tagTranssexuals & CrossdressersAlex to Alice Ch. 01

Alex to Alice Ch. 01


Everything had started off simple enough for Alex. He had met Elena at a bookstore while he was researching for a college paper. She was quite the vision at 29. She stood a respectable 5' 8" with a voluptuous body. While slightly plump, she maintained her hourglass figure and filled out quite nicely. Her straight blonde hair flowed down to her well-shaped ass. He couldn't help but stand in awe at her beauty when they had bumped into each other.

Alex on the other hand, at 24, was a mess simply put. Standing at 6 foot even, he was skinny and had shaggy brown hair. Obviously, he was a victim of the early 90's rock scene.

Her smile was his undoing as he gazed into her gorgeous green eyes. She had picked up on his nervousness and began with small talk. With what started as a few pleasantries, it eventually grew into sharing their life experiences until they realized it was closing time. Elena invited him back to her place for coffee and from that night on they were inseparable.


After a several months of dating, and them even moving in together, Alex began noticing Elena withdrawing herself from him just slightly. Concerned with this he had made her a romantic dinner one evening to try and show her how much he cared. She received it with a smile and a kiss on his cheek.

"You seemed so overworked. I decided that I would try to ease your mind a little and make you a special evening." He motioned for her to sit down as he pulled the chair back for her.

She smiled again, "you really didn't have to hun." Sitting down slowly at the table she looked at the great meal he had prepared. "This really wasn't necessary."

Carefully pushing in her chair, he sat down and motioned for her to eat. "Sure it was. You've seemed distant lately, even when we have sex. I've just been worried that maybe I did something wrong."

"No! It's not you, really." Looking at him sympathetically she said lightly, "It's just me. I've been working a lot and I didn't want to trouble you because I know you're working hard at graduating this year."

"If that's the truth, then don't worry about it. I took all my difficult classes during the first semester this year. My last few classes will be a breeze, so if there's anything I can do to help you just let me know. Ok?"

She smiled, "I'll keep that in mind." The rest of the night went smoothly and that night they had the best sex they have had in weeks.

Several days had gone by and Elena returned home humming a very happy tune. Alex looked up from his homework and smiled at her, "You seem to be in a great mood today! What's the occasion?"

She sat down next to him and handed him a CD, "This is what I'm in a great mood about."

He looked it over carefully, but it was just an unlabeled CD in a blank case. "So what is it? An illegal copy of an upcoming album?"

Giggling she replied, "No, but good guess. It's something I've wanted to try. It's a music CD that you're supposed to listen to while you sleep. It's supposed to increase sexual pleasure."

He looked at her skeptically, "It sounds like a load of crap to me. I thought you were rather enjoying sex the past couple weeks."

"I have been, but it's just something to try. Plus it may help you relax more while you sleep so you can do better in school. I know you've only got easy classes, but you still need your rest!"

Taking a deep breath, he considered it for a moment. What could it hurt? "I suppose I can try it for a night or two. But, if it doesn't seem like it's helping or it interferes with my sleep I'm going to stop. Is that ok?"

She leaned in and kissed him, "As long as you're willing to at least give it a try that's fine by me."

That night he put the CD in and put on his headphones. Light soothing music flooded into his ears. It didn't seem like anything special, but if it made her happy he didn't really care. She obviously wanted to spice things up and he enjoyed pleasing her. She had always more than satisfied him and he wanted to return the favor. After a few moments he dozed off.

The next day at breakfast Elena asked, "How did you sleep?"

"Eh, not too bad. I really don't feel any different but it didn't keep me up so I guess I can deal with it for a while to see if it helps spice things up."

"I'm glad." She sipped on her coffee as she peered into his eyes. "I just want to see if it works."

For the next week he listened to it before he went to sleep and he hadn't noticed any change. Granted, with there busy schedules they hadn't had time to become intimate at all. But still, he carried out her wishes.

Finally, one Saturday night, she greeted him half naked to their bedroom. She stood in the doorway wearing a sexy red corset and thong. "I want to try something babe." He stood there in awe at this vision. "I want you to take a shower and use the soaps I've left out for you. Take your time, as I want you to be relaxed for tonight."

He smiled devilishly, "I don't think I'll be able to take my time knowing what's coming."

