Sexual Conundrum

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I get help when questioning my sexual identity.
7.1k words
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18.6k
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Part 1 of the 2 part series

Updated 07/12/2024
Created 06/21/2024
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I'm quite certain that some of you reading this, like me, have questioned your sexual orientation. Why do we enjoy taking a nice hard cock between our lips while at the same time wishing we could satisfy the women in our lives? We don't think of ourselves as gay, but we don't act 100% straight 100% of the time either.

I had to get some answers. I was so confused. I had so many questions. Am I gay? If not, why then do I become aroused seeing Tom's cock? Why is it that I get so turned on sucking it? Why do I look forward with great anticipation to his visits when I know he's coming over to fuck my wife and have me suck his cock?

All those questions kept running through my mind. My wife and Tom have both called me cock sucker, faggot, homo, and other names that should have insulted me. Instead, as I slovenly worshiped Tom's big cock while those names were raining down on me, they only served to excite me further.

I needed counseling, answers to my questions. I needed an expert. I made an appointment with a psychologist who, after I explained my issues, he adjusted his cock through his trousers and suggested I go elsewhere. "Son, I'm just not the right person to answer your questions. You'd be better off with someone who specializes in dysphoria.

Walking me to the door, he patted my big bottom and mentioned that he wouldn't mind spending some quality time with me. "On a nonprofessional level, of course," he smiled.

"Um, well, maybe," I said trying to be polite. "Thank you for your time, doctor."

I went back to searching. I found a Dr. who said she could help me.

It wasn't so much excitement that I felt as I drove to my appointment but the angst of having to relate my situation again to another stranger.

"You must be johnnie," Dr. Martin said, coming around her desk. "I'm doctor Martin. Now before we begin, you need to know that I'm unlicensed. And to be perfectly honest, johnnie, I'm not a PHD. I am however educated in the how, why, and ways of sex. With that said, if you decide to use my services, you may call me doctor and I shall call you johnnie or whatever else I choose."

"Pleased to meet you, doctor," I smiled. She handed me some forms and asked me to fill them out. I answered each question. Every question addressed my sexual preferences, experiences, and fantasies, and fears.

She seemed pleasant enough. I had no problem opening up to her. I told her what was going on at home and the questions I had about my own sexuality.

Dr. Martin took notes and occasionally smiled at something I said.

When I at last finished explaining why I was there, Dr. Martin put her note book on her lap. "You say that this Tom fellow has a very nice, your words, cock."

"Yes, ma'am."

"And you achieve an erection thinking about his visits, knowing you'll be kneeling before this man, sucking his cock?"

Sigh.... "Yes, Dr. That's all true."

"Have you ever wanted to take your rightful place and instead of Tom, it's you having intercourse with your wife?"

I blushed. "Well, sometimes but Tom does it so much better than I ever could."

"Do you watch them?"

"Oh yes, ma'am," I enthused. "All the time if Tom feels my behavior earned me that reward."

I saw a look of recognition cross Dr. Martin's face.

"Do you know what's wrong with me?" I asked, hoping she did.

"I have some ideas, johnnie. Let's not rush things. We need to explore the depths of your sexuality a bit further."

I apologized to which she made note of on her pad.

"You seem to have a natural desire to please people, johnnie. Tell me. Have you always been like that?"

I explained to Dr. Martin that considering my build, that I was a timid sort. "I have never challenged anyone, Dr. I have never been considered a threat. So, yes, I guess. I've always wanted to please those in my orbit."

More scribbling on her pad. "Now you may think what I'm going to ask you to do is strange, but I assure johnnie, it's part of me delving in those questions you have about yourself."

"I understand, Dr. Martin."

She had me stand up so she could appraise my body, my stature.

Dr. Martin copied down her observations, saying each one as she quickly made her notes. "Not tall, narrow shoulders, slim waist, hips a bit wider than most males. Subject has nicely rounded buttocks, his best feature."

"You may sit now, johnnie."

"Thank you, Dr."

"Now I have some idea but I'd like to consult with another professional. Can you come back same day, same time next week?"

"Yes, ma'am," I said standing up to leave.

I spent a hopeful week that Dr. Martin could explain away my uncertainties, my insecurities.

I thought a lot about her during that long week. She was a pretty woman. Cute but not beautiful. I noticed she was fairly flat chested. She was a tad taller than me and wore flats. I liked her smile. Her eyes looked upon me kindly without judgement. She listened to my concerns with empathy. I felt I could trust Dr. Martin and decided I liked her.

