Danny Becomes a Sissy part 1

“What are you thinking?” Dr. Brooks asked.

Daniel realized he had been spacing out again. Well, not really spacing out – staring at Dr. Brooks’ pretty face. Daniel had never seen a doctor as beautiful as Dr. Brooks.

She was young, maybe thirty, but she looked younger. She was pale and tall, as tall as Dan and even taller in heels. She had high, round cheeks, emerald eyes and the straightest, blackest hair you can imagine, flat bangs cut across her brow and the rest pulled back in a high ponytail. She was in a tight blue skirt that reached mid-thigh and black stockings. She had been wearing a suit jacket that matched her skirt but she had taken it off and draped it on the back of her chair. She was wearing a white, buttoned blouse which was sleeveless and her toned shoulders were somehow as distracting to Dan as her legs and her face. The chunky black glasses just kicked her sexiness into porn star territory.

“Danny?”

He realized he was doing it again. His eyes were lost in the curve of her neck, wishing her blouse was a deeper cut. He blinked a couple of times to clear his head and looked at her.

“Huh?”

“What are you thinking right now?”

Dan felt his cheeks starting to get hot. No way he could tell her what he had just been thinking. Dr. Brooks thought Dan had trouble opening up to her but he just never knew what to say. Sometimes she just sat in silence to try to get him to talk but Dan was content to just stare at her thighs and pretend to space out.

“Um, nothing,” he mumbled.

The hint of a frown played at the ends of her pouty lips. “We can’t make any progress if you don’t want to open up, Danny honey.”

That was another thing. Dan had never had a doctor who called him “honey” or “sweety” or “babe.” In fact, he didn’t even go by “Danny.” Dr. Brooks had just started calling him those things. Trying to get him to open up, he guessed. She even scheduled the front desk girl to go on her break when Dan had his appointment so there was no chance of them being overheard. Dan knew it was just in his hormone-addled brain but it kind of seemed like Dr. Brooks wanted to fuck him.

“Um, sorry Doctor Brooks,” he mumbled.

“Gwen,” she corrected him with a smile.

“Right, uh, sorry Gwen.”

She laughed, hands clasped in front of her and positively beaming at him. “No need to be sorry, Danny sweety. How about this: your mother referred you to me because she was worried you were depressed. We’ve gone through all that and you don’t think you’re depressed so let me ask you: what’s troubling you? Your mother and Chris both think you seem distant lately.”

Chris was Mom’s girlfriend. Yes, girlfriend. After Dad left Mom started dating women exclusively. Pretty quickly she and Chris got together and they all moved in together. Dan decided to just say it out loud.

“It’s Chris,” he blurted out.

Dr. Brooks raised her eyebrows slightly but remained silent. Dan fidgeted in his chair. Suddenly he didn’t feel like “just saying it” anymore. He didn’t like asserting himself or drawing attention. Speaking tended to draw attention. He noticed he could just barely see the crease between Dr. Brooks’ pinky toe and the next one with the way her shoes were cut. He wondered if her toe nails were painted.

“What is it about Chris, honey?” she asked gently, lifting her chair a little so she could scoot closer.

He sighed. “It’s just…since she moved in…it’s like Mom’s not my mom anymore. She’s Chris’ girlfriend. They spend all the time together and even if Mom’s hanging out with me Chris is there too and she moved all her stuff into the house and the playroom turned into her home gym.”

There was a pause before either of them spoke. Dr. Brooks started to say well, sweety when Dan cut her off.

“And she wrestles me.”

“What?”

“She wrestles me. Like roughhousing but she’s really strong.”

“Right, I believe she’s a mixed martial arts fighter in her spare time, right?”

“Yeah, so she’s like really strong and good at wrestling. She thinks I like roughhousing but I don’t and she doesn’t believe me. Sometimes she’s…” he hesitated. “Sometimes she’s pinning me down and she tickles me or puts me in a weird hold or something.”

“Sweety, that’s-“

“I know she’s just playing like I know she’s not trying to be mean but she doesn’t believe me when I say I wanna stop.”