Placing her pointer finger over his lips she whispered, "Take about 20 minutes to yourself baby. Trust me, this is worth the wait."

With that, he went in and began showering. The soaps smelled of exotic fruits, which he didn't mind. He assumed these were some form of aphrodisiacs. As he cleaned himself off he felt his skin tingle and began noticing his body hair rinsing off. He had always kept his chest and stomach shaved, but this was a little new.

When he returned to the bedroom he found her lying seductively on the bed. The room smelled of intoxicating incense, flooding his senses. Candles were meticulously placed all around the room to help create the atmosphere. She beckoned to him silently with her finger.

Obediently he crawled onto the bed and between her legs feeling his body pressing into hers. She smiled at him lovingly and they shared a deep kiss. Their tongues danced in each others mouths feverishly. After a moment he began kissing her neck and nibbling softly. Light moans escaped her lips between kisses. Her fingers dug into his back with each soft sensation of his lips on her petite neck. His mouth finally making it's way to her pert nipples, taking the first one in and kissing it. Teasing it ever so carefully with his tongue making her breath quicken. His hand moved over her smooth thighs, caressing every inch, as he made his way to her wet pussy. As he teased her nipple with his mouth, his hand made it's way to her clit. Touching it softly and rubbing her lips, making her moan even more loudly.

She could feel her body betray her as she craved his touch. Feeling his fingers move around her hot pussy ever so carefully, she moaned even louder as a finger slipped in. He could feel the muscle tense around his finger, pushing more of her love juices out. His cock throbbed in envy of that finger. Sliding it in and out, he slipped in a second finger as he continued to tease her breasts and neck with his mouth. Her eager pussy began to give way to pleasure and ecstasy, as she felt the wave of her first orgasm approach. It'd had been too long since she had last had his touch. Her body ached as her muscles began to spasm and her back arched. She dug her nails deep as the waves of pleasure came over her.

After a moment she regained her composure and began stroking his rock hard cock. She kissed him madly, wanting it inside her so badly. She pushed him on his back and began kissing the tip of his cock teasingly. She looked deeply into his eyes as she licked at the shaft and began to take his throbbing member into her wanting mouth. Alex could feel himself going deep into her throat; she always made him feel so good. After a moment, she began moving a hand down his inner thigh towards his ass. Too distracted by her sweet lips he failed to notice the hand creeping towards his ass. She pressed her finger against his virgin hole and rubbed around it teasingly. He moaned sharply as her finger began to violate him. Part of him wanted to rebel, but it felt right. Something inside of him wanted it. Her finger pushed through into his asshole and she pumped it in and out slowly at first, until it matched rhythm with her mouth on his cock. She could tell he enjoyed it, his cock was hardening still. His body was betraying him as he felt his muscles begin to spasm and he blew his load in glorious orgasm.

Elena moved back up to him, after swallowing and licking him clean, "Did you like that?"

He panted lightly, "Yes I did. It was different, but it was good."

"I'm glad." She laid her head on his chest and they drifted off together. The next morning he woke up alone laying in the bed still swimming in the events of the night before. He wasn't sure where it came from, but it felt great. Elena walked into the room and scoffed at him, "Still in bed you lazy bum? We have things to do today, but I have a request. I want you to wear these." She threw a pair of black silk panties at him. "Don't question it, just trust me and do it pet and we'll both be happy later."

Not really sure what she had planned he just went along with it. The panties felt so slick against his cock. He couldn't help but be aroused while wearing them. It was such a foreign feeling to him. Even after getting fully dressed his newly bald body and the panties sent chills up and down his spine, it was so strangely erotic.

To his surprise the rest of the day was fairly uneventful. They went grocery shopping and had lunch in the park. Later that night all they did was sit together and watch TV. When it finally came time to sleep, she asked him to keep wearing the panties. She explained that it brought out his ass and made his bulge more appealing. Wanting to please her, he complied. He put on his headphones and drifted off to sleep. This continued on for sometime, gradually building up to him wearing stockings and a b-cup bra under his clothes. Elena had even begun corset training him to give him a shapelier figure. Eventually all of his male underwear was thrown away and replaced with panties. She had assured him that it would stay between them and if he didn't like it, she would never ask him to do it again. But oddly enough he complied. It was so erotic and dangerous. Shortly after that, she began to even doll him up in make up while they were home to make him even more feminine. In short glances he looked just like a woman at this point. She had even had him take better care of his hair and grow it out.

