My Life with Tess McGregor Ch. 02

Ch. 02 Tess Is Happy To Pop Brad's Cherry

Sunday morning I would normally find myself alone in bed. This morning I found Tess spooning against me. When she discovered that I was awake, she wiggled her butt on me. My arm was already draped over her body and she had pulled my hand to rest over her breasts. I kissed her neck. Then, I scooted over so she could lay on her back. I looked at her and stroked the hair away from her face.

"Tess, I know this is very sudden and things are moving pretty fast, but... I'm infatuated with you. I'm very attracted to you. We've only known each other a short time, but I feel close to you. I feel like I've known you for a long time."

I looked at her face and she was biting her lip. Her eyes looked like a puppy. She had her hands clasped under her chin. She was quiet.

"Uh-oh. I said too much."

"No. No, you didn't. I'm just trying to find the words. It HAS been going fast and I don't want to say something that we both might regret."

"Like what?"

"Well, like LOVE and FOREVER; those words that come to mind during a new and exciting relationship. We've only know each other for a few weeks and already those words are banging around inside my head."

"I'm so glad you said that. Not that I'm afraid of love. And, if it's the right person, then... forever might not be long enough."

"Oh, my sweet man. You know just what to say. I think this is going great, and so far, I don't want it to end."

"Ok, let me disappoint you right off the bat... I've been wanting to ask... what is your age?"

Tess giggled and said, "You're so silly. I'm twenty-five... How old are you?"

"I'm thirty-four."

She reached up and kissed me. She caressed my face and looked at me with contentment and happiness. Those beautiful eyes telling me, 'If you want me, I'm yours.'

"Well, let's agree to take it... I don't want to say 'slow,' but, without being afraid to move forward, we should use caution. There's a lot yet to discover about each other. I want to tell you all about me. Where I've been, what my goals are. Who I know. What I know."

"You're so smart... I feel the same. We can keep doing what we're doing, but let's not spoil it with jealousy and ego." Tess said with a maturity I hadn't expected from a twenty-five your old.

"I like the sound of that?" Just then my stomach growled.

"How did you like the sound of that?" We both busted up laughing and she rubbed my belly.

Then, I asked, "Want to go out for breakfast?"

"Oh, please... I'm fucking starving!"

"Alright, let's get ready."

At breakfast, we were sat at a large booth. Tess scooted over close to me and I got a thrill feeling her body close to mine. She looked good and that was confirmed by the stares coming from several of the men in the restaurant.

She wore a skort with platform sandals and a loose fitting top. I could see that she was wearing a bra. Her top wasn't exactly fully see-through, but it was sheer enough to make out her bra. Also, the bra couldn't keep her tits from letting me know they were there. Her brown hair cascaded in large waves around her face and just past her shoulders. She never seemed to wear a lot of makeup, just enough to highlight her delicate features. Tess had full lips and a cute nose. Her eyes shined a pretty green and her naturally long lashes accentuated their glint.

I was proud to be sitting with her. She snuggled up against my right side and playfully used her hands to touch me in a way that sent shivers down my spine. She was very distracting. I couldn't help it, my mind was busy thinking about her sweet voice as she looked at the menu and talked about what looked good and what she wanted to order.

She apparently had made her decision as she pushed the menu aside and wrapped both off her arms around my right bicep. Her face was close to my shoulder and she pulled my right hand over to rest on her left thigh.

"What are you going to get?" She asked while she was feeling my bicep.

"What... oh, umm. I haven't even looked yet." I said as I glanced down at her sweet face with her eyes looking up as if to say, 'Silly Brad, am I bothering you?'

"Well, here comes our server, you better hurry, because I want to order. I'm hungry."

"Ok, you go first."

After we ordered I moved my hand up her thigh, feeling her soft skin. I reached the small bulge at the top of her thighs and gave a little rub.

"Be careful, Honey, I don't wanna cause a scene if you give me an erection."

"Oh. Yeah, you're right. Sorry."

"That's ok. That's why I'm wearing a skort. It does a good job of hiding me without having to do a full tuck. But, still, sometimes if I get really excited, it has a tendency to show."

"OK... God, you make me want you so bad. You turn me on just sitting here."

"Hmmm, that's nice to hear. I confess, I feel the same about you. I love the way you're so turned on by my girl-cock. It makes me want you too... Here comes our food!"

After we ate, Tess moved back to snuggle up next to me.

