Sometimes a Cigar…

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My name is Bradley Steele, and I’m a psychologist. A therapist. A pretty good one, I think, but I’ve developed a … well, let’s just call it a “quirk” that would probably make me suspect in the eyes of my colleagues.

I’ve been in practice a couple of years now, and done pretty well. Every now and then I get a client who wants to be counselled about gender identity issues – always cross-dressing men, and they always want me to somehow cure them of their femininity. I’m not comfortable with that: these aren’t men who just enjoy occasionally wearing women’s lingerie, or they wouldn’t be coming to see me. They seriously believe they are women in men’s bodies, and I can’t help them to be something they’re not. So, I refer them to doctors who specialize in the field and, as far as I know, they’ve all eventually made the decision to transition and live full time as women – whether or not they’ve actually undergone hormonal or surgical therapy.

My practice consists of a waiting area, overlooked by a receptionist’s office, and my own inner office with its own exit, so that my patients don’t ever run into each other. One evening, I’d seen my last client, sent my receptionist home and finished some paperwork, and was just about to head home. Ellen, the receptionist, always locked the front office door as she left, and I was leaving through the back door.

As I turned to make sure the door was locked, a woman’s voice behind me said “Hello, Doctor Steele.”

“Oh. Hello – do I know you?” I faced a rather plain brunette whose distinguishing features seemed to be enormous breasts, barely contained by a too-tight blouse above a too-short skirt – that, and the fact that, even though I’m over six feet tall myself, in her high-heeled boots she was noticeably taller than me.

“Indeed, you do. But you won’t remember.

“I used to be called Carl, but now I go by Karen. I wanted to thank you for everything you’ve done for me.”

“Carl?” I remembered. Carl had been the first transvestite who’d wanted me to make him a happy man, and now here he – no, she! – was. Apparently, content in her new life.

“Sure, I remember you, Car … er, Karen.” I had a sudden feeling that it might not be in my best professional interest to be seen standing in the hallway talking to this strange woman. I didn’t know what she really wanted, but decided it would be better if I found out in the privacy of my office.

“Why don’t we go into my office and chat?” I asked her and, unlocking the door, I hustled her inside.

As she walked over to my couch, I quickly activated the keyboard sequence on my computer that turned on the hidden video camera. I always tape my client sessions, to ensure that nobody could come back later and accuse me of anything improper, but in this case I was more worried that perhaps Karen actually felt I’d ruined her life and wanted revenge – and I felt I needed an objective record of events.

I’d been too involved in my own actions, though, to see what Karen was doing. As she reached the couch, she turned around. Her blouse was wide open, and she was already shrugging it off her shoulders, as she pinched open the front clasp of her gigantic bra.

“Do you like them?” she said, as she let the bra and blouse fall to the floor. “38DD.” She cupped them in her big hands and pointed them at me.

I tried to answer, but my mouth had gone dry, and I couldn’t say a word.

“Oh, I see you do!” She stared down at my rapidly expanding crotch, then dropped to her knees in front of me and began to stroke it through the fabric of my pants.

“Ooh – is it as big as it seems?”, she asked.

“St…” I tried to tell her to stop, but I still couldn’t get a word out.

Before I knew it, Karen had my pants down around my ankles, and was lovingly licking my full nine inches.

“It’s beautiful, Doc. And so much bigger than my boyfriend’s. I bet you have to beat off the women with a stick.”

Before I could even try to answer, she had engulfed my cock; her hot velvety mouth sucking me in deeply before almost spitting me out, and then repeating the process.

“Oh, my God!” I finally found my voice. “That feels incredible!” Somehow, even though I’d had dozens, maybe hundreds, of blow-jobs, this one from a transsexual woman was turning me on more than I’d ever been before.

I looked down to see her staring back up at me, as my shaft pistoned smoothly into the back of her throat. Karen had managed to unzip her skirt as she worked, and it was now puddled around her knees; her right hand diving into scarlet lace panties to stroke her own rigid tool.

The sight was too much for me, and I came explosively in her mouth.

“Ah!! Oh, God! Ahhhhh!” The first wrenching burst of come filled her mouth to overflowing, and she opened her mouth to take the second ejection full in her face, as she tried to swallow the first load. Then she took me back in her mouth for one last spurt, which she allowed to dribble down onto her massive tits. She looked Ümraniye Grup Escort up at me with a grin as she cleaned my softening member with her tongue, alternately scraping my come off her cheeks and licking her fingers.

