tagTransgender & CrossdressersJourney Down the Rabbit Hole

Journey Down the Rabbit Hole


He looked so frail and vulnerable laying there. I knew that my friend Anthony was troubled, but I never knew he would do something like this. Good thing the doctors got his stomach pumped out in time. I have known Anthony since elementary school and he was always different. Shy and introverted was the norm for him. He never really fit in anywhere. Seemed the only time he came out of his shell was around his Mom, his sister or me. Anna and I dated for a while, but we just sort of grew apart. So Anthony and I hung out together till High school graduation. I had enlisted in the Air Force on the notion that I would get the training I needed for a civilian career. I had just been discharged from Uncle Sam's employment and was about to start a new job when I got the call.

His Mom sounded so desperate over the phone. She pleaded with me to come down to the hospital to see him. I wanted to get back in touch with Anthony anyway. I didn't even think twice. After hugging her and Anna, and participating in a mutual consoling section, I sat down in a chair while the two of them took a break to get coffee.

I looked at his face. It was always lean and strangely angelic. I had seen pictures of his deceased father and he definitely favored his mother Alice. He seemed peaceful, almost childlike. His long dark hair, was pulled back in a pony tail. I thought back over the years of our friendship. I was so glad that the doctors were in time. He stirred.

I took his hand and he looked up at me. His expression was half elation and half shame. "T--Troy?" He turned away from me.

"Why Anthony? Why did you do this? You had us worried."

"You don't know what it's like Troy. I don't seem to fit in anywhere. Everybody else has a life but I don't." Tears tracked down his cheeks.

I couldn't be mad at him. "Well Bud, good thing I'm going to be around because if you try that again and I'll kick that Puerto Rican butt of yours down the block."

Anthony brightened up. "You mean...?"

"Yep, you are stuck with me. I am honorably discharged out of the Air Force and I start work at a security and logistics firm, here in town, next week. So I'm going to be keeping an eye on you." At last Anthony smiled.

Because of his suicide attempt, Anthony was ordered by the court to have psychotherapy. I tried to make it to his house to visit, at least once a week. I was always treated like part of the family. Mrs. Gomez made wonderful meals and I had a standing invite for supper any day. I don't know if it was because I was over often or what, but Anthony seemed cheerier somehow. Anthony stayed in therapy long past the court mandate; in fact he started seeing another therapist as well. I found this curious, but at the same time I was pleased at his progress. He laughed more often and the family in general seemed happier.

One evening Anthony popped over to my apartment unannounced. It was a year almost to the day of his attempt on his own life. I had been real busy as of late and hadn't been over to the Gomez household for almost two months. I had just got in and saw someone in front of my apartment door. I thought it was a chick at first, in fact it took me a few moments before I realized who it was.

"Anthony? Hey buddy, how you been?" The person before me looked neither male or female, but sort of an amalgam of the two. He wore a hoody and jeans.

"Hi Troy. I've... been okay. Can we talk?" I nodded and open the door. I followed him inside and pulled a couple cans of soda from the fridge. We sat at the kitchen table. The light was better than in the hallway. His face had cleared up and he seemed softer somehow. His eyelashes looked longer than I had ever seen them before. In fact, his eyes were sort of pretty. I just sat there.

"Do I look different to you?" He had a wry smile, that projected more confidence then I had ever seen from him before.

"A bit Anthony." I was afraid to say anything more.

"You know I continued seeing a psychiatrist." I nodded. "I discovered something about myself. Through talking with the Dr. I found out something. It seems my brain is hardwired as female." Anthony paused to let this sink in. "Makes sense really. It explains why when I check out girls, that I feel a twinge of jealousy and why I like looking at guys asses. That really use to bothered me."

I listened to him; half in shock and half in curiosity. He was different somehow. Even his mannerisms and gestures were smoother and not clumsy as usual.

"Mom and Anna are okay with it. They surprised me by being so supportive. I started hormones, almost a month and a half ago. I feel so alive, maybe for the first time in my life." His eyes narrowed. "Aren't you going to say anything?"

"G--Good for y-you." I stuttered. I was flabbergasted. In my wildest imagination, I could have never come up with this scenario. I looked into Anthony's soft brown eyes. It was like there was this beautiful creature, that was slowly emerging.

"I've been in girl mode for close to a month. I dressed in my old clothes tonight so I wouldn't startle you too much. So you are cool with this?"