With great anticipation, I rode the elevator up the Dr. Martin's office. There was no one in the waiting room which I later learned that was protocol. Patients were never to meet. It was more a privacy issue for those of us wanting help.

I figured the doctor had an alarm in her office that let her know when a patient entered the waiting area.

"johnnie, right on time. How are you?"

"I'm fine Dr. Martin. And you?"

When I was seated, Dr. Martin explained that she'd spoken with some of her colleagues and they recommended a test. "It's an easy test, johnnie. No need to have studied," she giggled. "This is a recognition or preference selection that may go a long way to answering your questions."

"What do I have to do?" I asked, anxious to get on with it.

"Easy, baby boy. Let me explain first."

Hearing her call me baby boy made my tummy quiver with butterflies. But in a nice way.

She went to her desk and picked up a magazine of sorts. I noticed her nicely rounded bottom and felt guilty when my dick twitched.

Apologizing that it was not computerized, she handed me what she called a portfolio. Sitting beside me, my dick grew to its full 4 1/2" when I felt her thigh against mine.

I shifted in my seat hoping my erection wasn't noticeable. "Now this is what I want you to do. On each page you'll see contrasting pictures. By contrasting, I mean both will be similar but with some differences. You will tell me which you like, or identify with, or prefer. Each picture will be labeled A and B. You tell me if you pick A or B. Do you understand?"

"Yes, ma'am."

I knew you were a smart boy," she smiled and rubbed my thigh.

I gasped and nearly moaned feeling her hand that close to my private parts.

"Okay, baby boy, let's begin," she smiled. I noticed her full lips, so luscious and plump.

Again, she gave me butterflies.

The first 2 pictures were a cat and a dog. The cat on the A side was an ordinary house cat. Gray with black and white in its stripes. The dog on the B side was a cute little Shih Tzu. "What a cute puppy I gushed. I pick B."

Dr. Martin made a note of my selection and told me to continue.

The next 2 pictures weren't as easy for me. A was a Weeping Willow tree. B was a red rose. I couldn't decide. Both were pretty.

"My colleague said that this might stump you, baby. Take your time," she urged again rubbing my thigh.

Her hand so near was not really uncomfortable as was my arousal to her touching me. "The rose," I blurted. "I mean B."

Dr. Marin chuckled and squeezed my thigh. Okay, baby boy. Please continue."

The next 2 pictures were of two identical chairs. One was a brown leather over-stuffed chair. The other was a wing-backed chair. White with a floral pattern. I quickly chose the wing backed.

I turned the page quickly so as to try to ignore her hand rubbing me. The next photos were of two males. One was a real man. So ruggedly handsome and seemingly well built. The other was kind of like me. Short, thin, feminine when compared to the real man.

I pointed to the handsome man. "A," I said with a bit of enthusiasm.

"I thought you might," Dr. Martin said squeezing my thigh. "Almost done, baby boy."

The next 2 pictures were shocking. A was the same handsome man in boxer short. B was the little guy in what looked to be briefs. You could tell his penis was as small as mine because there was no bulge. While the little guy wore a look of uncertainty, the handsome man looked confident. After looking from one to the other, I finally chose the A.

"Okay, baby. We're making progress," Dr. Martin smiled. "Just a couple more sets for you to select. Don't be alarmed. I know that the next ones may be difficult for you to tell me but, johnnie, I need you to be honest with me."

Her hand on my thigh, her breath warm on my ear. I squirmed and wanted so very badly to adjust my boner.

The A photo was the back from the waist to the back of the knees of a man wearing baggy wrinkled boxer shorts. B was the same except the man was wearing boy-cut panties. The bottom half of his bottom showed. They looked so sexy I took a deep breath and quickly pointed to that one. "B."

I heard Dr. Martin take a quick breath hearing my selection. "I was hoping you'd choose that one, baby."

"Why, doctor?" I asked with a raging boner in my pants.

"Be patient, baby. Let's make our last choice."

I blushed as I gasped when I turned to the last two photos. "Oh my," I gushed. The A side was a big beautiful erection with a nice set of big balls under them. Side B was a little dick, much like my own. I stared at side A for the longest time as Dr. Martin rubbed my thigh.

The room was very quiet. "It's alright, baby boy," Dr. Martin whispered as she unzipped my pants. "Shh now. Relax," she blew in my ear as she pulled my throbbing erection out and stroked it a couple times. "I know which one you want to pick. It's that big hard cock, isn't it?

