My Life with Tess McGregor Ch. 01

But, I couldn't erase the fact that she was also very feminine and soft. Her legs and arms were not that of a man. Definitely not masculine. What I could make out, her tits looked incredible and her curvaceous body looked soft and supple. Her voice was pleasantly feminine. Not gruff or "dark brown," like Lola from the Kinks song.

Still, there was something...

Then I thought, 'Could she be packing a piece?' I've never considered myself to be bi-sexual. I've had thoughts, but always discounted any idea of a sexual relationship with another man. But this was different. SHE was different. Tess was most definitely intriguing.

I got online and did a search for transgender girls and found T-Girls and She-males. What I saw ran the gamut. From bad, to good, to REALLY good. Some of the t-girls were incredible looking, beautiful, in fact. The really hot ones appeared fully female except for the obvious appendage.

I began to think of Tess having a cock. Did she have one? Would I ever get the chance to find out?

My cock was hard just thinking of Tess having a beautiful cock like some of the t-girl cocks I saw online. I rubbed one out looking at the online images of the pretty t-girls and imagined Tess as one of them. I was infatuated and couldn't stop thinking about her.

The week went on without much interaction with Tess. I heard her friend Nataly come over again, but nothing brewed.

Then, on the next Saturday, the landlady, Nancy, and her boyfriend, Chuck, put on a little meet-n-greet by the pool. Chuck was smoking some ribs and chicken and they had tables set up with some pot-luck dishes.

Around two o'clock in the afternoon, I decide to put on my trunks and made a drink. I headed out to the festivities where people were swimming and laying out on the deck enjoying the food and music.

"Hey, Brad!" Came a greeting from Nancy. "So glad you could join us."

"Hi Nancy... Yo, Chuck! Wow, those ribs are looking good, my friend."

"Thanks, bro, you ready for some?"

"Not just yet, but thanks." I held up my drink as if to say, I was gonna do some drinking and eat later.

"Well, don't wait too long. It may be all gone."

Just then, I saw Tess walking out of her apartment and she was heading my way. She was wearing a skimpy bikini top and a thin chiffon wrap around her hips. Her long legs were accentuated by the high heels she was wearing. 'FUCK, she looked good!'

I looked at Chuck who was watching her too. He looked at me with that bug-eyed look, and I knew what that meant.

Nancy saw her approach and said, "Hi Tess, so glad you could join us too. Have you met your next door neighbor, Brad?"

"I sure have. He helped me move in."

"Ah-ha, well, isn't that nice of him?" Nancy looked at me and winked.

"I sure needed the help and he was in the right place at the right time."

"Aw, it was nothing anyone else would have done to help out a neighbor." I finally said, smiling at Tess.

Tess looked at me with those bright green eyes. Her smile was so lovely, it made me melt. She batted her eyes and put her hand on my arm. I continued to melt. God I wanted her. I wanted to find out what she had.

Nancy spoke up, "Tess, would you like a drink? We have beer and soda, and there's some water, if you like."

Tess looked at the drink in my hand and asked, "What are you drinking, Brad?"

"Um, yeah, uhh." What an idiot. I couldn't think straight (no pun intended), so I took a sip to remind myself what the fuck I had made. "Ahhh, it's a Mint Julep. Only I leave out the simple syrup and just add the mint leaves. So, it's really just a Bourbon and mint cocktail."

"That sounds wonderful!" Tess said as she again squeezed my arm.

"Would you like a sip?"

"I would. thank you." I handed her my glass and watched as Tess put the glass to her lips. I could see the amber liquid hit her beautiful painted lips as she sipped.

"Hmm, that's tasty. I'd love one of these."

"I'll make you one. Be right back."

I hurried back to my apartment and made her cocktail. When I got back, Tess was sitting on a lounge chair and talking with Chrissy, one of the other female tenants. When I got close, they saw me approach. They both giggled and stopped whatever conversation they were having.

I handed the drink to Tess and she took a sip. "Oooh, that's good, Brad. I approve." She looked at Chrissy and again, they both giggled.

I walked over to where Chuck was manning the bar-b-cue and struck up a meaningless conversation all while thinking about Tess and her long legs in those sexy high heels. I saw other guys checking her out too. I looked over at her and she was looking right at me over the rim of her glass. Her eyes smoldered with sex. I couldn't hear what the hell Chuck was talking about.

"Uh-huh, yeah." I said, not paying attention to him.

"Ok, Brad, it was nice talking at you." Chuck said in a humorous way.

