Quite A Surprise From Annie

I woke up alone. Annie travelled back home to deal with a family emergency and Billy was away on a two week business trip. I did a video chat with Annie a few nights ago and we had a long distance phone call cum session that wasn't even close to what I wanted. She assured me that she'd be home soon to make it up to me, but I was like an addict in the midst of withdrawal.

I received a text from Billy not long after my call with Annie and he asked how I was doing without her.

"Horny," I replied.

He didn't respond right away and I went back to watching some crappy TV show. My phone dinged and my eyes bugged as I saw that Billy had texted me a photo of his hard cock with a nice bead of precum on the tip. My cock tingled and started to stiffen.

Another message came in shortly after and I realized that it was a video with his engorged cock head staring at me.

I pressed play and I could hear Billy's sexy voice, "Hey there, boy toy. Sorry that you have to be alone tonight. Maybe this might help you relax."

With that he started playing with his cock. Slowly milking it with precum oozing out with each upstroke.

"I want your tongue on my cock," he teased as he quickened his pace.

He was very vocal--moaning each time his hand moved over the tip of his dick and rubbing his juices onto the head. He was already in my mind as my hand moved to my cock--which was still moist from my session with Annie.

He was jacking himself hard now--telling me that he was getting close. I started to match his pace--I wanted to cum with him. He was moaning nonstop now while giving his big sweet dick a pounding. I could barely keep the image steady as I was right there with him. His moaning stopped suddenly as he held his breath and I could see the first shot of his hot cum burst from his piss slit. A shudder went through me and I could feel my own orgasm building from deep inside my balls. He kept cumming and as he aimed towards the camera, a glob of cum hit the lens. That was it for me and the first shot hit below my neck. I jerked down again hard and the second flew not far from the first.

"Yeah baby, cum for me," I heard him say on the video as I was drifting back from heaven.

I looked back at the video and he was on screen now licking his cum from his fingers.

"Can't wait to see you when I get back in about a week," he purred.

He licked his lips and puckered at the camera and that was it. All I could text back was--wow. He returned a laughing emoji and then he said that he was sorry but he had to go to bed to make an early morning meeting. I sighed and wished him a good night. I drifted off to sleep.

The alarm went off and I woke up with dried cum all over me. I got myself into the shower and made it into work. I still had another week to go before Billy got back and who knows when Annie was coming home. As quitting time was almost there, I got a text from Annie. She said that she felt bad for me and she wanted to have a virtual cocktail hour with me. She gave me the address of a bar that she knew of that would be quiet enough to have a video chat and told me to be there at 6:00--sharp. I didn't think that it was that great of an idea, but at least it would get me out of the house and I could see her and have a nice chat and a drink or three.

Six o'clock and here I was trying to find this place. I found the address, but not the bar. All there was is a black door and black painted windows. I pulled on the door handle and it was locked. I texted Annie and told her that I was here, but the place appeared to be closed. She texted back quickly telling me to ring the bell and say that she sent me. I found a painted over doorbell button and pushed it. The door cracked open and a well dressed attractive woman asked if she could help me. I told her Annie sent me and she immediately welcomed me in. The door closed and she bolted it behind me.

"This way, please," she said as she led me through thick red velvet curtains.

Any unease I felt about the cloak and dagger treatment quickly subsided as I walked through the curtains into a small, cozy bar. It was about maybe 800 sq. ft., and very Victorian looking with a lot of wood paneling, crown moulding, dark red velvet drapery--very warm and welcoming. There was an eight seat bar with large dark red leather booths around it, mostly lit by candlelight on the tables and bar lights. We were the only two people in the place so far.

She directed me to a booth that had a RESERVED placard on the table. I chuckled to myself (reserved? really?).

"What can I bring you to drink?" she asked as I slid into the horseshoe-shaped booth.

"Ahh...how about a nice Cognac?" I replied.

She gave a sexy smirk and headed to the bar--I guess she's the bartender as well as the hostess.

My phone buzzed and it was Annie on video. I answered and there was her cute, smiling face filling the frame.

"Hey baby. I miss you," she started off.

"Here you are my dear--a 'nice' Cognac," the bartender said as she interrupted before I could respond to her.

"Who's that?" Annie asked.

At a loss as I didn't know her name I said, "Actually, I'm not quite sure yet--my name is Dan...what's your name?"

Realizing that she was interrupting, she smiled shyly and said, "Hi, I'm Sasha."

"Ah," I said playfully overacting into the phone's camera, "this is...Sasha." I turned the phone so she could see her.

"Hey there, beautiful. Are you taking good care of my man?" Annie replied.

"Well we just met, but I brought him his first drink, so I guess we'll have to see where it goes from here," Sasha quipped as her eyes drifted up from the screen and locked on me and scanned me from head to toe.

"Get back to your bar you little slut--I'll see you later," Annie shot back with a laugh.

Sasha stifled a laugh and slowly turned and walked back to the bar.

We got back to chatting and she was filling me in on the now averted family crisis and that she'd be heading back in a day or two. She could see the relief in my face.