Karen stood and, putting her arms around my neck, kissed me deeply. She’d swallowed everything, but I could still taste myself on her tongue, and was surprised to find that even that excited me.

“You got some on my tits,” she said, breaking the kiss. She pulled my head down slightly and I let her guide me to those amazing globes. My lips touched the first glob of semen and I knew what she wanted from me. I let my lips open, and tentatively swirled my tongue over the sticky mess.

“Yessss!” she hissed. I cleaned both orbs thoroughly, taking extra care to tease and stretch her swollen nipples. Karen gave me approving murmurs as my tongue and lips did their job, guiding my head to new locations as necessary, but always letting me come back to play with her stiff nubs. When she’d had enough, I felt a gentle but insistent pressure on my shoulders, and let her push me to my knees.

At eye level, I could now see her cock poking out of the top of her panties. Hooking my thumbs in either side of the waistband, I peeled them down, freeing a sizable appendage. It was smaller than mine, but probably larger than average. It looked like heaven. I leaned forward to kiss the head, but Karen was through being patient. I felt her large hand wrap itself in my hair, and twist. As I gasped, I heard her say “Suck it, bitch”, and she thrust her whole length inside me.

I had no control of the situation, and Karen wasn’t asking for a blow-job. She was face-fucking me, hard. With each thrust, I felt her huge knob tear into my throat. I gagged and choked, and she’d hold me there, with her pubes tickling my nose, until the tears streamed down my face. Then she’d pull out and let me gasp one small breath before slamming back into me. I should have felt abused and demeaned. I should have felt violated. I should have felt pain. Instead, all I felt was excitement. My cock was already hard again, and I was jerking it for all I was worth.

From a distance, I could hear Karen encouraging me. “Yes, that’s it faggot… Suck it, suck it deep… Oh, yes, Yes! YES!!”

She pulled out, and holding my head at arm’s length, sprayed my face and shirt with her seed. Simultaneously, I came all over my hand and the lower half of my shirt. She pushed her cock back in my face, and made me clean it off as she had done for me. Then, when she released her grip in my hair, I collapsed, exhausted. I slowly dragged myself over, and on, to the couch, then turned back to look at Karen.

“Thanks, lover,” she said. “I needed that.”

She’d zipped up her skirt, and was refastening her bra. Now, reaching for her blouse, she grinned at me and said “We’ve both been very, very, bad. I’m going home to my boyfriend to confess. He’ll spank me, and fuck my ass so hard, I won’t be able to sit down for a week. Have you got anybody to spank you?”

Again, I couldn’t talk, but now there was a reason. My throat was raw and starting to throb. I just shook my head.

“Oh, well, I’m sure you’ll find someone, now that you’re the Bitch Doctor. Thanks, again.”

With that, she turned and walked out the door. I never saw Karen again, but she’d changed my life.

I slumped, exhausted, on the couch for at least a half-hour. Finally, I realized I needed to clean up. It wouldn’t do for Ellen to come in and find any evidence of what had just happened. First, I made sure that both doors to the office were securely locked, then stopped the video recording. I had to erase the recording, but first… I decided to watch it. I watched it three times, getting more and more excited each time, before finally coming again. As I watched, I was greedily cleaning the come off my face and fingers, swallowing every drop, then sucking every drop off my shirt, trying to tell the difference in taste between mine and Karen’s, and deciding which I preferred (hers). I couldn’t decide which was the best part of the video – seeing her stroke her own cock as she swallowed mine, or watching myself gag on that first thrust as she raped my face. Both were pretty exciting, and the third time Karen climaxed on-screen, I let myself come with her, spurting into my hand and then cleaning myself with my tongue once again.

Quickly, I edited out the dead space from the end of the video, and put the resulting file on a memory stick, before removing any evidence of it from my computer. Then I set about cleaning up the office. The first thing I discovered was the lacy red panties – in the middle of the office floor. I hoped that was the only souvenir she’d left. I’d be in trouble if a client found something like that tucked in the couch!

