You Dont Really Do Sexy

Disclaimer

Please note that this story is a work of fiction, nothing that happens or is said in this story occurred in real life. Any similarities to real-life events are purely coincidental. The celebrities featured act as fictional characters and their behaviours follow suit.

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You Don't Really Do Sexy

Starring Annie Hathaway

codes: MF, Cons, Oral, Cheat

Everyone around the table was laughing at the story I told about embarrassing myself in front of a sexy date. We were several bottles of wine into the night, and everyone was winding down before heading home. I was a little nervous at the start of the night; being the only single person there but everyone else made me feel at ease. Luckily, I was opposite Annie for most of it, and getting to look at the most beautiful person there for most of the night was a massive plus.

"That must have been embarrassing," Annie said as she reached for her coat. "Adam was always nervous when I turned up to our dates looking sexy."

"Well, not to sound offensive," I said, making the other three people at the table take a sharp breath. "You don't really do sexy."

"What do you mean?" She asked as she turned her head on an angle.

"Don't get me wrong, you're gorgeous, and we've seen you look pretty and cute."

"And the girls." The guy next to me added.

"And the girls. But I don't think we've ever seen you look sexy."

"Huh," Annie said, listening to me. "Luckily for you, my husband is calling me to go, but this isn't over."

Annie smiled before giving me a playful punch in the shoulder as she walked past me. We probably wouldn't be called friends, but we ran in the same circles and knew each other slightly. However, that comment could have gone wrong, but she seemed to play it like a joke.

The night ended quietly after Annie had left, and I returned home to my apartment as I expected to, alone. It wasn't too much of an issue for me as I had a date lined up for the next week. My plan until then was to work, exercise, and relax with a little bit of shopping.

****

Four days after the party, I was shopping for some clothes when my phone began to ring. It wasn't a saved number, so I almost ignored it, but something in the back of my mind told me to answer it.

"Ben, it's Annie. How are you?"

"I'm good, thanks, Annie. Just off doing a little bit of shopping."

"Oooh, anything nice?"

"Just some clothes, got a date next week and need to freshen up the wardrobe a little bit."

"A date? Nice. Get some boxer briefs. She'll appreciate them, and they always make it look bigger."

I felt this was a bit of a weird comment as we didn't know each other too well.

"Um... thanks. What can I help you with?"

"Well... look, I feel weird saying this but remember your comment at the end of the party a couple of nights ago?"

"Which one? About seeing the girls?"

"Oh no, everyone's seen my boobs. It's fine. The one about me not being sexy."

"I'm sorry about that. I'm not saying you can't be, just that we've not seen it."

"You don't have to apologise," Annie replied. "I'm not offended at all. I just feel I have to prove it."

"Prove it? To me?"

"No, more to myself. Meet me at Jardin Fleuri tonight at 9."

"Okay. I'll see you tonight." I replied, wondering if I'd just agreed to a date with a married woman.

****

I arrived at the French restaurant at about five past nine, and the maitre d'hotel showed me to the table. I looked around as we walked to the table, and the place looked upmarket but not completely fine dining. There was a bit of an edge to the place that I couldn't quite put my finger on. I wasn't over or underdressed for the place either, which was a pleasant surprise; my combination of cream chinos and purple shirt seemed to fit in with those around me.

I sat down at the table and perused the menu while waiting for Annie. I had expected her to be slightly late, which is why I left it until five past to arrive. The waitress started to make her way over the table when my phone vibrated with a text message. I looked at it to see it was Annie, I saved her number after the earlier call, and I expected her to cancel the dinner.

'I'm running late due to traffic. Can you order us a bottle of red, please?'

Before explaining that I knew nothing about wine, I showed the waitress and asked her to bring whatever was best. I waited on my own for several minutes before I saw Annie arrive. I was about to wave when she turned around, and I got to see how she was dressed. The actress walked over in a tight pair of black trousers and a black suit jacket, no bra or shirt underneath. Her cleavage was on full display and highlighted by a red tie. She smiled at my shocked face as she got to the table, the wine arriving seconds before, so the waitress poured two glasses before rushing away quickly.