"S-Sure A-Anthony." He/ she smiled in relief. "I want you to be happy, Anth--."

"I am changing my name to Alison Marie, Troy." She interrupted as she stood up.

"T-That's an nice name, Anth-- I mean Alison."

"I need to use your bathroom. Be back in a jiff."

To say I was stunned was an understatement. Anthony was always different, even around me. This was the most confidence he had ever had to my knowledge. I have heard about transgender people before, but that it would actually be one of my friends really floored me. Don't get me wrong, I am a live and let live kind of a guy. It's none of my business to tell someone else how to live. To me all people are equal and have equal rights.

Minutes later Anth- I mean Alison reemerged. I stood and was totally stunned by his/ her appearance. I mean, the hood on the sweatshirt was pulled back and he; I really couldn't say he anymore; she was wearing makeup. Her hair was gathered back in a ponytail and was very attractive. Her eyes were beautiful and her lips...What the fuck am I thinking?

"I hope you don't mind. I feel naked without makeup now." As she approached, I could smell the fragrance she applied. She leaned over, kissed my cheek and winked. "See you around Troy Boy." Moments later Alison was gone.

"Curiouser and curiouser." I said to myself.

Another month went by till I found myself at the Gomez residence again. Anna called me up and told me that her Mom was ticked cause I hadn't been over for dinner. I had been holding off because of my strange encounter with Anthony/ Alison.

Mrs. G let me in and hugged me. "About time you showed up Troy. I was beginning to think you forgot about us." We entered the kitchen. Her dinner smell extraordinary. "I hope you don't mind Italian, Troy"

"No, Mrs. G. It smells..." I felt a tap on my shoulder. I turned and Anna threw her arms around my neck and hugged me.

"Hey Troy. Glad you could make it." She seemed more affectionate than usual. Like she was really pleased. When we stopped dating, it sort of cooled down fast, but this was more like the old Anna.

"My turn, Troy Boy." Alison appeared as if by magic. She; there was no getting around this; she was beautiful. She was wearing hip hugger jeans and a pink, belly T shirt. Alice had her ears pierced with hoops, she smelled fantastic and her long, dark hair was done in 'gypsy' curls. Her arms flew around my neck. My own arms went around her waist out of reflex. She kissed my cheek.

I heard a soft giggle behind me. "You two want to be alone?" Anna piped up.

Alison, still in my arms, gave me a saucy wink. "Well, now that you mention..."

"Wow, that food smells great!" I interrupted. By now I was probably as red as a fire hydrant.

We sat down at the table and soon our plates were filled. Mrs. G fixed stuffed shells, salad and breadsticks. Her cooking was wonderful as always. I gazed at my dinner companions. I am attracted to Hispanic women to begin with and their Puerto Rican heritage certainly fit the bill. Even Mrs. G, in her mid forties was still hot. But what killed me was the startling resemblance of Anna and Alison to each other. They were born twins, but since Antho- Alison's transition; they looked almost identical. Even their voices were similar.

"Well, what do you think of our Alison?" Mrs. Gomez seemed quite proud of her new daughter. I quickly crammed a huge bite of food in my mouth, giving me time to think of an appropriate answer.

"I'm getting my boobs next week." Alison blurted. I choked on the bite of salad. Alison, who was setting next to me thumped my back with her hand as I tried to cough up the food.

"I think you startled your boyfriend Alison." Anna giggled. I began to cough in earnest.

"Now Anna. We mustn't tease Troy like that." Mrs. Gomez remarked. But that didn't stop her from smirking.

After dinner and when the dishes were taken care of, we played cards. This was at a card table in the other room and one of the three was playing footsy with me, off and on all evening. I never did find out who. I hoped the Hell it was Anna. Because it would be really awkward if it was one of the other two.

Sometime after midnight, Mrs. Gomez and Alison got to the point where they couldn't stop yawning. They both excused themselves and Anna volunteered to walk me to my truck. Outside she raised up and kissed me on the cheek and headed back into the house. She was so beautiful. I wondered if she would want to get together again and start up the old flame.