"Hmmm, that was good. Their pancakes are delicious."

The whole time we were eating, I couldn't stop thinking about fucking her. When she snuggled up to me again, I put my hand back on her silky thigh.

Finally, I said in almost a whisper, "Tess, I think I wanna try... um... anal."

"Well, you already di... Oh... OH! I see."

She squeezed my arm and tried to get closer. I could tell this made her excited.

Tess moved her face close to mine and said, "I would love to be the one to pop your cherry, Brad." She giggled and I raised an eyebrow at her comment. Then I smiled as she said, "When we get home, let's change into something comfortable at my place."

On the drive back to the apartment, Tess sat close to me. Her hands were busy rubbing my cock the whole time. After we parked in the garage and I turned off the motor, we kissed while she continued to rub my cock through my pants.

I broke away and said, "Fuck, Tess, you're incredible. I still can't believe this is happening."

"What do you mean?"

"Well, I'm going to be brutally honest here... never in my life did I imagine that I would be so taken with and attracted to a transgender girl." She ran her fingernail across my cheek and squeezed my cock. "I'm not gay. I'm not attracted to men. I'm just not into that. But, you... you're the unexpected surprise. I can't get you off of my mind. I may be obsessed with you and I hope that isn't a bad thing."

"Oh, Brad. I'm so glad to hear you say that. I would never want to appear clingy either, but... you turn me on so much. You're unlike any man I've ever met. I know it's early in our relationship, but I can't help myself... I'm falling in love with you."

I squeezed her and kissed her deeply. Tess didn't need to hear my reply. At that moment, our kiss told her that I felt the same for her. We hugged tightly as I felt her sweet breath on my neck.

When we got out of the car, I joked, "I'll just pole-vault to my place and grab a change of clothes." I showed her the long lump of my cock making a rude bulge down the leg of my pants.

She giggled and ran ahead of me. This was good as it more than likely distracted anyone who might be around from seeing my condition.

When I entered her apartment, Tess was back in her bedroom. I hollered out that I was here.

"Ok, I'll be out in a minute."

I had changed into a pair of thin workout shorts and a T-shirt. This was acceptable attire in the warm California weather.

When Tess walked into the living room, I was sitting on the couch. She was wearing a frilly, see-through pink camisole with matching panties. My eyes popped out of my head. When she saw my reaction, she giggled and spun around.

"What do you think?"

"Come here and turn around." I wanted see her perky, round butt in those panties.

Tess bent over slightly, giving me a face-level view of her see-through panties. I reached up and felt her ass, rubbing around her butt and thighs. I put several kisses around her butt. I then pulled the panties up into the crack of her ass cheeks, giving me more skin to kiss and feel.

"Oh, Brad, you're making me hard." I reached up between her legs and felt the lump I had made. She was growing and her cock was snaking up inside the front see-through gusset of her pink panties. I rubbed it and then turned her around to face me.

"Fuck, Tess, you're driving me wild with lust." Her cock was teasing the top hem of her panties. The head of her cock was pushing up and up until it finally broke free and extended past her panties. It throbbed against the material and I leaned forward to lick the underside of her pretty cock.

"Hmmm, Honey, that's so fucking sexy. I love the way you worship my cock."

I slowly pulled her panties down just a little to expose more of her shaft. Her panties cradled her cock so that it stuck up and out towards my face. I let the tip of her cock touch my lips. I wet my lips and Tess pushed forward just enough to let the tip enter my mouth. I used my lips to play with her pink crown. I didn't go down on it, I wanted to tease her. I let my lips roll around the spongy, pink head.

"Oh, God, Brad. You know just how to tease a girl."

I grabbed both of her ass cheeks and used my grip to pull and push the head of her hard cock in and out of my mouth. Tess was sighing and moaning at the pleasure I was giving her.

I moved my mouth off the end of her cock and ran my tongue down her exposed shaft. This made Tess twitch at the sudden feeling. She was shaking. Up and down, my tongue raked along her length, causing more of her cock to escape over the top of her panties.

When I reached her crown again, I let her cock enter my mouth. I slowly let more and more slide past my lips, until her entire length was in my mouth. While I sucked her cock in and out, I used my tongue to glide under her hardness.

Just then, Tess grabbed my head and sighed with breathless expectation, "I'm gonna cum, Honey. You're going to make me cum, Brad. Oh, fuck, I'm cumming."