"I'm sorry, Chuck. What did you say?"

"It doesn't matter. I can see you have your mind on other things." As he nodded towards Tess.

"Uhm, uh, yeah. Sorry." I looked at Chuck and almost said, 'Isn't she fucking hot?' But decided that would be bad form.

Instead, I put my drink down on a table next to Tess and walked over to the pool. There were only a couple of people in the pool, so I jumped in to cool off and clear my mind. I stayed in for a few minutes and then climbed the short stairs to the deck where Tess and Chrissy were sitting.

The cool water distracted me from the fact that I had a semi-hard on. When I got out of the pool, it showed. My trunks had become plastered to the contours of my half-hard cock.

I looked up at Tess and she was looking right at my trunks. So was Chrissy.

"I like those trunks, Brad." She said as Chrissy gave Tess's hand a light slap.

I blushed and tried unsuccessfully to hide my condition. So, I quickly sat down on the end of the lounge chair Tess was sitting on. This helped to hide my erection, but it didn't stop the teasing from the girls.

"You sure look like you're enjoying yourself, Brad." Chrissy said. This time Tess gave Chrissy's hand a little slap.

"Aww, be easy on him, Chrissy. What's a man to do with all this female skin showing everywhere?"

Chrissy was a hot little babe. She was close to my age and single. But, she had a boyfriend, who I noticed, was not here at the moment.

"Where's Greg, Chrissy?"

"That asshole? Who the hell knows? And I don't care." She said, followed by a large gulp of her beer.

"Chrissy was just telling me that her boyfriend got a job in another city and didn't bother telling anyone." Tess chimed in.

Chrissy added, "Good riddance. He doesn't know how to treat a woman. That bastard!"

Then Tess said something that kind of surprised me, "Brad here is pretty handy around the house, Chrissy. I'm sure he'd be happy to help you out with any CHORES you might have." Her emphasis on the word, 'chores' didn't go unnoticed by Chrissy, who had a head start on the alcohol consumption for the day.

"Oh, I'll have to remember that, Tess." They both giggled as Chrissy looked me up and down.

I grabbed my towel and was patting myself dry when Tess held up her glass and said, "Brad, honey, I finished my drink. Can I get another one?"

She called me, "Honey." I loved that. although she called other people Honey, it was the way she referred to me that made the difference.

"Sure thing, Tess. I'll be right back... Chrissy?" I offered to get one for Chrissy too, but she declined.

"You know, I think I'll go with you. I wanna see how you're making these tasty cocktails." I offered my hand as Tess pulled herself up from the lounge chair. "Thank you, sweetie."

As we walked back to my apartment, I couldn't help noticing Nancy and Chuck both watching us. So, I said out loud, "Be back in a bit, folks. I'm just gonna freshen up our drinks."

The sound of Tess's heels clicking on the concrete was sexy as hell. I don't know why. Just the way heels sound on a hard surface and the rhythm of her sexy strut. My cock was beginning to swell again as we entered my apartment.

Tess stood next to me in the kitchen as I made our drinks. She sidled up to me, allowing her breasts to brush up against my left arm. Both of her boobs looked mouth-watering. I tried not to stare as the movement she was making on my arm was sending signals to my crotch.

She then ran a fingernail around my bare shoulder, making little circles while she watched me fix our drinks. It was distracting, but I managed to complete the task without spilling anything. Then, she moved closer and whispered in my ear, "I can't stop thinking about the way your trunks looked when you got out of the pool a minute ago."

Oh, fuck, the way she said that sent chills up my spine and blood surging to my hardening tent pole. I slowly turned my head and we looked eye to eye. She had a smoldering look of sex in her eyes. She moved closer and our lips met for the first time in a tender kiss.

I turned my body to face her and put my hands on her hips. She threw her arms around my neck and our kiss became more urgent. I could feel my erection push against her. I'm sure she could feel it too.

I felt something else too. I knew what it was and I started shaking with nervous energy. I almost couldn't control my breathing, so I took a big breath of air to calm myself.

"Are you alright, Brad?"

"Yeah, I guess I'm just a little nervous."

"Well, don't be, Honey. There's nothing to be nervous about. It's just you and me here and no one can bother us." After a little pause, she continued, "I think now's a good time to tell you a little more about who and what I am."

With my hands on her hips, I pulled her closer to me. I could feel a lump next to my growing erection. I moved her hips a little to feel more of what was making that lump and said, "Tess, you don't need to explain. I think I know exactly what you are and it's driving me crazy."