I slid behind the wheel and stopped when I saw that Anna had come back outside. She walked up to the car and I jumped out. "Hey Anna. Did you want something?" In one fell swoop, she slipped her arms around my neck and soon her lips were pressed up against mine. I forgot how great of a kisser she was. I wrapped my arms around her waist and really sunk into the moment. Her tongue slipped into my mouth and the race was on. Her tits were pressed up against me and she felt so good in my arms. Anna reached behind her and pushed one of my hands down to her ass. She moaned when I grabbed her other cheek on my own. All the while she was grinding her hip into my growing erection. There was a time, back when we were first dating, that she was almost insatiable. This was just like then and man, did I need it!

Anna backed off and reached behind my front seat for the sleeping bag I kept there. She giggled and took my hand, leading me back to the bed of my truck. I can't remember how many times we utilized our 'fuck station'. But it was real handy and it stayed mostly empty for spur of the moment use. It had been a while, it appears it was time again to test out the truck springs.

Soon the bedding was unrolled and we were kissing again. I reached for her breast and she batted my hand away. "Let me do all the work." She whispered lustily. Well, it was okay by me. I lay on my back and she straddled my body. Anna's hands held mine to the truck bed as her tongue was crammed down my throat. She wiggled her ass against my engorged cock and undid my shirt buttons, one by one. Anna slid down and sucked on my nipples, as my erection threatened to gore her stomach.

"Oh, somebody's happy." She whispered. She slid down some more and undid my pants. They disappeared as if by magic along with my briefs. Soon my hard cock was in her hands and Anna started stroking me. Her hand worked me over good. It was slow and steady. Every time I was close, she would clamp down to avoid the inevitable. "I'm going to suck you now."

Anna kept a firm hold of me to keep me from coming, all the while she slathered my cock with her lips and tongue. It was pure torture and I need to cum so badly. I tell you, I think interrogators use the wrong tactics to get information. Christ; I would have been willing to give her anything I had if she would just let me cum. Finally and mercifully Anna released me and I shot into her mouth over and over. I damn near passed out, it was so intense. It was hard to tell in the low light, but I had the feeling that she sucked down every drop.

"Did you like that, Baby? She whispered.

"Fuck yes, Anna." I fought to catch my breath. "Come up here and I will eat that sweet pussy of yours."

She slid next to me and we kissed. "Sorry Baby, but it's my time of the month. Maybe next time. It's getting late." She kissed me again and whispered in my ear. "I love you Troy." And like that, she was gone.

I laid there, mostly naked and felt like I had just survived a hurricane. After a few moments I slipped back into my clothes and started for home. It seemed that Anna was even wilder than she use to be and that suited me just fine. That was the hottest blowjob I had ever gotten. I wondered how long it would be before I could return the favor. I hope not long.


I got busy again. Another month and a half vanished and I was out of town for most of those six weeks. I thought about Anna quite often. I mulled over her last words to me. 'I love you Troy'. It's not that I couldn't appreciate what she professed, but I had to spend a lot more time with her before I could feel the same. And I didn't want to take advantage of her, more than I already had.

I finally returned home and I decided to give Anna a call. Before I flipped open my phone, it went off. "Hey Troy, how are you?"

"I'm good beautiful. I was just thinking of you and the last night we spent together. I really felt close to you Anna."

Her answer didn't come right away. "We just had dinner and played cards, Troy."

"I was thinking of what went on afterwards Baby."

She giggled. "You must have been really hard up to get your jollies from a kiss on the cheek, Troy."

"No, Baby. I meant what happened afterwards."

"Afterwards, I went to bed. That was it."

What? My mind was reeling. "You didn't come back out?"

"No, I didn't. But could you look in on Alison for me? Mom and I are out of town visiting friends and she is by herself. Please Troy."

I set there, totally stunned. If it wasn't Anna, then it could have only been her Mom or -----.

"Troy, you there?"

"The night I was at your house, was your Mom awake when you went inside?"

"Alison was the only one still up. She passed me in the hall on the way out to take a walk. Could you look in on her, Troy?"

"S---Sure, Anna. I'll do that."

Anna told me that Alison was home and then hung up. It was Alison that I made out with? I didn't know what to feel. I didn't know if I should be pissed or flattered; turned on or turned off. Being honest with myself, Alison had to be the best kisser I ever had in my arms, not to mention the blow job. But that wasn't really fair to her or me. I guess that I should call her and get this straightened out. When she answered the phone I told her that I had something to talk to her about and it was very important. She said that she was at home and would be expecting me.