I had previously thought about this moment; Whether or not I was ready to take the cum-plunge. I'd never tasted cum before, but now, I wanted to taste hers.

I kept my mouth around her and allowed her to let loose the cum she was going to give me. I almost gagged as the first round of cum hit the back of my throat. It was warm and it tasted semi-sweet. I didn't mind. More cum entered my mouth and added lubrication to her throbbing cock as she pumped it back and forth in my mouth. I couldn't hold it all in as some escaped outside the corners of my mouth.

I looked up and saw her in the throws of a powerful orgasm. I could see her hands reach out to grasp my head and her tits wobbling inside her see-through cami. It was a beautiful sight and it made my cock hard to see it.

I actually enjoyed the feeling of her loaded cock exploding inside my mouth. I kept it in as long as she was cumming. I could tell she was done when she pulled out and sighed. Some of her cum still dribbled out onto my chin as I licked and cleaned the head of her spent cock.

"My, God, Honey, that was fucking incredible. You're a natural, baby. That was the best blowjob I've ever had."

"It didn't take long for you to get there either." I said, somewhat surprised that she was able to cum so quickly.

"It's all that teasing you did. Dang, you're so good at that. And, you swallowed all my cum too, Honey. I'm so proud of you."

"I did. And I liked it too. I'm glad you enjoyed it." As I said this, Tess pushed me back into the couch and climbed up to straddle my lap.

"Oh, look who has a hard one!" She reached down to pull my stiff dick from my shorts before settling into a sitting position.

Tess stroked my cock as we kissed. She used her tongue to clean off some of her cum that was still on my chin.

"Hey, I know you want me to fuck you, but I need this big, hard cock up my ass RIGHT NOW."

With that, she managed to pull my shorts off and toss them to the floor. She kept her panties on and I silently thanked her for that. I love how her cock looked in those shear panties. It turned me on so much.

I moved my hand to her ass, pulled her panties aside and searched for her asshole. When I found it, Tess cooed. I wiggled my middle finger inside and found no resistance. Tess was stroking my cock and kissing my neck. When I put another finger in her ass, she jumped and squealed with delight.

After I pumped my two fingers in and out a few times, I removed them just as Tess sat up and moved forward just enough to allow my cock to get into position at her pink hole.

She reached down to guide it in. She let go of my shaft and slowly sat down, breathing a sexy sigh as most of my cock was now in her ass.

I grasped her hips and started to move up and down. She remained still as I pumped in and out. Her head dropped and she began to move with me. Then, she looked up and leaned forward to kiss me. As we kissed, I reached for her breasts. My hand went up underneath her camisole and found her plump tits. Her nipples were hot and she squeaked as I pinched her hard nubs.

Then the most amazing thing happened. I felt her squeeze her sphincter around my cock. I thought I was going to explode, it felt so good. She had good timing, as I drove my cock in, she would relax. Then, on my way out, she tightened her sphincter muscles around my hardness.

I was in heaven. The feeling was like nothing I've felt before. I made a mental note to remember this when Tess was fucking me. Oh, how glorious this was to me.

Tess started bouncing up and down at a quicker pace. This spelled the end for me as I couldn't hold back.

"Oh, sorry Tess, you're gonna make me cum again!"

"Oh, yes, Baby, cum in my ass. Cum for me, Brad!" When she said 'Cum for me, Brad.' I exploded inside her. I pumped her ass without thought that I might hurt her. Using both of my hands under her ass, I was lifting her up and down on my cock.

Tess was thrashing on my cock. "Oh, Fuck, Brad. Fuck me! Oh, fuck! Fuck me!"

I wasn't hurting her, she was getting off on the pounding I was giving her ass. The feeling of my cum filling her was causing my orgasm to last longer than any other time. I kept pumping in and out. I never wanted to stop.

Tess finally slumped down on my cock and laid her head on my shoulder. She was panting heavily and I could feel her ass tremble as my deflating cock remained inside.

When she regained her strength, she looked up at me with wonder in her eyes.

"Oh, my God, Brad. I've never been fucked like that. Wow. This is good. This is better than anything..." She trailed off, not having the words to continue.

"Oooh, Tess. That was amazing. The way you squeezed my cock with your ass. Fuck! I've never felt anything like that."

We kissed as she wiggled her ass off my limp cock. With her arms around my neck, we hugged and kissed for a long time.