“Danny, that’s fantastic.”

“That’s…huh?”

“This is perfect- Okay, I’m getting ahead of myself. Daniel, I remember you said you had some issues sharing space when your cousin came to visit. I think we can come up with some strategies that will be very useful when you go off to college. Now, with the wrestling issue: wrestle her back!”

“But…I don’t wanna-“

“Daniel,” she said, and he was taken aback at how softly she said it. Dan couldn’t tell if his mind was playing tricks on him or if her pupils had just gotten bigger and her cheeks a little redder. He crossed his legs to hide the erection that was growing.

She sighed and took off her glasses and set them aside. She leaned forward and took one of his hands in her own. Dan had no idea what to say.

“You know I’m not a very traditional therapist, right?”

He nodded. His mom had made sure to emphasize that to him beforehand for some reason.

“Some of the things I say are going to seem very strange or unusual. Stuff that most therapists don’t say, because I know it works. I want you to at least try the things I suggest, even if they seem strange or un-traditional. Can I have your commitment on that?”

She was stroking the back of his hand with her thumb. Dan’s dick was straining painfully against his jeans. He just gulped and nodded.

“Good,” she whispered. She sat up a little straighter but held onto his hand.

“Now, Danny, I’m going to tell you something I don’t think a traditional therapist would tell you: you’re kind of a wimp.”

Dan blinked in surprise. Dr. Brooks held onto his hand a little tighter like she were afraid he would try to flee.

“Your dad never roughhoused with you in a positive way. He set a terrible example of masculinity for you so you rejected it. Because you’re a sweetheart and you would never treat a woman the way he treated your mom. The problem is, especially with your mom bringing all these women around, her girlfriends and your aunt and your cousin, you’re not being socialized to become a man. You’re becoming more feminine. I’ve seen it, even since we started our sessions.”

Dan had no idea what she was talking about. He dressed like a dude. Talked like a dude. He just didn’t like conflict.

“You’re not assertive, you’re not physical, you don’t know how to fight back,” she continued. “This is great, what Chris is doing. I think she wants to see that in you. You should fight back.”

“She’s stronger than me…”

“Maybe. You’re bigger than her. And how do you know she’s stronger? Have you really tried to overpower her?”

“I guess…not…”

“Do it. Get mean. Don’t worry about whether you’re hurting her. Ask her to show you a move and then do it on her and don’t let her up. Show her who’s boss. Make her uncomfortable for making you uncomfortable. Get on top of her and tickle her back. Stick your hand in her shirt. Slap her tit,” she laughed. “I’m kidding,” she said and raised her eyebrows a little and paused in an I’m-not-kidding expression. “If you really want to surprise her come at her first. Wait until your mom’s not home and grab her in the kitchen and bear hug her and don’t let go. See what I’m saying?”

Danny hesitated. She was right about one thing – this didn’t seem like something a therapist would say.

“I don’t know…”

“Daniel, you said you would try. It’s really important you try to do this. I mean it.”

He scratched his head. “Well, okay.”

She leaned forward and hugged him. He was lucky she didn’t tell him to stand up for their hug because he would have came in his pants. As it was, just their shoulders were touching and his dick was pulsing painfully against his pants. She kissed his cheek and finally sat back and released him.

“I’m really proud of you, sweety. It takes a lot of courage to change. I have every confidence in you.”

—————————————

“So, Danny, how did it go?”

“Er, not so good.”

“Why not?”

Dan felt his cheeks getting warm. “It just, um, didn’t.”

Dr. Brooks crossed her legs and folded her hands in her lap. “Well, tell me what happened.”

“Um, I tried to do what you said…I asked her to show me a move and she seemed really happy. It’s like a transition where they’re trying to choke you but then you get on top of them. She showed me it and then I did it on her and I was trying to do what you said, like, I was on top of her and I didn’t let her up and I tickled her-“

“Under the clothes or over the clothes?”

“Um, over the clothes I guess. Her ribs.”

“Hmm.”

An awkward pause before she said, “Well, continue.”