One night before bed she looked at him seriously and said, "I think it's time we have a talk. I've enjoyed what we've been doing, but I need more of a commitment from you. I want to make sure that you're in this 100%."

Worried that she may break up with him he quickly assured her, "I love you, and I'm 1,000% in this. Anything you need me to do to prove this I will do!"

She smiled wickedly, "Then I want you to start wearing this." She held up a male chastity device. "It will be proof that your cock and you are mine."

"If that's what you need to re-assure you, then I will do it." He felt himself slip from control with those words. He wanted to rebel, but it felt right to submit to her will.

Her hands moved quickly and she locked it on his cock. It arched his cock facing down and prevented his dick from hardening. "From now on you will pee like a woman to show your submission to me. I am your Mistress and you are my slave girl. Is that understood?"

The words struck him harshly, yet once again it felt right. "Yes Mistress."

"You have so much potential my dear Alice. Your body is frail like a woman's body and it's time we reflect that even more." The name echoed in his skull. It brought out a familiar feeling that was lost at some point. "Are you going to be good for me Alice? Are you going to obey all of your Mistress' commands?"

Once again she felt that feeling and a piece of her drifted away. "Yes Mistress, I want to be a good girl. Anything to please you." The only shred of her masculinity remaining was now locked in a tiny cage between her legs.

"Then what is your name slave?"

She took a deep breath, "It is Alice, Mistress."

Elena smiled wickedly. Her hypnosis had worked successfully. She had turned her sissy boy Alex into a submissive, sissy slave girl named Alice. She stood up and moved away from the bed, and began rummaging through a drawer. Alice lay on the bed patiently waiting for her Mistress. Elena turned around donning an 8-inch strap on around her shapely pelvis. "Do you know what slave girls do my dear Alice?"

Alice stared blankly for a moment and then almost mechanically spoke, "They suck Mistress' cock."

"Good. Now crawl over here and suck me off slave." Alice crawled off the bed and across the floor on her hands and knees. She strode carefully as not to leave runs in her stockings. Finally kneeling before Mistress Elena, Alice began to stroke her big cock and take it into her mouth. "Oh my, you're so good at this slave! I'm surprised I didn't do this sooner. I wasn't sure if you would make a pretty slave girl or not, but you have surpassed my expectations little Alice." Alice felt a little more light headed as she heard her Mistress' words, the more she spoke the more feverishly she sucked her cock. "Don't worry Alice, I'll let you finish school off as a boy with a locked clitty between his legs. But after that, you will be my slave girl. I've already ruined your little mind sweet Alice. The more you hear your name, the deeper you will fall into the trap I've laid for you. Alice and slave are your hypnotic triggers; they make you my submissive little slave girl. But you don't care. As long as you have a cock in your mouth, and soon to be your ass, you won't care. Oh sweet little Alice, I'm going to enjoy stripping away what's left of that pathetic Alex. Don't worry though; I'm going to leave that pathetic prick between your legs as a reminder. If only you had noticed I didn't date boys before you, you wouldn't have become my little subby slave girl." Alice sucked away at Elena's cock. The words being spoken echoed almost unheard through her head. She didn't care. Mistress had such a happy look on her face as she sucked her cock. That's all that mattered to her. Alice did her best to take all 8 inches of Mistress' cock into her mouth and throat, pleasing Elena even further.

Elena grabbed her by the back of her hair and pushed her face all the way down on her cock. Alice's nose was pushing into her pelvis, and she could feel the thick cock blocking her airway as it filled her throat. She started to choke and the room began to spin hastily. When she awoke she was on her knees, her head pushed to the bed and ass sticking up. Alice tried to move but found herself bound tightly. Mistress stood behind her giggling, "Well, well. It seems we're going to have to work on your deep throating more little Alice. But for now, I'm going to pop your cherry. I find it appropriate that you were my first real cock, that I should be your first cock." She stroked and lubed up her cock with her right hand as she began pumping a lubed finger into Alice's little hole. Alice moaned uncontrollably into her gag. She could feel the sensations trickling up her spine. She wanted Mistress' cock so badly, she wanted to be filled and tormented by that cock.