I nodded. My mouth was dry as Dr. Martin continues to touch my erection.

When I was moaning, Dr. Martin stood up. Raising her skirt slowly. I saw she wore hose held up with garters. Coming to stand between my feet, she looked at me and smiled. I want you to do what you feel you must, johnnie."

My eyes opened wide when I saw that Dr. Martin had a cock. It was thick and long. I looked up at her smiling face. "Come on now, baby. You know what you want to do."

Her hand touched my shoulder. That was all the sign I needed. "Ooooh, God," I groaned as I left the couch to kneel at her feet. I took her clean-shaven cock in my hand and rubbed it all over my face before holding her big balls and planting my face on them.

Her hands cradled my head. "Yes, my sweet sissy. You were made to service cocks my sweet cock sucker. Show me what you do to your wife's lover. Suck my cock like you suck Tom's."

I felt her moving about and had to move as her skirt slid down her legs. Walking backwards. I followed her on my knees to the chair where she sat.

I took her growing cock between my lips and used my tongue to taste her. I savored the taste of new cock and pre-cum feeling her grow hard. I lapped from her balls to the magnificent head pausing to look up at Dr. Martin.

She'd taken off her blouse and sat like a queen in her garter belt and hose as I became her cock sucker.

I sat back on my heels. Dr. Martin," I asked as I stroked her wonderful cock. "How did you know?"

"Oh baby, you radiate cock sucker. I knew it the instant I saw you. That's what you are. My diagnosis is that you, johnnie are a sissy. Unable to please women, you give yourself to a real man like Tom. You'll go through life servicing real men and women like me with cocks. Look at your little boner barely sticking out the front of your pants."

I looked down at my sorry excuse for a dick. "I see it every day, doctor. I know it's small."

"Small isn't the word for it, baby boy. Now if you don't mind, I'd like you to get back to work on my cock."

I reached for my dick and Dr. Martin immediately chastised me. "Don't you dare play with yourself while you are performing your nasty habit. Concentrate on making my cock happy; not your pathetic plaything."

I went back to sucking her cock as she explained herself to me. "Much like you, others saw me more suited dressing as a woman. I tried it and I liked it. I'm bi-sexual, johnnie, like you. But unlike you, I can satisfy my women. As you and I get better acquainted, I'll put you in touch with your inner sissy."

I licked her balls and mouthed her scrotum like Tom taught me. Then, using both hands, I quickly but gently stroked her cock while trying my best to deep throat her.

My knees hurt and my jaw was tired by the time that Dr. Martin announced her pending orgasm. "Alright johnnie, let's see if Tom taught you how to swallow a load."

Her cock expanded, pulsed and filled my mouth with a large first jet of sperm. Like Tom, Dr. Martin fed me pulse after pulse forcing me to swallow quickly so as not to lose one precious drop.

"Very good, johnnie. Like i mentioned earlier, Tom has trained you to be a top-notch cock sucker. Now, if you must beat off now, take a tissue and be damned sure not to get any of your sissy juice on my carpet. In fact, stand over the trash can and do it."

Dr. Martin knew instinctively how the humiliation would turn me on. I took a tissue and stood over the trash can as she busied herself putting her blouse and skirt back on.

She heard me groan as my climax came quickly. "Good boy. See you next week, same time. Now please go."

I hardly had time to put my dick away before she was hurrying me on my way. I had instant regrets as I made my way home. "Maybe I shouldn't have done that," I thought.

But I did it and I knew that my next appointment I would more than likely be required to do it again.

Tom was there when I arrived home. "Hey, johnnie. How was your day?"

"Um, it was fine, sir."

"Good. I'm glad to hear that. I don't want anything to interfere with the blow job I want."

"Uh, where's my wife?" I asked hoping I wouldn't have to suck his cock.

"Yeah, Cindy. She's out. Working late. She told me to tell you to cover for her. Get naked for me, cock sucker."

"May I shower first, please?"

"Make it quick. Will ya. This hard on ain't gonna suck itself."

I hurried before Tom changed his mind. Feeling the warm water washing over me gave me comfort. Thinking about what I was about to do, gave me an unexpected and rare second erection.

Tom was standing fucking my face when my wife walked in. "Thank God, Tom. I'm glad you used johnnie. I had a day from hell."

"Your boy gets the easy nut. I plan on wearing out that pussy of yours later."

"Uh huh. Promises, promises," my wife laughed and went to change.