I only found a few spots of semen on the floor, which I hastily cleaned up with a tissue – I’d get the office cleaners to do a more thorough job in a few days. Ümraniye Manken Escort No doubt the office smelled of sex, but I knew Ellen kept a bottle of Febreze in the office, and hoped that would take care of any scent. I sprayed the carpet, couch, and my desk chair.

At last I was ready to clean myself up. I must have looked a mess – there were surely cum-spots I’d missed, particularly in my hair, but I had no mirror available. I grabbed my sports bag from under the desk, and started to change into tee-shirt and shorts. My eye was caught by Karen’s panties, and on the spur of the moment, I put them on beneath the shorts. I put on my trainers, and stuffed my work clothes and shoes into the bag. I dragged a comb through my hair and left my office. The men’s washroom was just twenty feet down the corridor, and at this time of evening I wasn’t likely to meet anyone. I was able to get cleaned up – indeed, there was still a huge gob of come in my hair, just above my right temple, which of course I wiped off and swallowed gratefully. I washed my face, cleaning up the evidence of tears and semen, but there was nothing much I could do about the bruising around my lips – and headed home to my penthouse apartment.

* * *

Normally, I pride myself on my culinary abilities, but I couldn’t even think of making supper. I poured myself a glass of wine, but the alcohol made my throat burn and I switched to ice water. I sat down at my computer and started looking for information about cross-dressers and transsexuals. I thought about what had happened, and how much I enjoyed it. Was I gay? (Karen had called me a faggot – did she know me better than I knew myself?) Was I transsexual?

The more I “researched”, the more I found myself merely watching videos of women like Karen. I realized that though I was attracted to their penises, I was not attracted to men who looked like men. I was attracted to women with dicks. I also realized that being face-fucked once was enough – in future, I wanted to be the one in control. I started to imagine my ideal woman: height – approximately 4-6 inches shorter than me, so that we’d be close when she wore heels; slender but with a shapely butt; blonde (well, anyone can be blonde!); breasts – preferably B’s, definitely no larger than C – I subscribe to George Carlin’s theory that anything more than two handfuls, a mouthful, and a little left over is wasted.

I ended up spending the whole night online, and in the morning I was in no shape to work. It turned out not to matter, as I realized my throat was so sore that I couldn’t talk. I sent Ellen an email telling her I had laryngitis, and asking her to reschedule all my appointments for the next two days, and also to call the guys I had booked squash games with for the rest of the week. Then I phoned her cell and croaked to her to check her email, so that she’d understand just why I couldn’t work…

For the next two months, I spent all my spare time online, jerking off to videos and stories of transsexual women, always wearing Karen’s panties. I wore those panties out, but it really didn’t matter: I didn’t want to wear lingerie myself, I wanted to find a guy who looked good in lingerie. I tried to come up with ways to find that perfect woman, but in the end it was pure serendipity.

I play squash, at a racquet club next door to my apartment building, three to five times a week, and one day a regular partner introduced me to a guy named Stu.

“You two should arrange a game – Stu’s sure to give you a better game than I manage. He may be small, but he’s fast, and I’ve never managed to beat him.”

“Sure – what do you play, Stu? Hardball or softball.”

“Either’s fine with me.”

“I’m strictly softball – some say it’s a harder game, but as far as I’m concerned, that hardball just moves too damn fast for me!”

So, we set up a game for the next morning before work. I commented that he looked vaguely familiar, and asked if he lived in the neighborhood, and it turned out he lived in my building. I just assumed that that’s why I recognized him, that that was all there was. But one day, as I entered the club, I saw Stu behind a couple of women. All I could see was his head and shoulders, behind these two fashionably dressed women, and I was initially thinking I was looking at three women. Suddenly it hit me. I didn’t remember Stu – I remembered a young lady I occasionally met in the elevator. She was much the same size as Stu, but a little taller – but she was always in heels when I saw her. And now that I looked closer, she looked just like a blonde version of Stu in drag.