“And then…this is embarrassing,” he mumbled.

“That’s okay, honey. It’s important you tell me so we can make progress.”

“And then…I, like, gave her a raspberry on her neck she was giggling a lot and I kind of…got hard.”

“Okay, that’s natural. So what next? Sounds like it was going just fine.”

He rubbed the back of his neck. “Well I kind of backed off so my boner wasn’t rubbing on her and she pushed me off balance and then she got on top and tickled me for a long time. She kind of…squeezed my boner through my jeans a few times while she was making fun of me.”

“Good!” Dr. Brooks said. Was that annoyance he heard in her voice? She sighed and pinched the bridge of her nose. “Okay, that’s actually progress, believe it or not.” She took off her glasses and set them aside. “Here’s what I want you to do. Stand up.”

Dan stood up. So did Dr. Brooks. She was wearing flats today so their faces were level. She held her arms out.

“Hug me.”

She was dressed similarly to last time, black skirt and a white blouse that was more open-throated than the other one, long-sleeved with shoulder cutouts, silky and so thin that it would be like touching her skin directly if he put his hands on her. Dan coughed and sat back down to try to hide the erection forming.

“Daniel,” she said in clipped, clinical tones, like this was something she had explained many times before, “I know what your issue is, and I know why you’re sitting down right now. I know what you’re trying to hide. Don’t hide it. Stop worrying and stand up and hug me.” She shook her arms a little for emphasis and smiled. “Plus, I know you want to,” she said with a wink.

She had to insist several more times but eventually Dan gave in and stood up, hobbling over to her as his dick strained against his pants. She held still, waiting for him to initiate the hug so he did, awkwardly placing his hands on her back and pressing their shoulders together. She threw her arms around his neck and pressed their bodies together. His dick pressed against her thigh and he backed his hips away reflexively.

“Don’t do that,” she said firmly, pressing their hips together again. He started sweating. She squeezed him against her a little tighter and he wrapped his arms around her all the way. Her back was smooth and soft but toned. Her thighs were firm against his and he could feel the swells of her breasts against his chest. She nuzzled her head next to his, resting her chin on his shoulder. It was amazing. He felt like he was soaring through the universe. He felt so nervous he might have a heart attack but he didn’t want it to stop. He wasn’t even sure how long it lasted. It could have been ten seconds or ten minutes. Eventually she released him and he wobbled to his chair. He was dizzy with excitement.

“See? You can do it. How did that feel?”

“Good,” he mumbled.

“What I want you to take away from today is this: get mean. You didn’t get mean. You were playing. I want you to use your mother’s girlfriend to make yourself feel good like that. Wouldn’t you like to feel like this again?”

He nodded and said yes.

“Good.”

————————————-

“So, Danny honey, how did it go?”

“Not…not so good. Bad, actually.”

“How so?”

Dan fidgeted and stared at her feet, refusing to make eye contact. “Are you sure this is the best, um, strategy?”

“Yes, I am. Why? What happened?”

Dan had been trying Dr. Brooks’ strategy for about ten sessions now, a few months. He had taken her advice and it seemed to be working. He originally wanted the wrestling sessions to stop but instead his attitude had shifted. He had gotten in better shape over the last couple months and he got better at grappling, learning new techniques and learning how to use his weight to his advantage.

He got “mean,” too. He’d pin Chris down and not let her up, tickle her under her shirt or tickle her butt by shoving his hand up her shorts. He ground his boner on her butt and she would giggle hysterically like it was a joke. He would put her in a rear naked choke so hard until she tapped out and he would let her catch her breath and then do it again. The meaner he got with her, the nicer she would be to him next time she got on top. It was working.

Until this past week. Something had changed.

“Do you have to, you know, call the police like if something bad happened?”

“No, I don’t.”

“Oh…aren’t you, like…isn’t it called a mandatory reporter or something?”

“Ah, that. I told you, I’m very non-traditional. How can I help my patients if I call the authorities on them?” She paused, her face and chest getting slightly flushed. “Did you…penetrate Chris or something?”