"Aww. What's the matter, baby? Your nice hard cock ripping through your pants in frustration?" she laughingly asked.

"Well, if you must know, yes," I responded. "I haven't cum since the other night you finished me off on the phone," I said then I paused. "Well now, that's not exactly true," I continued, "Billy texted me after I hung up with you and sent me a video that got me all heated," I ended by subconsciously licking my lips and smiling.

"Oh shit! Send it to me--I wanna see it!" she ordered.

I worked my phone and sent it to her. She watched it on her tablet and I could hear the sound of Billy jacking off. I could see her eyes bulge--just like mine did. I could see her lips moving, but I couldn't hear. I turned up the volume a bit.

Turns out there was a glitch in the signal and she (now) loudly said, "Oh fuck, this is making me so wet!"

My cock leapt to life just hearing her getting aroused. I quickly turned the volume down back to where it was.

Out of the corner of my eye I spotted Sasha now staring right at me. I could only see one hand on the bar and I started to think about what the other one might be doing. She must have heard Annie's dirty talk. I went back to Annie and she was still enjoying the video. As it finished, I could tell that she was touching herself in some way. I heard a glass set down on the table and I could now see Sasha was delivering a glass of water.

I thanked her and Annie shouted out, "Hey Sasha, let me ask you something." I started to hand the phone over and Annie stopped me by saying, "No, baby, I want you to hear this too."

I held the phone out as Sasha slipped into the booth beside me, so we were both on camera. I noticed her perfume as she got closer and it was nice. I couldn't help but see down her dress to notice her ample, perky tits pushed up high.

"I need a favor from you, Sash," she started. "My man here has a problem. I've been gone too long and he has a nice hard cock that needs attention right now. Could you help us out?" Annie fake pouted.

A jolt of fear shot through me but, instead of killing my arousal it intensified it.

Sasha looked away from the screen to look at me biting her bottom lip and then a coy smile formed.

"Is this true?" she asked suddenly and sternly like a detective from a crime drama.

I went with it. "What do you think?" I asked equally sternly, locking on her eyes.

Her eyes softened and a look of hunger washed across her face. Her hand was now on my thigh and moving slowly, but with purpose, towards my crotch.

She softly cupped my bulge and said, "Oh god Annie, I see what you mean."

"What do you think is the best way to help him, Sash?" Annie puzzled.

"Hmm, well I think it's best to start with a nice, thorough blow job," Sasha purred, her eyes laser focused on mine.

My breathing quickened as I started to worry about getting blown in a public place. There aren't any people around, but what about the back rooms of the place? My concerns quickly turned to static in my brain as her hand kept rubbing my dick through my pants.

She smiled as she moved under the table and I followed her with the phone's back camera. My belt was undone and my pants opened. All I could see now was the phone's screen with a dark image of my hardening dick being exposed to the air with Annie's face focused on every second in a small frame in the corner. I turned on the cam's light and there was her beautiful red lipstick covered, bee-stung lips making first contact with the head of my cock. Annie moaned. I could feel Sasha moan as I went deeper into her mouth.

Annie did her usual dirty talk coaching--this time to Sasha. Telling her to make me cum as fast as she can. Her mouth felt so good. All I could see from above the table was on the screen where her lips working my unit. Her cupping my balls and gently massaging them made me get hotter by the second. I could see her lips pushing all the way down.

I started to shudder and exclaimed that I was gonna cum. Annie's brilliant cheering pushed me over the edge. Sasha's lips slammed down on the base and my body tightened as I started unloading in her throat. With my free hand I held the back of her head as I thrust the rest of my cum into her. I felt her back off and kiss the tip of my dick as she got up from under the table. She slid back into the booth up against me and latched onto me slamming her mouth on mine. In a second, her tongue was finding my tongue and her mouth was full of my sauce.

I lapped it up and we continued to tongue each other until we were startled by Annie asking, "Hey, what the fuck?!"

We separated and both looked at Annie to see her laughing.

"Mmm. Tasty," Sasha hummed.

Without looking, she reached for the water and she brought to her lips and took a big sip.

Annie proclaimed, "Yeah, I thought as much, Sash. Why don't you take him in the back and let him fuck you? Baby, I don't mind you having a pussy proxy until I get back. Sash, I will tell you that he likes having his ass played with, so maybe YOU can fuck HIM too, hmm?"

Sasha looked to me with a raised eyebrow and asked, "You up for a little fun?"

I smiled and nodded yes and kept our eyes on each other as we started to get up from the booth.

Annie urgently spoke up, "Wait. There's one condition. I can't stay on the phone much longer--it's about to die. So you're gonna have to record it for me, so I can see everything. Deal?"

We both responded, almost in unison with, "Deal!" We said our goodbyes and I ended the call. I looked at her with a "what now?" shrug.