On the drive over I rehearsed what I was going to say. I was going to tell her that, even though we were friends, that a romantic relationship between us wouldn't work. I tooled up the driveway and was soon at the front door. I would just have to lay it on the line to Alison. Make her see that it wouldn't work. The door started to open. I would just have to be firm and ----tell----her--- like--- it---. Judas Priest!

Alison stood in the doorway. Her coy smile wasn't the only thing that stunned me. She wore cut off jeans and a lavender blouse that showed off enough cleavage to make a bulldog break his chain. Her makeup was perfect. Smokey lavender eye shadow accentuated the most beautiful eyes I had ever seen and her lips took on the color of succulent black cherries. She looked like she just stepped out of a glamour photo shoot and It looked to me like I was in deep shit.

Alison blushed. "Hey, Troy. Nice of you to look in on me." She cupped her new breasts. "How do you like them? I am so glad I don't have to wear those fake breast forms anymore. Come on in. What was so important?"

My mouth was dry and for some reason I forgot the reason I was there in the first place. "W--Wow, Alison. You look---really---great!" We walked through the foyer and ended up in the kitchen.

"Thank you Troy. Now what was so important?" She repeated.

I would have liked to have said something that James Bond would have rattled off to get his latest conquest into the sack. I just stood there like a lovesick fool, about drool all over himself. But it was the truth though.

Alison's eyes sparkled. "You suspected it was me that you were kissing, that night." I nodded like a total idiot. She stepped forward and her scent overwhelmed me. Her arms slipped around my neck. "You wanted to see if it was true."

We were nose to nose. "I-I-I n-n-need to talk to you."

Alison huskily whispered in my ear. "What do you want to say to me, Troy?'

I swear I was about to answer. I licked my lips and then so did Alison. Her tongue slithered into my mouth and my arms circled her waist. The last of my willpower faded as she pressed herself up to me. With an incredible effort I pushed her backwards, against the wall. Alison's eyes widened, wondering what I was about to do to her. She groaned when my lips found the nape of her neck. I was lost in what I was doing as Alison ground her body into mine. Her mouth found mine again and I thought she was going to suck the life out of me.

I pulled back. "You are so damn hot Anthony......." The realization of who she use to be hit me. "No... this is wrong. We shouldn't be doing this." I reeled away and headed for the door.

"Troy!" I heard Alison cry.

I didn't care. What the fuck was I doing? Alison use to be a guy for Christ's sake. And my friend to boot. I headed for my Jeep. I slid behind the wheel and was soon backing out of the driveway. I looked up in the rearview mirror out of habit and romped on the brakes. Alison was standing there, in my way, with tears running down her cheeks.

"Move Alison!" I commanded.

"No, I won't move till you hear what I have to say Troy." She yelled in return.

"I'm warning you Ali. Get out of the way."

"You're going to have to run me over then, Troy Boy, 'cause I'm not going to budge."

I blew out a exasperated breath and turned off the ignition. This situation had got way out of hand and maybe I overreacted. But I should have never let it get this far in the first place. I don't know what I was thinking. She was so damn beautiful, that I let my dick do all the thinking for me. Then when she wouldn't let me leave, it floored me. I was so stunned that Alison could be so stubborn. Anthony was never like this. He was such a pushover that he went along with everything I said. But not Alison. I got out and she walked up to me. Her eyes were narrowed and she looked determined enough to chew steel and spit out nails.

She wagged a finger at me. "Troy Andrew Malone. Listen to me and listen well, buster." God, I couldn't help thinking how hot she looked! " And you're going to keep that trap of your's shut till I've had my say. You hear me?"

"Yes Ma'am." I squeaked.

"Good! Now listen up. My attempt at suicide turned out to be a blessing in disguise. The psychological counseling was my wake up call. Anthony, never knew where he stood or where he was going. As Alison I have learned so much about myself. I can do things that I never thought was possible before. I now have the courage to live life and not just let it pass me by."

"That's.." I started. She shushed me and continued.

"I never felt any confidence as a guy, but this transition has opened up feelings in me that I never even knew existed till now. And some of those feelings are about you. I hated it back when Anna was leading you on. She just wanted to use you and that was it. She has done it before, with other guys. But this time it was different. I was actually furious that she hurt you. The sessions with the therapist made me realize how much I really do care for you." Her head drooped a bit and she averted her eyes.

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