"Nice to see you arrived early," Annie said as I stood up,

I leaned in and kissed her on the cheek, a friendly gesture between friends, but it felt like she hovered there slightly. I noticed that she wore barely any makeup. Her face was naturally pale with only a small amount of blusher and a bright red lipstick that seemed to match her tie. I pulled out her chair as a gentleman does, and Annie took a seat. It was also a cheap excuse to check out her ass as the trousers clung tightly to her curves. I moved across to my chair, and the brunette was already taking a sip of the red while looking over the menu in front of her.

"You look amazing."

"Thank you, I was dressing to impress. Adam was out of town, so I didn't need to explain why I'm dressed like this. Or why I needed some Dutch courage before coming out."

"Dutch courage?" I asked as I'd not heard the phrase before.

"I needed a drink before coming out like this. You may drop your eyes," she said with a giggle.

I looked down at her boobs as she gave permission and checked them out. They were big and looked great in the films but looked better in real life. They seemed to be flowing freely but held their place quite well; there didn't seem to be much drooping despite her being in her late 30's. I looked up at her and smiled to see the actress giggle.

"That is very brave, gotta hand it to you. God forbid a nipple popping out."

"Oh please, like I would risk it in public," Annie said before sneakily sliding the jacket to the side to show one of her breasts covered with a sparkly nipple pastie. "If this was a private dinner, maybe I'd risk it considering the company but not out in public like this."

"Considering the company?" I asked before drinking some of the wine, my nerves increasing.

"Well," she said before sipping her wine. "It's no secret you're easy on the eye Ben. It's a wonder you're single."

"I just don't think I've found the right woman."

"Or you've found too many. I spoke to Christine last night about you. It was part of the reason why I called."

"Christine? I never went on a date with Christine,"

"No, she said you were only compatible sexually. Maybe that's the problem."

"Sexual compatibility is a problem? I thought that would help with a relationship considering how much a couple should be fucking."

"Of course, but maybe some girls just want to go for dinner with you because they just want you for your dick," Annie said with a smile just as the waitress arrived, so I couldn't enquire more.

Just after ordering our food, Annie left the table to go to the toilet, and I was able to breathe for a moment, feeling as though the actress was sending out the feelers to see if I was interested. I don't think she needed to ask; who wouldn't be interested in her? Her body looked great. She was beautiful and had a great pair of legs, though they were covered by her trousers on this occasion. Though I think she had deliberately chosen them to show off her ass.

Almost as if it was planned, Annie arrived back just as the food did, and the conversation turned to a more dinner-appropriate subject of how our careers were going, and we were getting on well. It was much more akin to our interactions at the parties we've been to in the past but a one-on-one setting, so it was a lot more intense. The service was prompt, so it felt like the time flew by, and the desserts had arrived when I came back from the toilet. I had a simple chocolate cake while Annie went for churros. She looked me in the eye as I sat down before grabbing the pot of chocolate. I was about to say something when I saw Annie dip her little finger into the pot before bringing it to her lips and licking it off seductively.

I must've looked dumbstruck as she bit down on her lips. I felt a stirring in my chinos as she started to ooze sexiness; it was clear this is what she wanted to do all night but only had confidence after the glasses of wine and the restaurant had emptied a little bit.

"Tasty?" I asked.

"Very. Though I usually prefer cream, it goes down like a treat. I'm sure you're used to that."

"Haha, not as much as you'd think. This from Christine again?"

Annie nodded before pulling her phone out. She was scrolling through some messages before looking with a naughty smile on her face.

"Oh my god, I was on my knees, and it was like an explosion in my mouth. He warned me but I didn't expect that much. I didn't want to swallow so I just pulled it out, and he coated my face. It gave me a great glow." she said before putting the phone on the table.

"Yeah, I remember that. You gotta really hate swallowing to take it out and take a facial."

"A bit rude if you ask me."

"Should I ask you?" I said, looking at her.

Annie looked to the side for a moment before taking the pot of chocolate sauce. It was still a bit runny, so she poured it into her mouth before slamming the small ramekin onto the table. She took a large gulp and swallowed the contents before opening her mouth and showing it was empty of the chocolate sauce.

"I'm not rude."

I smiled at her show as I watched the actress slide her chair out and stand up.