I’d have felt pretty stupid hitting on Stu, only to find he was straight and the woman just happened to look like him, but I had a simple plan. Our building was pretty upscale, and we had a security guard in the lobby 24/7. I’d always been friendly with the staff, and gave them all Christmas tips, so I waited till my favorite guard was on duty … and bribed her. I knew what floor Ümraniye Masöz Escort the girl got off on, and asked for Stu’s apartment number. Match. Then I asked who was on his access list (people the guards will let in and send up at any time). His mother, and his cleaning lady (I knew that’s what she was, because she was my cleaning lady), but there was no second tenant. After that, it was a simple matter to be home when my cleaner arrived at my apartment one day and get her chatting. I mentioned that I’d discovered that she also worked for my friend Stu and asked if she’d ever met his sister. She told me that although the sister apparently lived there – because the second bedroom was full of women’s clothes – she’d never met her, there were no pictures of her anywhere, and she didn’t seem to spend much time there as the room was never disturbed: it just needed dusting regularly.

“He tells me she’s beautiful,” I said. “I’m going to have to meet her one of these days.”

In the end, it was almost anti-climactic. Stu and I started playing squash a couple of times a week. Squash is played on a small court, and players are always going to get in each others way. I made sure that every time I could make contact, I did – not hard, just touching him. I awarded myself bonus points if I could “accidentally” put a hand on his butt (and double bonus points for his crotch).

One morning, we were playing early before we both left for work, and I was getting more contact than ever. I could see he was getting aroused, but pretended not to notice until finally as he tried for a shot, I turned directly into him. He ran right into my arms, and I could feel his erection pressing into my left thigh. With my hands on his hips, I leaned forward and kissed him on the lips. Stu blushed and stiffened, but I just turned around and picked up the ball.

“Your point, I think.” I tossed him the ball.

He served sloppily, and I proceeded to take seven straight points to win the match. I picked up my towel and leaned back against the court door, blocking the little window that was the only way to see into the court. I laughed as I wiped my face. Stu looked at me in a daze.

“What was that?”


“You… you kissed me!”

“Come on, don’t tell me you didn’t want me to.” I reached for his hand, and pulled him towards me. He didn’t resist.

“You did, didn’t you?” I pulled him closer, and kissed him again. This time I pushed with my tongue, and his lips parted. He began to respond, and as our tongues wrestled I stroked his cock through his shorts. It wasn’t long before I felt his cock jerk under my hand, and he came in his shorts. I put both hands on his shoulders, and still kissing him, started to push downwards. He resisted at first, but I’m much bigger and stronger than he is, and he accepted the inevitable and sank to his knees.

“Take it out” I commanded, as he stared at the bulge in my shorts.

“What if somebody tries to get on the court?” he asked.

“Nobody is coming through that door until you finish what you started.”

He was obviously not thinking straight, or he might have mentioned that it was me who started it, but instead he very tentatively reached forward and touched my cock through the shorts.

“That’s it,” I told him, as he started to feel it’s shape. “Go on.”

He hooked his thumbs in the waistband and started to pull my shorts down. They hooked briefly on my shaft, and he slid both hands forward to pull it clear, then back again to my hips, continuing to slide the shorts down my thighs as my prick sprang forward in all it’s glory. The head struck his cheek, and he brought his left hand up to hold it still as he guided it to his waiting mouth.

Stu obviously hadn’t done this often, if at all, before, but what he lacked in technique, he made up for in energy. He bobbed his head rapidly on my cock, sucking and slurping but never quite managing to get any more than half of my nine inches inside him.

“That’s it baby, suck my cock…

“That’s the way, you little cocksucker…

“Oh, that’s so good, baby…”

I kept encouraging him. It wasn’t really that good, and every time my cock came close to the back of his throat he gagged and backed off, but I was willing to take my time with him. I wasn’t going to force him the way Karen had forced me – and in any case, I wasn’t that attracted to Stu, I wanted his “sister”. Still, I’m a man, and like any man it’s hard to resist the lure of a warm hole to shoot my load in. Pretty soon I could feel my balls tightening.

“Oh, yeah! I’m going to come, baby. I’m going to shoot in your throat…Swallow for me baby! I’m cuuummming! Oh…

“That was great,” I told him as I helped him stand. “Let’s get outta here.

“You’re going to need your towel,” I said – pointing to the dark wet patch on the front of his shorts. He tried to hold the towel nonchalantly in front of his crotch as we walked back to the change room, where we both quickly changed into street clothes, opting to skip the showers this morning.

We walked back across the park to our building side by side, but not touching or speaking, until we got into the elevator in our building. As soon as the door of the elevator closed, I pushed Stu against the wall and kissed him again.

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