I could feel her getting hard again. Her cock was starting to bounce on my belly. She pulled back and reached down to stroke her semi-hard cock. Then, she looked up at me and said, "I need a break."

"Me too. Let's get something to drink."

Tess ran to her bathroom and I pulled my shorts on and walked into the kitchen to look inside the fridge. I saw a pitcher of iced tea, so I grabbed two tall glasses from her cupboard and filled them with ice. Tess came walking in just as I was pouring the tea.

"Oh, tea sounds good. Thanks, Honey."

"You're welcome... my Love." Tess jerked her head up in surprise when I said that. She almost spit her first gulp of tea all over the kitchen.

"I know. I said it. Now it's out there... But, I meant it. I'm falling for you in a big way. And I don't care. I want this."

"You want this?" She said as she jokingly flourished her hand down her body like Carol Merrill on Let's Make A Deal.

"Nooo. I mean, yes!... I mean... I want you."

"Oh, Brad... you're saying all the right things to make me want you too... And I do... I want you too!"

We both set our glasses on the counter and she jumped up in my arms while wrapping her legs around my middle. As we hugged, I said, "I just hope it's not just infatuation that will fade away after a few months."

"Don't say that." Tess scolded me.

"Well, I want you to know, I don't have a lot of experience with relationships. I got married at an early age. Then, it went south because she couldn't put down the bottle. That was just last year and since then, I've only had a few dates. Nothing like this."

"How is that possible?" Tess asked. "You're a very handsome man with a sexy body. Plus, you're very respectful and kind. That's what I love most about you, by the way."

"I'm not a prowler, I guess. I don't cruise the bars to pickup chicks. I never joined a dating site. I don't know... that's just how it is."

"Hmmm, I see. Well, I'm lucky to have found you just in time." She kissed me. With my hands under her ass, I hoisted her up to kiss her back.

Tess pulled away and said, "I want a snack." I raised my eyebrows and tilted my head sideways in jest.

"No. Not that. Not right this minute, anyway... Let's see what I've got in the pantry."

She jumped down off of me and went to the pantry to pull out some bags of crackers and we sat and munched on those with our tea.

"You know, you should come by the boutique sometime. You should see the things we sell."

"Oh yeah? Like what?"

"Well, this outfit, for example. We sell things like this and other sexy wear. We also sell dildos and sex toys."

"Do you wear that outfit at work?"

"Sometimes... If I'm feeling naughty." Tess bit her little finger after she said that and smiled at me with a mischievous look on her face. Then she continued, "I have to wear pasties though... it's too shear to wear in front of customers."

"I bet some people wouldn't mind." Thinking that I would love to see her out in public wearing this outfit.

"That's for sure. Sometimes we get creeps who come in looking for a cheap thrill."

"Ughh."

"Right... I'm just glad we have a bouncer who protects us from those weirdos."

I scooted my chair closer to Tess. I put my hand on her thigh and rubbed her silky skin. She smiled at me but didn't move. I ran my hand up her thighs and touched the bump her coiled up cock made in her panties. She flinched, but still didn't move.

I rocked a finger back and forth against her growing bulge. My little trick worked. I wanted to get her going and it didn't take much to accomplish. Her panties began to expand. Her bulge became more pronounced. Tess shifted a little in her seat to give her growing erection some room.

I looked down to see her cock pressing against her panties. I told her to stand up. She complied and stood right in front of me while I sat at in my chair. This was going to be a near repeat performance from earlier. I absolutely love the way her cock looks in those panties.

I raised my hands up to the strings of her panties at her hips. I toyed with the strings. Pulling them down just a little, then back up. I could see her cock was straining to be released. It was very hard, but trapped at an angle inside her panties. It looked incredibly sexy in that position. I reveled in its beauty.

"Jesus, Brad... you sure know how to make a girl feel sexy."

I wanted very much to tease her again. I wanted it to last. I wanted to suck her cock real bad. It was teasing me as much as it was teasing Tess. But, we had to wait.

I ran my fingers just under the bottom hem of her panties. My fingers barely grazing the side and length of her cock. It twitched and she sighed, "Oh, fuck, Brad... you're driving me crazy."

I continued to pull and caress the hem of her panties, making it tug on her rigid cock, causing it to move inside without being touched.

"Oh, my God. I can't believe how much of a tease you are... Ohhh, that's so sexy." She said looking down at me while she squeezed her large breasts.