"I've already paid the bill, so wanna go for a nightcap?"

****

We had barely left the restaurant before Annie grabbed my hand and pulled me into an alleyway. With her back against a wall, Annie pulled me close and pressed her lips against my own; my thoughts of her actions being playful flirting left my mind very quickly. Her tongue pierced my lips and soon massaged my own as her hands dropped down my belt. She made quick work of it as I looked around to see we were utterly alone. Our eyes locked again, and a smile came across her lips.

"Not a word to anyone." The actress said as she dropped to her knees.

"Not a word," I replied.

I watched as Annie undid and lowered my chinos coming up close with my erect cock. She rubbed the outline of my cock through the boxer briefs before rubbing her mouth along it.

"Good to see you took my advice."

She giggled slightly before grabbing the waistband and yanking them down my legs. My erection popped out and hit her in the face. She let out a 'wow' before grabbing it with her hand and jerking it to make me fully erect. As she did this, Annie leaned down to lick the tip and adjusted her head, so she was looking me in the eye as she did it. Her tongue rounded the head slowly before flicking the end in a quicker motion.

"Is this proving my sexiness?"

"That got reached when you walked into the restaurant," I replied as I watched her kneel straighter.

She took my cock and rubbed it along one of her breasts before letting it settle into her cleavage for a moment.

"Maybe I should show you how sexy I can be."

I silently nodded as Annie leaned forward and let my cock sink into her cleavage, giving me a slight tease of a tit wank. I was hoping it would progress more until Annie whipped it out and slid the head on my cock into her mouth. At first, she only took the head into her mouth, and I could feel the actress run her tongue around it. I looked down at Annie as her hand jerked along the length of my cock to ensure I could get the pleasure all along my penis. Annie repeated this for a couple of minutes before she dropped her hand down to my balls and started to give them a message.

"Fuck Annie, that feels so good," I said as I leaned my head back.

"You taste so good," Annie replied as she briefly took my cock out of her mouth.

I felt the actress rub my cock along her face before taking it into her mouth again and starting to bob her head up and down. I could see the actress take half of my length quite easily. Annie began to move further along my cock with a smooth motion, and I could feel her tongue massage the stem, my cock getting coated with her warm saliva throughout.

"God, Annie, your tongue feels amazing."

I could feel her giggle slightly as her head paused for a moment before she gave my cock a lot of suction. My eyes rolled into the back of my head from the pleasure as she sucked hard on my cock; her eyes popped up to match me as she took it out of her mouth and gave it a long lick before jerking my cock. Annie broke our look as her mouth moved down and licked across my balls. The combination of the jerking and the licking felt terrific, and it seemed like she was doing a professional job to get me off.

After a short lick on my balls, Annie moved her mouth back up to my cock and popped the head back in. Her tongue teased the eye as her hand jerked along the stem again. This time she increased the intensity of the blow job and kept her eyes on the job at hand. Her hand moved faster along my cock as she kept her tongue flicked along the eye of my cock. The speed increased to levels that I didn't think she could meet.

"I'm so close." I moaned as I felt her other hand move to my balls.

Annie massaged my balls with her hand moving in a circular motion against the smooth skin as her tongue followed the same pattern on the head of my cock. I leaned my head back and closed my eyes as I just enjoyed the feeling Annie was giving my cock. Her hard work was paying off as I felt my cock getting ready to cum. Her eyes looked up at me, and I nodded to show her I was ready. I was surprised as Annie released my cock from her mouth and stuck her tongue out, willing to take my cum.

Her hand jerked hard on my cock as the first shot of cum came out of my cock and landed perfectly on her tongue. I watched as more cum shot out of my cock, with some of it landing on her lips and by her nose. It didn't seem to put the actress off as she carried on jerking my cock until all of her cum had been milked out. Annie then closed her mouth and held her hand out. I took hold of it and helped her to her feet. She looked at me with a smile before opening her mouth to show it empty.

"As I said, I'm not rude. Should we get that nightcap at mine?"

"Yeah, let's do that," I said as I watched her walk ahead of me, her ass swaying from side to side with confidence.

