Carl, meet Joan

"No, no, tomorrow is fine. But, I will not tell you where - I will pick you up here, and the rest will be a surprise."

"You can't do that! How will I know what to wear?"

"Wear something elegant - that's as much as you need to know."

"You - you - can't do that!"

"Yes, I can," I said, with a smug smile, "something elegant - I'll wear a suit!"

She gave me a look, and I think she was going to argue, but then she conceded.

"OK, then what time?"

"That I will tell you tomorrow, once I have made a reservation!"

"OK then. Now - out and let me fantasize and anticipate a date. For what are now obvious reasons, I have not dated much, and I am going to try to keep my worries down and focus on the anticipation part."

I kissed her again - with passion.

"No worries!" I said. "Thank you for the wine, for trusting me, for agreeing to the date!"

"I don't know if I can believe that this is real, but right now I am walking on air!"

I left her apartment and headed out the door.

"Good night, Frank!" I said to the doorman.

"Oh! Good night Carl!"

As I drove home, I wondered what the hell I was getting myself into. Was I seriously dating this woman/man? "She has a dick!" I told myself. But still I was infatuated with her, and I kept telling myself that nothing would happen until after her bottom surgery.

I slept fitfully that night. I actually had a dream about sleeping with her and her dick. What did it look like? How big was it? What if it was bigger than mine? Does this make me gay? Bisexual?

I made a reservation at a fairly swanky place for 7:00, and I called Joan.

"You called!" she exclaimed as she answered.

"Of course, I said I would!"

"I - well, I let my worries creep in."

"No creepy worries!" I said to her. "I will pick you up at 6:30 - we have reservations at 7:00"

"Really, where?" she asked.

"Uh-uh! I told you it's a surprise!"

"Darn it! I was hoping to trick you!"

"I'll see you at 6:30" I said to her.

"OK - I have to go shopping!" she said.

"For what?" I asked.

"An elegant dress - and a matching tie! So - a white shirt so I can fix you up with a tie that works with my dress, so everyone will know that we are together!"

With that she hung up.

I had nervous energy, so I went for a run. I got home and showered and shaved and got dressed in a suit. I skipped the tie.

I stopped at a florist shop and bought her flowers, and then headed to her place. I pulled up at 6:25 and got lucky with a parking place right out front. As I was getting out, she came strolling out of her apartment building wearing a dark blue dress with a slit in the skirt that went about half way up her thigh. The bodice was a halter-type with the back that was cut low, showing off her shoulders and back. Her strawberry blonde hair framed her face just so, and I felt an immediate stir in my groin.

I walked to her, and extended my hand, which she took. I held her hand high up and she gave me a twirl.

"Oh. My. God!" I said, "you look SO SEXY in that dress!"

I did not think that the smile on her face could have gotten any bigger until I presented her with the flowers.

"They're beautiful!" she said.

"No, they pale in comparison to you!" I replied.

"You're a bullshitter! For you, my prince charming!" she said, handing me a tie that matched her dress color perfectly.

"How did you find a tie that matches perfectly?" I asked.

"At the right boutique, they actually have ties made to match the dress."

"I never knew that," I replied.

"I didn't either, but luckily my friend Sarah knew."

"Sarah?" I asked.

"Yes, she's been my confidant since middle school. The only one who 'got' me when I decided to move forward with the transition. Actually, she's the one who suggested that I not just ignore your first advance - she's why I approached you at that second meeting."

"I will have to buy her flowers, too, then!" I said.

"Hmm, OK, but a smaller bouquet than mine!" she replied with a smile on her face.

"Deal."

I opened the car door for her and she slid into the seat. I sat in the driver's seat and started to put on the tie, but she took it from me.

"Look at me!" she said as she neatly tied it for me.

The restaurant was as chic as it was built up to be.

"The prices here are outrageous!" she whispered to me.

"Totally worth it for you, my dear!" I replied.

We had a wonderful dinner and wine and I paid for the meal and as we walked back to the car I put my arm around her. I drove her home, and kissed her in the car.

"Please come up for a night cap," she said.

I eagerly accepted.

"You can park in the garage. There are a couple of guest spots, hopefully one is open."

I used her garage pass to get in, and sure enough, one of the guest spots was free.

We took the elevator up to her apartment and as she closed the door she kissed me.

"Please take off the jacket and tie - to again use a cliche, I will put on something more comfortable.

I hung the suit jacket and tie on the coat rack by the door. I put on some music on her stereo and sat down. She appeared from her bedroom wearing some loose fitting pants and a blouse, and, it appeared, no bra, as I could see her breasts swaying and her nipples were rather pronounced.

"Sorry to look so slovenly compared to you!" she said. "Carl, I can't thank you enough for the date - I truly have not been on very many, and you made it so special for me!"

She sat next to me and kissed me again. Our kisses grew very hot, very fast, and in spite of the inner war going on in my head, my cock quickly got quite hard. My hands roamed to her breasts and she moaned as they did. Her nipples were quite sensitive and stood out prominently as I caressed them through her blouse. She unbuttoned my shirt and pulled it off, and I started to unbutton her blouse.

"Carl?" she asked, "are you sure?"

"My infatuation with you has only grown - you looked so sexy in that dress, and you look so sexy in your 'slovenly' attire now. I don't care any more what it all means, I just want to be with you!"

She sat back and finished unbuttoning her blouse and slowly pulled it back and over her shoulders, showing me her breasts and her belly. She had freckles that spilled from her face, down her neck, but they grew sparse and then disappeared from her soft breasts.

"Do you like what you see so far?" she asked.

I answered with a kiss to her lips, and a hand running over her chest. My kisses trailed down her neck, under her ear, on her ear lobe, down over her collar bone, and then down - down to her right breast and all around, and finally to her prominent nipple. My tongue flicked out over it and she gasped at the attention, her hips wiggling as she did.

I moved to her left breast and followed the opposite trail back up to her shoulder, her neck, her ears, and finally a kiss that I hoped was full of passion on her lips.

She looked at me with a look of satisfaction, lust, and a little bit of fear. As I looked quizzically back at her, she again pushed me back against the arm of the couch and put herself on top of me. Without a word she began kissing her way down - down to my chest and across my abs. As her kisses went further south, her hands unbuckled my belt and unfastened my pants, easing the zipper down. The suit pants opened and with only a slight push up of my hips, she had them on the floor. I kicked off my shoes and she pulled off the socks, leaving me in a very tented pair of boxers.

I don't really know how I compare to other guys - I was never into those kinds of locker room contests, but maybe I'm above average. She carefully took the waistband up and over the protruding head and slipped them off, too. She gave a little squeal at the sight and began to kiss and stroke me. She ran her tongue from the base up to the head, and ran it around the crown, and then opened her mouth and took me inside, her tongue continuing to swirl around me.

I thought that this must be heaven. I let her continue for a while, but was afraid that I was going to blow my load too quickly, and I pulled on her shoulders to get her to move back up. I kissed her fully, her tongue fencing with mine and I tasted a new and different taste.

"You don't want me to finish?" she asked.

"Not just yet," I replied. "There is an unevenness that needs to be taken care of!"

The look on her face went to one of fear.

"I - I don't know if I'm ready for that!" she said.

"Oh - OK, I don't want to force anything. You're ready to give me head and make me cum, but not this?"

"I'm s-still afraid."

"Afraid of what?"

"That you'll reject me. I have boobs and you seem to like them, and..."

"I do! I like them very much!"

"Yeah, but what's down there is not what you're expecting - it's not what you want," she said, and again, I could see tears welling up.

"Joan, you need to catch on!" I replied, kissing her, "It's YOU that I want! You, in whatever form you are in!"

"You're just saying that!"

"If I was just a horny guy - and right now you have me as a horny guy! If I was just a horny guy looking to get his rocks off, why would I have stopped you? From the moment I said that I wanted to date you, and even after you telling me more about you, I still wanted a date. I knew where it might lead, and now that we are here, I want YOU. To misquote a TV show, I want you, naked and unafraid! I'm quite smitten with you and I want us to take that wherever it leads!"

She kissed me again with passion. The kiss went on for a long time. When she stopped, she stood up, and loosened the pants she was wearing. I stepped up from the couch, and dropped to my knees in front of her.

"Let me?" I somehow stated and asked at the same time.

"O - OK - I think?" she replied.

I took the waistband from her, and I looked up at her. She was looking down at me with a look of combined fear and lust. I tried to be as kind and caring as I could.

"Trust me? I will admit to being a bit afraid, myself, but as I said, I really want to be with you - in whatever form!"

She nodded at me, and I gently slid the pants over her hips. She was wearing a thong style pair of panties and outlined underneath was a stiff penis. It spared my fragile male ego to see that I was quite a bit larger, but it was definitely there. I pushed the pants past her knees and they fell to the floor and she stepped out of them. I then reached for her panties, and I looked up at her as I did.

"It's OK, Joan, I want to see and know all of you!"

The smile on her face at that instant was worth gold to me.

I gently pulled her panties over the stiff cock, and over her hips. Her hips and ass were definitely feminine looking. Her cock was only about 4 inches, and her ball sack was small, too. Her pubes matched her hair - strawberry blonde, and were a sparse bush at the base of her cock. Surprising even myself, I leaned in and kissed her head. As I let the panties drop past her knees, I moved my hands up and grabbed her ass and pulled her toward me. My tongue snaked from my mouth and I licked her small dick.

"I'm really sensitive under," she said.

"Under?"

"Yeah, between the base and the balls."

I ran my finger down her and when I got just at the base I pushed a bit and she went weak in the knees.

"Oh, yeah, right there!"

I leaned down and I kissed the spot. I ran my tongue up her shaft and then back down and tried to apply extra pressure just there. I cupped her balls in my hand and then decided to go for it. I ran my tongue back up the shaft, and when I got to the top, I opened my mouth and took her inside me, trying to run my tongue over the head the way she'd done it for me.

"Oh my God! Carl! I can't believe you're doing that!"

I kept sucking on her. My hands was still massaging her balls, and running up and down her shaft. Feeling her knees weaken even more, I moved her back to the couch and she sat, opening her legs.

I looked up at her and I smiled.

"I want to make you cum, my dear!" I said, lowering my head over her again.

Her hips moved up and my mouth went down on her again. I could almost get all of her in my mouth. With her legs splayed out, I ran a finger over her perineum and teased her bum hole, but mostly I was concentrated on her dick. I kept sucking and licking and teasing until I felt her hips begin to thrust forward.

"Carl! I can't hold back anymore!"

Without a word, I kept bobbing my head on her.

"Carl! Carl! Carl! Cumming! Oh God! I'm gonna cum! Oh God!"

Suddenly her hips pushed forward again and I felt her warm cum flood my mouth. I quickly swallowed, but another spurt shot forth, and I opened my mouth and it spilled onto her balls, and onto my hand that was still playing with her back door. I swallowed more and as her orgasm crested and then settled, I ran my hand up her cock squeezing the globs of cum from her. I ran my tongue down her shaft and over her cum-soaked balls. I licked her cum from my hand, sucking my fingers noisily.

I looked at her and smiled. The look on her face told me everything. The fear was gone, and satisfaction and lust were all that remained. She pulled me up to her, and we kissed, her tongue pushing into my mouth, tasting her own cream.

"I can't believe that you stopped me, and then did that!" she said.

"Well, I must confess something."

"What's that?"

"I knew that I wanted to do that for you, but I was afraid that if I came first, then I'd lose it, so you had to be first."

"I see," she replied, "well, I came first, but I still want to do that to you, so get your ass up here, and we can switch places!"

Having not cum yet, I was more than willing to do so. She lowered her head onto me. I was only about half hard at this point, but in her warm mouth I quickly stiffened again. She ran her nails lightly over my balls and perineum and over my back door. I'd never thought about my butt hole as sexually sensitive before, but the sensation of her fingers at my rear entrance heightened the sensation of her tongue on my cock. It was not long with her sucking, licking, pumping on my cock and her fingertips playing with my balls and ass before I felt the urge to cum.

"Joanie, I'm gonna cum soon!" I said as a warning.

She pulled her head back and slid me from her mouth just long enough to say "Good!" and then again took me in. Rubbing her fingers strongly on the underside of my shaft at the taint area and sucking again on my head, my hips lifted up as I shot spurt after spurt into her mouth. Like me, she couldn't seem to hold it all, and some of it dripped from her lips onto my belly, but clearly she was swallowing what she could.

As my I came down from the orgasm, I laid my head down on the couch trying to get my breathing back to normal, and I felt her move up to me. Before I could think she was kissing me with a mouthful of my cum, just as I'd done to her. I was in my post-orgasmic "refractory" time, but I opened my mouth to her and tasted myself for the first time. My gut reaction was to reject, but my brain said that I needed to do it for Joan, so I accepted and returned her kiss. In a couple of seconds I had settled into the part where this is sexy - sloppy, but sexy.

She lay down on top of me. I could feel her prick between us, her breasts soft on my chest. I did not know where all of this was leading, but I also knew that this was a journey that I very much wanted to take with her.

"Will you stay?" she asked.

"I'm right here," I replied.

"No, I mean stay - sleep here, in my bed with me? I will make you breakfast tomorrow."

I kissed her again.

"I really like the sound of that - staying. Well, breakfast, too, but staying with you. I didn't bring any PJs though."

She looked at me, at us, lying naked on the couch.

"I don't think that's an issue! Come on, I need to go pee, and I bet you do too!"

She was not wrong about that.

We stood together and I watched her walk ahead of me. Everything about her was feminine - her walk, her round ass, her breasts, her face. Even the penis was kind of feminine. I was totally taken with her - enough so that I really didn't think about, or didn't care about the kind of sex we were having.

We each took our turn in the bathroom. I didn't have a toothbrush so I just used some toothpaste on my finger. When I walked back into the bedroom, Joan was lying in bed with the covers up.

"I was going to just lie her, but I got a little chilly. Come warm me up!"

I climbed into bed with her and she rolled so that we would spoon together. I wrapped my arm around her and snuggled in. The feel of her buns against me as my hand lazily caressed her breast started a rise in my cock.

"Sleep!" she said to me.

"Yeah, I know, I want that, too, but if you are going to lie here naked and rub that gorgeous ass against me, this is what you get. Take it as a compliment!"

"Compliment accepted! Good night, Prince Charming!"

"Good night, fair maiden!"