeling her body react. Listening to her moans and groans and repeating things I felt stimulated her. I reached around her a few times with my hand stroking her cock, or caressing her balls. I can't even tell you how many emotions were running through me. Fear, excitement. Lust. Passion. Fear of being gay from here on out, but so hard, ready, and willing to change teams.

I pulled away from her saliva-soaked ass, reached over to my nightstand, and grabbed some lube. I used a bit of lube and rubbed up and down over her ass, hearing her gasps I was teasing her. I rubbed some on the tip of my cock, edged in closed, and slid myself deep inside of her. I slid into her, like sliding into a wet pussy. This time there weren't any mishaps, misses, or bad angles. This time I went all the way in and I was beyond hard as I started sliding in and out of her.

She was tight and warm and I was holding the outside of her hips as I thrusted in and out. I would look down on occasion to watch myself slide in and out of her. Hearing her whimpers and moans. I was giving her one of her biggest fantasies of being on her knees and being fucked in the ass. And I was loving it! I was so excited and so turned on that I had only been in her for about five minutes when I was so ready to cum.

"Amy, I am so close, but I don't wanna cum yet." Sprang from my mouth.

"Just cum in me baby." She replied back.

With my need to explode and per her wishes, I started pumping her harder and faster, until I came deep inside her ass. She knew I was coming and was whimpering and chirping from the excitement of knowing I was cumming inside of her. I was disappointed in myself that I had cum so fast, but so excited that I got to suck her cock, fuck her, and cum inside of her. But my cock sucking wasn't over for the night apparently.

After I withdrew from her, Amy swung around to kiss me. After we kissed deeply for a long time, both of us on our knees, our dicks still partially erect and hanging out. She pulled away from me, laid flat on the bed, and whispered, "I need to cum too."

I leaned down, bending over at my waist, slid her cock partially hard cock back into my mouth, and started blowing her again. It was extremely exciting to feel her become completely hard in my mouth as I sucked her cock. I must have taken that cock as deep into my throat as I could ten times because each time I did, she would chip out in a high-pitched wail, which turned me on even more.

"Mike" she moaned out time and time again, as I bobbed up and down on her now big hard, slippery wet dick.

"Mike...Fuck! I'm gonna cum. I'm gonna cum."

And before she could get the third warning out of her mouth, she began to fill my mouth with her warm, salty, sticky cum that was shooting from her cock. I kept bobbing up and down getting squirt after squirt of her cum until I had a big mouthful, swallowing it all down. I kept her cock in my mouth longer than usual, just feeling her throbbing and pulsing as she was coming down from her orgasm.

When I finally pulled her cock from my mouth, she pulled me up to her, laying me across her body, and we kissed deeply and longingly, just embracing one another. I knew right then and there; I wanted dick more than pussy. I felt gay, I felt this was all taboo. But it felt right. I wanted every bit of blow jobs, cum, and anal sex we could dish out.

We eventually changed positions and she laid her head on my chest as I laid on my back. Her right leg over my legs, her cock pressing up against my skin, her hands wrapping around me as best she could, and her real hair on top of her head, right under my chin. Shortly after, I knew she had fallen asleep, so I managed to get her a bit more situated and covered her with a blanket. I was still so horny and so enthralled by fucking her and sucking dick that it took me forever to fall asleep.

As I lay there in thought in the quiet of my room, her naked warm body next to me, my mouth still tasting her cum, my cock still partially hard, I realized, I was falling in love with her. There was no denying it. This was no fling. I loved this. I wanted her cock. I wanted to fuck her in the ass. I wanted her to fuck me in the ass (she hadn't at that point) and I wanted this to continue. I knew I had to come out. I couldn't hide this. I couldn't hide her. I decided it was her I wanted! Her dick! Her tight ass! And all her imperfections and upcoming further transitions, she was going to go through. I wanted it all. I wanted her to be my lover. But the next morning held the best unexpected, uninhibited, loving, erotic, spontaneous sex, I had ever had with someone who had a dick. And I knew after; that Amy and I were now going to be a couple for a long time to come.

I'll tell you about that day in the next chapter.

To Be Continued...