I watched Annie throw something off the side before exiting the lane and turning to a vehicle. The actress climbed into the back of the Mercedes and left the door open for me to follow. I entered the car and closed the door before looking at Annie, who smiled at me.

"Tom, take me home, please."

****

I sat in the car as it pulled up to Annie's home. The lights were off, so it was confirmed when she said that she was home alone. The drive over had been more akin to the start of the evening when the two were having a pleasant conversation rather than the turn it took to the end. I looked over to Annie, smiling at him as she took her seat belt off.

"Last chance to escape. Stay in the car and go home or come and find out more about me."

Annie opened the car door, jumped out, and walked to her house. I exchanged a quick look with the driver before unbuckling and following the actress, catching up with her at the front door as she unlocked it. A smile came over Annie's face as she saw me in the reflection of the glass before she walked in and kicked her shoes off. I followed suit as I wasn't one to mess up a carpet and took my socks off with it. Taking them off is never sexy. I looked back up to see Annie leaning against a door frame.

"Hey, Ben."

"Hey, Annie."

"Looks like you made the right decision. Come here and bring your mouth."

I smiled as I walked over to the actress. She had turned, so her back was now against the wooden frame. My lips met hers as soon as I reached her, our tongues invading each other's mouths with passion as Annie's hands moved up my sides to my shoulders. The decision to forego a jacket made it easier for Annie as she rubbed her hands along my trapezius muscles before bringing them forward along my chest and undoing the buttons. She made short work of them as she was soon shuffling my shift off and rubbing her palms along my skin.

Her hands moved down my back before grabbing a good handful of my ass as she leaned her crotch forward and pressed it against my own. I could feel her hands start to move around to the front. I quickly grabbed them and moved her arms up against the door frame above her head. We shared a quick look before I moved my lips to her neck, pressing some soft kisses along it. A moan came from Annie as I moved across the front of her neck to the other side and continued the pattern. I looked up to Annie and saw that she had her eyes closed and her arms remained above her head despite no restraints.

"That feels nice." Annie moaned as I kissed around her neck.

"I got more places to visit," I replied as I started to move the kisses down her collarbone.

I looked up to see Anna giggle to herself as she watched my movements closely. From her collarbone, I was able to move to her chest and kiss the exposed skin on either side of her tie. My hands over up to the button holding her suit jacket closed and flicked it out, allowing the coat to open and expose more of her breasts. I opened the coat to see her breasts for the first time and was delighted to see she had forsaken the nipple pads. Instead of being covered, her nipples were in my eye line and were erect. I didn't want to rush, so I helped take the jacket off and continued kissing along her chest as I started to zero in on her nipples.

I took Annie's pink nipple into my mouth and gently sucked on it to cause a moan to come from the actress. My tongue circled the nub as it got covered in saliva, the actress enjoying the feel of my tongue on her as I could feel her knees start to go weak. She shuffled the jacket off her shoulders and let it drop to the floor. Her porcelain skin shone in the dimmed light of the room. Annie took hold of my head and moved me to her other nipple to repeat the process. Along with the licking, I bit down on the skin, causing Annie to take a sharp intake of breath.

"Take me," Annie whispered as I sucked hard on her nipple.

I looked up to Anne to see her eyes were filled with lust and desire. I stood back up and placed my lips on hers, allowing the brunette to start the kiss with passion. Her tongue thrashed against mine as her legs jumped up and wrapped around my waist. I placed my hands on her ass for support and started to walk into the kitchen. There didn't seem an easy way to navigate, so I placed her onto the countertop and put my hands on either side of her on the surface. As we continued the kiss, her delicate fingers worked their way along with the buttons of my shirt before running her nails along my chest.

I broke the kiss and watched as Annie licked her lips while looking over my body. Her hands went for my trousers, but I stopped her and undid hers instead. I grabbed her hem and underwear together and pulled them both down her legs to reveal her pussy with a small patch of hair resting above it. I threw her clothes to the side and pushed Annie back gently, so she rested on her elbow. Grabbing her right leg, I lifted it up and kissed along her thigh, causing a shiver to go through her body. I reached the top of her leg, and I could feel her left leg wrap around my back and pull me closer to her. Annie was clearly in no need of any more teasing. She wanted to get right to business.