“No, not me-“

“Oh.” She looked disappointed.

“-it was something she did. Er, something she does.”

“What’s that, honey?”

“It’s really embarrassing…”

“Good. We make the most progress whenever something embarrassing happens between you and Chris. What happened?”

He didn’t want to tell her. He tried to change the subject a few times, tried to clam up, tried to say he would just tell her later, but she didn’t relent until he finally gave in and told her. They had been wrestling, just like normal, and Dan ground himself on her butt for a little too long and came in his pants.

“Understandably. But this isn’t the first time that’s happened, correct?”

“Right, but…I think she didn’t notice before and she noticed this time.”

“How did she react?”

“She seemed weird…like a really intense look like I couldn’t tell if she was angry or happy…and then she did some stuff to me.”

“What did she do?”

“She got some stuff from Mom’s room…like BDSM stuff. She handcuffed me and then tied my legs and then she got the cuffs around the leg of the sofa so I had to lie down on the carpet…she kind of…got naked and smooshed her butt in my face. A lot. So much I couldn’t breathe and then she would let me breathe and then sat on my face a lot. For like an hour. I think she…you know…”

“Climaxed? That seems fair, don’t you think?”

“…huh?”

“Well, think of it as an extension of the game you’ve already been playing. I mean, it’s been all about power from the start, hasn’t it? You used your body to restrain her and you used her for sexual release. She did the same thing to you; she just isn’t strong enough to do it without tools. Anyway, you said this has been ongoing. Obviously you didn’t just let her handcuff you the next time, correct?”

“She’s really sneaky,” Dan mumbled. Dr. Brooks just laughed so he continued, “Plus, like one time I had her pinned down and she humped herself on my thigh until she…climaxed.”

“Honestly, Danny honey, you have two options at this point. One: let her take control back from you and lay back and enjoy it, because let’s face it…”

She let the implication hang.

“Isn’t this kind of too far?”

“How so?”

“Isn’t this, like, cheating on Mom?”

“Not at all. Your mother’s perfectly aware of how I operate.”

“With…her girlfriend?”

“Fine, we can involve your mother more directly to avoid confusion. I’ll talk to her when she comes to pick you up. Now, two: you can take control back yourself. Get mean. Meaner.”

“I thought I was…”

“Come on, now, sweety. Tickling? Wedgies? That’s kid stuff. That was to build your confidence. Smack her up. Scare her. Drag her around by her hair and throw her on your bed. Don’t jizz your pants; jerk off on her. Be a man. Or else.”

“…or else…?”

Dr. Brook sighed and tossed her glasses aside again. It was a gesture Dan was starting to dread.

“Stand up,” she told him. They both stood up. “Hit me,” she said.

“What??”

“Hit me. In the stomach. I can take it,” she said, patting her belly. Judging from the solid thumping sound she had some real abs under there.

“No!” he protested. He steeled himself internally. This was totally crazy. He would never hit Dr. Brooks.

“Fine,” she said. She balled her right hand into a fist and sunk it into Dan’s gut. It knocked the wind out of him and he doubled over, arms crossed across his belly and falling to the ground. She knelt down next to him, grabbed his wrist and moved it out of the way and hammered his ribs repeatedly, whap, whap, whap, whap, whapwhapwhapwapwhap.

“Ready to hit me now?”

“No,” he wheezed. He knew this game, from his dad. If he hit back it would just make his punishment worse. He couldn’t hit Dad because he was too big; he would ultimately win no matter what so he had to just take it.

“I know what you’re thinking. I can see it in your face. I’m not your dad. I don’t hate you. I’m your therapist. I’m your friend and frankly, I love you more than your dad ever could. You made a commitment to at least try and right now you’re not trying. I know you’re perfectly capable. Now, hit me.”

“No,” he pouted.

“Fine,” she said and got up. She sounded actually angry now. Dan felt terrible for disappointing her but she was asking him to do the impossible. If he could stand to get hit from someone who hated him then he could stand to get hit by someone who loves him.