"Crazy in a good way?"

"Well, yes, I think so... or, I hope so. I've never been with anyone like you before. It's brand new, and it's all I can think about."

"You've been thinking about me?"

"Oh, God, yes. I wasn't sure at first, but now I know and I wanna know more."

"Oh, Honey, that's music to my ears." She looked up and we kissed. Her tongue doing a little dance across my lips, as our swollen cocks were doing a little dance of their own.

I wanted to see her and so I pulled away and stepped back just enough to see the thin chiffon wrap protruding out from her body. Her tuck had come undone and the swelling of her cock had pushed her banana hammock aside, allowing her cock to extend beyond its confines. The hard cock hidden from view was growing harder. I watched as it slowly lifted the chiffon wrap that was tied around her hips. Her hands were on my shoulders as I looked up to see her looking back at me for approval.

I leaned forward to kiss her again. Using the grip I had on her hips, I swayed her back and forth, causing our two excited cocks to ceremoniously rub together.

I stepped back again and watched as Tess's cock waved like a flagpole between us. Her wrap was tied on her left hip, exposing all of her left leg. A little coaxing and her cock would be out in the open air. I looked up at her and asked, "May I?"

"I thought you'd never ask." She said as she put her hands on her hips and stepped back a couple of inches.

I trembled with new excitement. Part of me felt like a teenager nervously navigating my first sexual experience. This was beyond that. It was taboo. It was against my norm; what I had grown accustomed to. And I was ready to make the jump. To plunge head first into the dark. To explore something I had never known or experienced before.

Still standing, I reached for the knot on her hip. I untied it and let the back part fall away. I kept hold of the front part of her wrap and slowly removed it. Tess's cock came into view. It bounced just slightly as I removed the wrap, showing me how proud and excited it was to be admired by someone with a newfound appreciation.

Her cock was beautiful. It matched her complexion. The pink crown and the milky white shaft was something to behold. I was intoxicated with lust for her body. Her long legs. Her curvy hips and large, round breasts was a package made complete by the sexy-as-fuck cock looking up at me, asking for attention.

I tossed her wrap aside and reached out for her cock but stopped to look into her eyes. She saw my hesitation and said reassuringly, "Yes, Brad, you may touch it."

With my fingers extended out, palm up, I gently touched the underside of her cock. The skin was silky soft and taut. Tess flinched when my fingers slowly moved up and down the shaft. I stroked the length of her cock with just my fingertips as I looked at her face.

"Oh, Brad. That feels so good... You're so gentle and considerate."

My fingers crept down to the base of her cock and found her balls. They were tight. I tenderly felt their firmness and Tess emitted a lustful moan at the feeling of my fingers.

I wanted a closer look, so I knelt down. I saw just how pretty a cock can be. She was smooth everywhere. Totally shaven. It didn't even look like she needed to shave. Ever. No ruddiness. Not a masculine form. It was a feminine appendage. A woman's cock.

I reached up and started to remove her bikini bottom. I looked up at Tess before I did, and she nodded, yes. I slipped it down around her plump butt and let it drop to the floor. She lifted her feet, one at a time, and kicked it away.

I put my thumb and two fingers around the base of her shaft. It was the only other cock my hands had ever touched and I was in a surreal trance. A place I had never been before. A scary and almost mythical place. The peripheral view of the space around me turned into an otherworldly place that I didn't recognize, and I didn't care.

With my left hand holding the base of her shaft, I used just two fingers of my right hand to softly stroke her entire length. My left hand pulled gently on her skin, making her cock taut and shiny. I marveled at its beauty. It looked absolutely delicious.

"Oh, Honey. You got me worked up." Tess said as I was engrossed in my close inspection.

Somehow, I found myself on autopilot as I instinctively stuck out my tongue to taste her pretty, clean skin. I let my tongue drift around, feeling the soft skin and spongy head of her pretty cock.

I opened my mouth and wrapped my lips around the taut skin of her pink crown. Just letting it wallow in the clutches of my lips. I could feel the contours of her cock head as I moved my lips around the end of her female appendage. I heard Tess moan and put her hands on my head. She wanted me to take more and I obliged.

The feeling of her cock entering my mouth was glorious and frightening at the same time. Fireworks went off all around us. My heart was pounding in my chest. I wanted more of her inside my mouth. I slowly worked her cock deeper and deeper, until I couldn't take anymore without gagging.