Tom insisted I stay naked throughout the evening which was fine with me. As usual, I tended to the couple, pouring drinks, fluffing Tom, cleaning my wife's well fucked pussy after Tom was through with her. It wasn't that I resented their treatment of me that night. I was used to being bottom rung. While my mind was on the events at Dr. Martin's, my mouth was on sex organs.

Tom left and Cindy crashed. I lay beside her, still thinking about the casual way Dr. Martin seduced me. Showing me her beautiful cock was one thing. That she had a cock at all was more than surprising. "Here's a male for all intent and purposes who dresses like a woman and is not afraid to let others know. Not exactly a secret."

One thought led to another. I couldn't deny that I liked the look of that guy's bottom in those boy-cut panties. My dick jumped a little thinking about that photo. But two boners in one day wore my dick out. I rolled over and went to sleep.

As the week went by, I thought about my next appointment. I wondered if I was making a mistake. Dr. Martin had used me for her sexual gratification and discarded me as easily I discarded the tissue I used to catch my sperm. Even though it was humiliating to be brushed aside after sucking her cock, it turned me on. I planned to ask her about that. Was it normal or am I too fucking weird for this world?

"johnnie! Welcome. Come in, baby boy."

The way Dr. Martin welcomed me made me feel good, appreciated even. I smiled back. "How are you doctor?"

"I'm fine, sweet boy. But we're not here to talk about me, are we?"

"No ma'am," I agreed.

She sat across from me. Crossing her leg, I could briefly see the stocking top. "Now before I delve into your inner sissy, baby, do you have anything on your mind you'd like to ask me?"

"Yes, ma'am, I do. First, why was I so attracted to that photo of the guy in those pretty boy-cut panties?"

Dr. Martin smiled. Her full lips, painted a deep red, were so inviting. "I knew you'd be wondering why you got so excited by that picture, johnnie. It's pretty easy to understand, actually. A boy such as you subconsciously knows he's unfit to mate with women. He's desperate to attract real men. In that effort, a good sissy will do her level best to appear more feminine. Lingerie is a natural first step."

That surprised me and Dr. Martin could tell. "Let me ask you this, baby boy. Did you merely liked the way that male looked in panties or, and I want you to be honest with me and more importantly, yourself, would you like to have been that male?"

"I don't know. I mean me wearing panties, doctor. I admit that photo aroused me. I'm not sure why."

"Well, johnnie. There is one way we can solve your dilemma."

"How is that?"

Dr. Martin rose from her chair and went to her desk. I watched as she pulled a pretty pink bag from her Coach Purse. Smiling at me as she returned, Dr. Martin handed me the bag. "You can put these on, baby boy. Your reaction will tell us both if my theory is correct."

I knew what was in the bag I held. My hands trembled as I pulled out a delicate panty which was identical to the one in that sexy photo. "Dr. Martin," I begged. "Please don't make me put these on."

She smiled an understanding smile. "I know this is a big first step, johnnie. The first step is the hardest. But the first step is also important in you getting in touch with your true self."

"My inner sissy," I said weakly.

"Exactly that, baby."

The room was silent as I pondered what my doctor had said. "Well, someone wants to be in pretty panties," she said with authority. "Your little dick is hard."

I hadn't noticed but she was right. My dick was tenting my capri pants. I blushed a hot crimson.

"Nothing to be ashamed of baby. Just strip down and put them on. If you'd like some privacy, you can use the restroom."

I took a deep breath before deciding. "I'll use the restroom, ma'am."

My whole body was shaking as I removed my pants and briefs. I cannot explain it. To this day it remains a mystery to me. When I pulled those panties up and over my big bottom, it felt like I had removed some invisible weighty thing that had been holding me down. Dr. Martin would explain later that it was me blossoming into what I was born to be.

But at that moment, I felt freer than ever before. Free to be me. I looked into the mirror and decided that my shirt should be off. Removing that garment, I opened the door and introduced a new panty wearing sissy to my doctor.

"Heeeres johnnie," she smiled and clapped. No, she didn't sound like Ed McMann nor Jack Nicholson. But she sounded happy. And she was. Dr. Martin said we had a break-through.

"Let me look at you, my sweet sissy."

She came to me, first hugging me then having me turn and bend, modeling my new panties for her appreciation.

"Hold that pose, baby," she told me when I was bent at the waist. She came up behind me and I felt her cock rubbing my bottom between the cheeks. While she was humping my butt, Dr. Martin reached under me and stroked my dick through my panty. It all felt so wonderful and more. It all felt so natural, so right.

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