“Put this on,” she said. She pulled something out of one of her desk drawers and tossed it on him. It was a sundress. Black with a pink and white floral pattern.

“Wha…?”

“If you’re going to be a sissy then dress like one. Go ahead. Go ahead.”

“You know what?” he snapped. Whatever, he decided, let’s play this game. He got up and pulled his shirt off over his head and pulled his jeans down and stepped out of his shoes. In just his boxers and socks, he put the stupid dress on.

Dr. Brooks rounded the desk, a pair of handcuffs in her hand and suddenly she was on him, hauling him around and handcuffing face-down him to the leg of her desk. She pulled the dress up around his hips and yanked his boxers off. Dan was about to protest when he looked and saw Dr. Brooks was stripping. She unzipped her skirt and let it drop and pulled her stockings and panties completely off. Dan gaped at her. Her pubes were trimmed in a triangle above her pussy. Her hips and thighs were more toned than he would have thought, which was extremely sexy to him. She pulled her top off and unclasped her bra and tossed it on the ground. She had abs and perky, round breasts with pink nipples.

Dan wasn’t sure what kind of punishment this was supposed to be. She was right, he did enjoy when Chris rode him until she climaxed. He was just conflicted about it. He wasn’t conflicted about Dr. Brooks riding him. She could ride his cock, his face, she could do whatever she wanted. He was just facing the wrong direction. It wasn’t until she did something behind him, some rummaging in a drawer and some buckles being fastened, it wasn’t until she straddled his butt and he felt something cold and wet pressing against his butthole that he realized what was happening. She was trying to fuck him with a strap-on.

“Whoa, wait a minute.”

She leaned down so their faces were almost touching. “You have a change of heart? Ready to take charge?”

“Well, no,” he said and then he grunted as he head of the dildo slid up into his ass.

“Oh, stop whining. It’s a small one,” she told him, slowly inserting more and more of it into him until her hips were pressed against his butt. She laid on his back and scooped her arms under his shoulders and grabbed them firmly.

“You’re at a very crucial point in this process, Danny,” she grunted, slowly pulling almost all the way out and gently shoving the whole thing back in. “You need to make a real decision. Are you going to be a sissy or a man? I’m going to treat you like the former until you convince me otherwise and guess what? So is Chris and so is your mom now. You can just be a sissy forever, or,” she grunted again, speeding up the pace, slapping her hips against Dan’s butt and making it jiggle, “you can be a man. Up to you.”

She reached under him, groping for his cock.

“Lift your hips up,” she whispered. “Lift them up so I can see what you’re working with.”

Her fingers brushed against the his balls and he lifted his hips instantly to give her access. Still fucking him, she stroked his cock, gently running her fingers over the head of it again and again.

“Oh shit,” he said, cheek squished against the carpet.

He felt the orgasm coming from inside his hips, past where Dr. Brooks’ plastic dick was fucking him and it made the sensation even better as it shot out of him, spurting against her fingers as she continued pleasuring him.

“That’s good, baby,” she whispered and kept going as his cock twitched and spurted. Finally he finished and she stopped.

“I’m really stacking the deck against you here, Danny, because I believe in you. Positive reinforcement for your sissy behavior is going to make it even harder but you’ll come out the other side even more of a man. Or not, I guess.”

She pulled out and cleaned them up with a towel. After she uncuffed him she made him lie with his head in her lap and she put a cold compress on his ribs where she had hit him. She stroked his hair with the other hand as he just looked up at her inscrutably.

“Um, Doctor Brooks?”

“Call me Gwen, Danny,” she reminded him, wiping a stray eyelash off his face.

“Does…this really work?”

“Like I said, honey, it really goes one of two ways. I understand the appeal of being, you know, a submissive man but did you notice something?”

Dan’s eyebrows drew closer together. “What?”

“You climaxed and I didn’t. I can’t really get off unless it’s with a man who knows what he wants,” she sighed. “It’s fine. The choice really is yours. I just want to make sure…”

She kept talking but the first comment had clearly set the gears turning in Dan’s mind.

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