I removed my hand and let her cock move in and out of my eager mouth with the help of Tess slowly rocking her hips to and fro.

"Oh. Ohhh, Brad. How do you know how to do that?" Tess was breathing heavily, moaning and sighing with lustful pleasure.

I thought about what she said. I suppose it's a simple fact; I'm doing what I would want someone to do to my hard cock.

I placed my hand around the base of her cock and let my tongue slide out of my mouth along her sensitive underside, while still slowly bobbing front to back on her hard pole. That's when Tess warned me, "Oh, Brad, you're gonna make me cum, Honey."

When I pulled her out, I pointed her cock up and to the side so that I could see the cum from her cock. A couple of strokes and her cock lurched in my hand. I watched as thick ropes of her girlcum launched into the air. Over my arm and onto the floor. Another went flying over my shoulder. I looked up to see Tess throw her head back and wail. I watched in awe as her cock jerked in my hand, splattering large loads in my general direction. I stroked and pulled on her cock until it was spent.

Amazed at what I had just done and caused, I looked at the cock in my hands and the wreckage it caused.

I let go and stood up to grab a towel to clean up the wonderful mess we had made. Tess turned and grabbed ahold of the kitchen counter to steady herself. She was leaning against the countertop with her arms locked straight. Her ass was sticking out and moving with the motion of her heavy panting. When I saw this, I grabbed her ass and began to massage its fine, round plumpness. I jerked my shorts down to the floor as my cock flipped up like a flagpole after being let loose from my shorts. It was rock hard and ready to experience a new world of pleasure.

Tess arched her back and stuck her ass out even further. With both hands, I spread her cheeks apart, exposing her little pink hole. She turned and looked over her shoulder at my exposed ramrod.

"Brad, please be gentle. I've never had one that big in my ass before. But, please... please fuck me."

I spat on her asshole and on my cock. I rubbed my cock head against her ass, making Tess whine like a woman in heat. I nuzzled the head of my cock against her hole and started to press forward. I delivered another mouthful of spit onto our nexus. It provided enough lubrication to allow the head of my cock to push past her sphincter.

I looked down and saw the awesome sight of my rigid pole entering her forbidden hole. I massaged her ass and began to slowly move in and out. Tess laid her chest on the countertop and braced herself for my full invasion. I began to move more urgently and pressed deeper inside her.

Soon, I was pounding in and out of her ass, making her shriek and tremble. My hands firmly massaged her ass while Tess wriggled and pushed her ass back onto my rod.

"Goddamn, Tess, I can't believe I'm doing this. You're gonna make me cum so hard."

"Honey, fuck me, fuck me hard. Cum in my ass!"

That's just what I did. I buried my cock to the hilt in her ass just as it started to lurch and pump my cum.

Tess was wailing and thrashing around my cock as it unloaded blast after blast. I shook with a powerful orgasm as I slowly moved an inch or two of my cock in and out while I was still cumming. Her walls were like velvet around my hard spurting cock.

My legs went weak and I had to let go of her ass cheeks so I could steady myself by grabbing the countertop on either side of Tess's trembling body.

My cock felt so good buried in her ass. I let it stay there for a minute or two, and finally pulled out. This made Tess sigh and slump onto the countertop.

When we caught our breath, we cleaned up and stood facing each other. She threw her arms around my neck and we kissed.

"That was fucking incredible." I said as I pulled my face away from hers. She looked back at me with a smile of contentment and happiness. She was beautiful.

"Oh, Honey, you made me feel so good. Lord, I can't wait until we do that again."

Her comment surprised me just a little bit, but it was nice to hear.

"Mmm, I'll be ready. You make me feel so fucking horny, it's almost like a dream. I still can't believe I'm doing this... we're doing this... I mean..."

Tess interrupted me, "I know what you mean, Brad. I can only imagine what it must be like for you, being your first time. You were awesome, and just so you know, I'm horny for you too, baby. That was sooo naughty."

At that point, we decided to not go back to the party. We both needed a shower. I chased her as she ran to the bathroom. She was being playful and giggled as she did her best to escape my pursuit.

After we entered the bathroom, I turned the water on, then turned to find Tess standing there looking so adorable. I noticed she had the beginnings of an erection. While we waited for the water to get up to temperature, I grabbed her in a big hug and kissed her mouth. She threw her arms over my shoulders and jumped up into my arms. Her cock slapped my belly and her tits bumped up under my chin as she wrapped her legs around my middle.