Elena pulled her finger out slowly and smiled. In a teasing fashion, she pushed her thick cock slowly into Alice's ass stopping at every inch to let her muscles relax around the new phallus being inserted into her virgin ass. She didn't want to break her slave girl just yet. Alice winced as she felt herself being filled by this new fat cock. Only muffled moans could escape from behind the ball gag shoved into her mouth. The cock stopped for a moment after all 8 inches were inserted. Elena ran her hands down the corseted body of little Alice as she let her adjust for a moment.

Without warning the cock began to pump in and out slowly, sending new sensations through Alice. Alice moaned louder through her gag in pleasure. Anything left of her masculinity was now gone. Memories of being Alex were fading. She no longer longed to put her little clit inside her Mistress, she wanted Mistress' fat cock in her ass. Elena smiled as she watched Alice's eyes roll back from the pleasure she was giving her. She began pumping faster and harder to truly break her. After a short while Alice felt herself loosing control and the waves of an orgasm building up slowly. Her clit throbbed within its metal prison. Finally, she let out a loud moan and began to orgasm. Her clitty shot out cum all over the bed. Elena continued to fuck her harder. She knew that this was sealing her fate. This is what made Alice her slave girl. After another few thrusts, Elena pulled out slowly leaving Alice open and gaping. Mistress once again returned to the drawer and this time returned with a plug and pushed it into Alice's sore little ass. Once satisfied that the muscles had closed around it, she moved around and ungagged Alice. "Look at the mess you made slave. Clean it up with your tongue." Elena grabbed Alice by the hair and guided her to the cum on the sheets. Alice leaned down and licked up all of the cum she had sprayed onto the bed. This time, nothing rebelled. It was right because Mistress had ordered it. That was the only thing that mattered anymore. "Good girl. From now on, you will clean up and cum messes left. Understood slave?"

Alice licked her lips clean, "Yes Mistress."

Elena petted her gently, "Open wide slave." Alice opened her mouth and Elena put something on her tongue. "Now swallow." Once again she obeyed and swallowed. "Good girl. I will leave a bottle of these in the bathroom, you will take these once a day. They will help you grow nice little breasts so we wont have to use these silly breast forms anymore. I want you to know how it feels to have sensitive tits. Now open up again." Alice complied again silently unaware her fate. Elena pushed a cock gag into her mouth this time. The tip just barely touching the back of her throat, Alice felt comfort in being completely filled from all holes. Mistress began leading her off of the bed and to a cage in the closet. "This is were slut slaves belong. I will unlock the cage and your restraints in the morning. I will have instructions for you upon waking, until then enjoy what happened tonight slave."

Alice moved into the cage and laid down like a dog. Mistress locked the cage with a padlock and put a blanket over the top of it. "Good night slave. You have quite the day ahead of you little Alice." The closet door was shut and Alice reveled in how she had pleased Mistress today. She only hoped that she could continue to please Mistress Elena so. Alice finally fell to sleep despite her full ass making her clit throb against it's tiny cage.

Report Story

byblasphemy_mixtur21© 4 comments/ 97758 views/ 21 favorites

Share the love

Also in this series

Tags For This Story

Report a Bug

1 Pages:1

Please Rate This Submission:

Please Rate This Submission:

  • 1
  • 2
  • 3
  • 4
  • 5
Please wait
Favorite Author Favorite Story

heartxxfreakxx, Ultimak and 19 other people favorited this story! 

by Anonymous

If the above comment contains any ads, links, or breaks Literotica rules, please report it.

There are no recent comments (4 older comments) - Click here to add a comment to this story or Show more comments or Read All User Comments (4)

Add a

Post a public comment on this submission (click here to send private anonymous feedback to the author instead).

Post comment as (click to select):

Refresh ImageYou may also listen to a recording of the characters.

Preview comment

Forgot your password?

Please wait

Change picture

Your current user avatar, all sizes:

Default size User Picture  Medium size User Picture  Small size User Picture  Tiny size User Picture

You have a new user avatar waiting for moderation.

Select new user avatar: