Best of Both Worlds

Author's Note: The following story contains scenes that are fairly taboo. All persons are over the age of 18.

****

My name is John Smith. I am an executive for a major retailer in Atlanta, Ga. I am 38 years old, single, stand 6'1" tall and weigh an even 190. I have dark brown hair and brown eyes and a fairly handsome face. My body is lean from running and I do that pretty much every day to stay in shape.

I often go down to the sales floor and walk around several times a day. I mainly want to see how the floor displays look, observe the clerks and other sales people and just get a general sense for my people's moods. Most everyone knows who I am and some will nod or wave while others will avoid my gaze entirely.

I was walking the floor one afternoon when I saw this striking woman checking me out. I noticed that she was one of the sales people by the color of her golf shirt. I made a mental note of her petite size and large chest and continued to make my rounds.

I remember looking up and seeing her peeking at me from behind a stack of clothes. I smiled at her and she smiled back. I then moved down the stairs and over to the outdoor section. I turned and there she was again. It was if we were playing this game of cat and mouse.

I began to fantasize about this mysterious woman. It had been some time since I last had sex and I was ready for a fling of some sort.

There she was again, peeking at me around another display.

I decided to take the direct approach and just ask her what she wanted, but when I turned around she was gone. Hmm, interesting.

A couple of days went by and I didn't see this woman anywhere. Maybe she was a temp hire. The company does that on occasion. People will show up one day and be gone the next.

I was looking at a display and walked over to get a better look when I almost collided with this woman.

"Oh, hey! Sorry about that." I said as I retracted my arms. (my hands were dangerously close to grabbing her breasts.)

"No, I'm sorry sir." She said and looked down.

"Samantha!" I said, looking at her name badge and saw her nipples protruding from her shirt.

"Yes sir. Hi." She said demurely and shook my hand. Her eyes looking down again.

"It's okay Samantha. My eyes are up here, by the way." I told her and chuckled.

"Sorry sir, I'm just really nervous talking with you." She said anxiously shifting from one foot to the next.

"Oh? Why's that?" I asked her.

"Well you're the big cheese around here sir and I am worried that I might say or do something that might upset you." She said honestly.

"No worries there Samantha. I'm just a man with a big throbbing title." I told her.

"Okay sir." She replied and giggled.

"Enough with the sir business. My name is John." I told her.

"Okay...John. Can I ask you something?" She inquired.

"Sure Samantha. Shoot." I told her.

"Is there a Mrs or a Miss in your life?" She sked.

"Well no, not at the moment. In fact there hasn't been one in my life for some time. I'm just so busy, there's not enough hours in a day for much of anything romantic. (I moved my hands to show my index finger going into the okay sign of my left hand.) It's just me and my hand. Sorry, now who is the one acting all nervous?" I laughed.

"It's okay. I wasn't trying to pry John. You are a handsome man and you probably have plenty of women who are much prettier than me vying for your attention. I just thought that I could give you a helping hand or you could give me one?" She said coyly.

"Uh yeah. Sure. Like you mean right now?" I asked her.

"Uh-huh. The dressing room is right over there. You can meet me in it in say 2 minutes?" She winked.

I looked at my watch and then around to see who was on the floor. "Okay. Got it!" I told her.

I watched as she sashayed away. I was walking on thin ice but I was horny too. And this gorgeous woman was coming on to me? Who knew?

I casually made my way over to the dressing room. I walked in and saw that she went into the furthest one in the back. I opened the door and then closed it and locked the lock.

"So how do we do this?" I whispered.

"You help me out and I help you out." She told me in her feminine voice.

"Okay, but I kind of need some incentive first so why don't you show me your breasts." I told her.

Samantha took off her shirt and she was wearing a black lace bra.

"Oh that's nice." I told her.

"You can touch my tits if you want to John." She told me.

She unzipped my pants and reached her hand in and pulled out my semi-hard dick. "Ooh it's big." She cooed.

(It's not that big. It's only eight inches long and when hard it curves up like a banana.)

I looked down and saw that my dick did look big in her palm and went half way up her forearm.

I placed my fingers inside the lacy sides of her bra and her skin felt smooth. I worked my fingers down into her cups to find her nipples, when she released the clasp in the back and her bra fell to the floor.

Her breasts were huge and had dark areolae and long thick nipples that resembled thimbles.

"Oh my. Your breasts are nice.!" I told her nervously.

"Go ahead and touch them silly." She told me as I just looked at her breasts with my mouth open.

She took my hands and placed them on her breasts. But when I didn't do anything she turned around and clutched my hands to her breasts.

"Go on and work my nipples John while I finger myself. That's it. Harder. Pinch them. Mmmm, yessssss. Harder baby, harder, HARDER!!!" She growled.

"I'm almost there John. Mmmmppphhh mmmpphh. Ohhhhh. I'm cummmiiinnnggg!!! (She squealed) That was nice. Now it's your turn sweetie." She said and got down on her knees in front of me.

Samantha took out my dick and stroked it up and down and then put the head in her mouth. She slurped my dick and stroked it and in only a few minutes I was having an orgasm. I didn't warn her though and my first blast went up her face and into her hair before she clamped her mouth over my head.

It had been awhile since I last got off and I shot a good bit of cum in her mouth. 7 massive blasts I shot including the globs that came out and went on her face and into her hair. Samantha swallowed everything and even sucked the remainder that was left in my shaft when my dick went limp.

She put my dick back in my pants and zipped me up and then turned and used her fingers and got the thick globs that hit her cheek and forehead and licked those from her fingers. She picked up her bra and put it on and turned and smiled at me.

"That was awesome! Same time next week?" She said smiling.

"Yup." I smiled and left the dressing room a new man with a new bounce to my step.

****

She was waiting for me in the dressing room only this time she was naked from the waist up.

I wasted no time and grabbed her tits and pinched and plucked her erect nipples for several minutes before she turned around and I really dug my fingers into her tit flesh.

Samantha cried out in orgasm and then she turned around and unzipped my fly and began to deep throat my dick until I blasted my cum down her throat.

We repeated this week after week and then I asked her out.

****

Samantha met me for dinner at a nice Italian place on Peachtree street. She showed up in a sleek black dress that really accentuated her breasts. She looked stunning and I had trouble concentrating on eating I was so mesmerized by her beauty.

We talked about our families, our life before this company. I asked her about her past loves and she asked about mine.

I found it interesting that we were the same age, grew up in the same area and went to the same high school and yet I never knew she existed. Funny how that is sometimes.

We finished dinner and she followed me back to my house in Marietta. We walked in the door and she was all over me. Off came my tie and shirt, undershirt and pants.

Samantha pushed me down on the sofa and got on her knees before me. She shimmied down her dress and reached behind her back and undid her bra. I licked my lips as I looked at her protruding nipples.

"God you are gorgeous!" I told her.

She smiled and placed my hands on her nipples.

I began to pinch and pull on her nipples and she moaned and closed her eyes. Her hand going down between her legs. I followed her hand with my own and she moved my hand back up to her tits.

"Not yet big guy. Soon. I promise." She told me quietly.

I was curious but horny too and it was my turn to sigh as she diddled herself with her left hand and stroked my cock with her right while I played roughly with her nipples.

I got close to having an orgasm twice but she seemed to sense this and slowed down her rhythm just enough to keep me on the edge without going over the side.

Samantha then pulled up her dress from below and removed her black thong panties and pressed them into my face. Her juices were smeared on the crotch and I inhaled her fragrant scent.

"God, I so want to be inside you Samantha." I told her lustfully.

"I want you too John, but I'm not sure that your huge dick will fit in my little pussy." She said quietly.

"It will fit. I'll be gentle and go slow. You trust me don't you Sam?" I told her.

"Yes. Mmmm. Okay. Just do it in the doggie position. Okay?" She asked.

Samantha bent forward and I got behind her. I have only had doggie sex a few times and none of those times were very coordinated. But she was so tiny and I parted her ass cheeks and slid a finger inside her pussy. God she was wet. I inserted a second finger and finally a third finger.

"Oh John!" She groaned.

I removed my fingers and wiped her juices on the head of my dick. I put the head against her pussy entrance and pushed and my large bulbous head slid into her pussy.

"STOP!!! JUST STOP!!!" Sam reached back and pressed her hand against my stomach.

The look on her face showed how terrified she was and also how turned on she had become.

"Slow now John. Push it in slowly. Oh my fucking God your dick is massive. Oh fuck, oh fuck, oh fuck." She almost cried as I slid my length into her cunt.

I kept pushing inside her tight little cooze until my balls were against her pussy lips. I grabbed her hips and slowly withdrew until just my dickhead was wedged inside her pussy and then pushed inside her again.

"Oh fuck, oh fuck, oh fuck! Your dick feels so amazing John." She told me.

I pulled back out to my cock head and then pushed in again. Out and then in again. Out and then in a little faster.

Samantha looked back at me and with lust etched on her face. She mouthed the words "Harder."

I pulled out and slammed in fast and hard.

"Yes!" She squealed.

Out and then in, out and then in, out and then in.

Samantha looked back at me and said, "Fuck me John. Harder. Harder! Harder!! Harder!!! HARDER DAMN YOU!!!"

I was ramming my erect cock deep and hard into her cunt and I was so beyond ready to cum and she beat me to it moments ahead of me.

"YES, YES, YESSSSSS I'M CUMMMIIINNNGGG!!!!!" She cried out.

I drove in deep and grunted, "Fuck yeah!" And began to spurt huge thick globs of cum deep inside of her cunt.

It was the most intense orgasm of my life and I collapsed on her back, totally out of breath.

I rolled on my side with my dick still deep in her pussy and we both were breathing heavy.

"That was so incredible John. Thank you. Thank you. I so needed that. Oh God." She gushed.

I sniffed her hair and grabbed a handful of her breasts and whispered, "I love you Sam. And then fell asleep.

Samantha was gone when I woke up a couple hours later. She left me a note that said, "Thank you for the lovely evening. It was the best sex EVER! - kisses, Sam"

****

I got up the next morning and found her tiny panties wedged in the cushions of my couch. I brought them to my face and inhaled her fragrant pussy, but I also picked up another smell that I couldn't place. I dismissed the thought and tossed her panties on my bed.

I took a shower and got dressed for work. I was whistling as I drove to the market to gab a coffee and who did I run into? Yep. Samantha.

"Hey you! You left before I could thank you for such a lovely evening last night." I told her.

Sam wasn't smiling. Uh oh, was I not supposed to cum in her? I panicked and seeing the look on my face she touched my arm and said, "You did nothing wrong John. It's me. I'm sorry. It's just not going to workout with us. I-I." And then she started to cry. Right there in the store.

I pulled her to me and held her.

Sam stopped crying and looked at me. "Is there someplace we can talk less public?"

We walked out to my car and got in.

"I'm not what you think I, who you think I am. You won't understand. Trust me. It's just better this way for both of us." She said quietly.

"I don't follow you Sam. Are you upset that I told you that I loved you after we made love. Were you not as affected as I was? Our joining was not by mistake. It was fate. I've never connected with a woman like I connected with you last night." I told her.

"Really John? You mean that? You're not just telling me that to get me to have sex with you again?" She asked with pleading eyes.

"I love you Sam. I do. What we did last night was so incredible that I don't have the words to describe it. I want you to move in with me. I want to buy you presents and give you pretty flowers and travel with you." I gushed.

I couldn't help it. I was smitten.

I called in sick to work. Something that I've never done before and I took Samantha back to my house and we made love together.

I tried to go down on her and give her oral pleasure but she fought my advances every time. She said that she didn't like that so I relented. I moved on top of her and tried to take her in the missionary position but she turned around and I entered her pussy in the doggie position again.

Okay, there were some walls that needed to come down before we could get there. I was willing to work with her on that. I should have seen the doggie position as a red flag that it was something more serious but I was so in love with her that I didn't make a scene about it.

****

Sam moved in later that week and we began to share everything together. I bought her some nice jewelry and a big bouquet of flowers every Friday. We made love every Saturday afternoon and she gave me a blowjob every Wednesday.

Our life was bliss until...

I saw her showering one Saturday morning. What a vision of beauty! I stroked myself hard as I watched her perfect apple ass through the shower door. Her long lean legs and the way her breasts showed on either side of her small back. I was going to enter the shower with her and fuck her silly, but then she turned around.

My Samantha, the woman I loved and gave my heart to. She had a dick.

I stopped stroking my cock as her eyes opened and looked at me. I slapped myself in the face and began to chastise myself for being so stupid and naïve.

I was mad. I was beyond mad. I was hurt.

Samantha stopped the shower and walked over to me. Her body dripping wet as she grabbed my arms. "John, John, JOHN!!! Look at me!" She urged me.

I sat down on the toilet and closed my eyes tight. "No, no no, NO! It's not real. This isn't happening!" I told myself.

Samantha tried to pull me up and I pushed her away. She was light as a feather and slipped on the tile floor and flung against the wall and crumbled to the floor. Fuck!

Sam didn't move for several minutes and then se stirred and mumbled, "I think my wrist is broken."

I took pity on her and went over to her and helped her up and we walked into the bedroom. She was shivering and I wrapped her in some blankets. I looked at her wrist and felt it and it didn't feel broken. I found an ace bandage and wrapped it for her and then went into the kitchen and made some hot tea for us both.

We sat on the couch in silence and sipped our tea. There was a big elephant in the room between us and the tension was so thick that you could have cut it with a knife.

I looked up at her and shook my head, "I can't believe you are a guy! How could I have been so stupid?"

"John, I'm not a guy." She said quietly.

"You have a fucking dick!" I yelled at her.

"Yes, I have a dick." She said in a whisper.

"I'm so fucking stupid for not having noticed sooner that I was actually fucking your asshole and not your pussy.! A fucking tranny and I fell for it. Hooray! The jokes on me! FUCK!!!" I raged.

"I understand that you are upset, but I'm not a transvestite John." She said quietly.

"What?" I asked.

"I said that I'm not a transvestite." She said again.

She looked at me and the moment the words left her mouth, tears began to stream down her cheeks. "I'm something much worse. I'm a hermaphrodite. A freak. And I'm sorry for not telling you sooner."

"A hermaphrodite? No fucking way. Show me." I said in disbelief.

"No. It doesn't matter anymore. You're not going to stay with me now. Not after this." Sam sobbed.

"Hey, hey. Shhhh. I'm sorry. I was acting like an ass. Shhh. Come here baby." I told her and wrapped my arms around her.

I held her close to me and thought about the possibilities of her body and oddly enough, I started to get aroused. And Sam felt it too.

I was still naked and my dick grew hard between us.

"John? Does this mean you forgive me?" She asked.

"I'm not sure what it means Sam. I'm still hurt but I'm no longer upset. I have questions. Lots of questions. Can we talk about your dick?" I asked her.

"Yeah, okay. What do you want to know?" She asked me.

"Well how does it work?" I questioned her.

"It mostly doesn't work. It just kind of hangs there inert." She told me.

"Okay. Can I see it?" I asked curiously.

"Okay." Sam said.

She unwrapped herself from the blankets and leaned back and her dick laid against her stomach.

"Can I touch it?" I asked.

"Uh-huh." She replied.

I moved my hands to her dick and touched it gingerly with my thumb and index finger.

"It feels spongy. I see that it is uncircumcised." I said.

I wrapped my hand around it and pulled the skin down from her glans and saw that the head was a dark purple. I released my hand and the skin rose up to cover the head again.

I let it down to her stomach again.

"I never touched another penis before. It was kind of neat." I smiled.

"Thanks for being gentle with it." She smiled at me.

"So how does it work? Do you pee out of it?" I asked.

"No. no urine comes out. The testes or balls were removed at birth so..." She began.

"You can't ejaculate?" I answered for her.

"No I can ejaculate it's just that no sperm comes out. It's mostly just a clear sticky fluid." She told me.

"Oh, okay. Do you jerk off when you are horny?" I asked.

"No, it only gets hard when I have anal sex with someone. Then I can jerk it until it explodes." She smiled sheepishly.

I was rock hard and placed Sam's good hand on my erection.

She looked at me and smiled and then leaned down and took my dick into her mouth. My dick produces a lot of precum and as she sucked me I could feel it rising up my shaft.

I was curious about her penis and reached my hand down to her crotch and started to run my fingers over it.

Sam stopped sucking me long enough to see what I was up to. She leaned back and brought my head down to her crotch. I had never done this before but was curious just the same. I held her spongy dick in my hand and stroked it up and down. I the moved my lips against the sides and started to suck it gently. I moved it down to the side and took it into my mouth.

"Mmmm," I sucked it into my mouth.

I removed it and pulled down the skin covering the glans and began to suck it in my mouth again.

"Careful John. The head is really sensitive. That's better. Swirl your tongue around the crown. Mmmm. That feels nice!" Sam cooed.