She took my hand and we went through a door by the bar. We entered a narrow hallway with red velvet paisley wallpaper lit by dim lights. There were two doors with one down a short side hallway labeled as a restroom. She opened a door at the end of the longer hallway and we entered a dark room. It looked like a good-sized studio apartment and I could make out a small office set up on one side in the darkness. There was a large four post bed in the back of the room. She dimmed the lights up slightly and walked me over to the bed. I dutifully set up my phone to record on the nightstand table and climbed up on the bed.

As she started undressing me, my hands worked down her shoulders to her breasts. I squeezed lightly and I could see her nipples were hard through the fabric. She had me down to my boxers and told me to lie on the bed face down with my ass in the air. I was shaking with excitement when she told me to do this--and I obeyed.

She kicked off her high heels, her dress slid to the floor and I could feel her now naked breasts sliding over my ass. She stuck her fingers in the elastic of my boxers and slowly pulled them over my ass cheeks, and I let out a low sigh. She got them the rest of the way off, and there she was--her skin on my skin. She moved her hands over my back as wonderful breasts slid up the back of my legs and over the top of my ass. My cock had recovered and was starting to pulse from my increasing blood pressure.

I felt her hands spread my ass apart and then her hot breath in my crack and heating my pucker. Then I felt it--her tongue touched my rosebud and I tightened up from the surprise and the pleasure.

"You ok?" she asked.

I replied almost moaning, "Ohh, I am sooo good."

She giggled. I felt her again against my back door. This time she went all in--with her tongue. I gasped and moaned a split second later. She gripped my ass cheeks and spread them apart as she pushed her tongue in deeper. Her hand found my cock and she started milking me.

I started shaking all over as she played me like a musician plays an instrument. I started fucking her tongue and she moaned as I pushed harder.

She sighed and moved away and asked, "I think we're ready for a little strap-on action, don't you?"

I moaned yes into the pillow. I could hear something being assembled with buckles clanking, and she jumped off the bed to get something. She was back in a flash and I could feel the familiar touch of a probing finger covered in lube. She started working in one finger, then two, then three.

She started to go for four and I protest moaned from inside the pillow.

"Ok, maybe you'll change your mind a bit later," she said cheerfully.

She asked me if I was ready and I said yeah. Her hands were back on my ass cheeks and slid slowly to my hips as she started to close the gap between us. I could feel something at my back door, and slowly it started its way inside me. It didn't feel very big--compared to Billy, anyway--but it was feeling really good. She asked how I was doing and if anything hurt--I said on the contrary--it felt amazing.

Soon she was all the way inside me and started to pull out. Then back in. Out. In. Slowly, lovingly. She reached down and pressed her firm breasts into my back, and she kissed her way to my neck. I moaned. She whispered in my ear that if I was game, she had something bigger that would feel even better. Just a bit worried, I paused and asked how big. She replied that it's about 10-11 inches and kinda thick. Billy's cock flashed into my mind suddenly, and I wanted it.

I cocked my head back to make sure she heard me and I said eagerly, "Let's try it."

She said she needed more lube and jumped off the bed. I could hear buckles being adjusted and things being moved, and she was back.

"Are you ready for me, baby?" Sasha asked in a sexy whisper.

I moaned into the pillow. Then I felt it...the head was straining against my sphincter, she backed out, and then pushed back again. I was told to breathe deeply and relax--I did. On my last breath out, she pushed, and the head slid in. I gasp-moaned into the pillow and I moved forward a little as it stung a bit. I raised my hand up to say wait. I tried to relax my ass as much as I could. I was wishing I had some poppers about now. When I was used to it, I started pushing back against her and she slid in more easily past my sphincter. I gasped loudly into the pillow.

"There ya go, that's it! Do you like it?" she asked with a sultry tone to her voice.

I shook my head yes quickly into the pillow as I gripped the bed covering tightly.

"Here we go, baby," Sasha warned.

She started pulling out slowly and back in with short strokes, and I started meeting her thrusts by pushing back on to her. She was speeding up her thrusts now, and I was in heaven.

She slowed down suddenly, almost to a stop, and said, "I want you to roll over for me."

She pulled out with a wet suction pop and I rolled over. She was on top of me quickly, sliding her tits up my stomach as she flicked my nipple with her tongue and a little suction. There we were face to face and she passionately kissed me--and I kissed her back. I could feel her maneuvering her body, and I could feel her strap-on searching for my opening. She found it quickly and started pushing. The head popped in more easily this time, and soon she had it deep inside me.

We kissed again through moans, and she picked up her thrusting. I wrapped my arms around her and pulled her tight, feeling her breasts rubbing against my nipples. I moaned again and she moaned with me.

"Do you like how I feel inside you, baby?" she asked.

"You feel amazing. I feel so full," I answered back.

My hands worked their way down to her ass and squeezed. She started picking up the pace now. Her stomach was rubbing against my hard prick, and it was now wet from the juices dribbling out of me. We started matching our rhythm perfectly. We were one.

"I'm close to cumming, are you?" she asked breathlessly. I moaned and grunted a kind of a yes!

"Where do you want it, baby?" she asked. Puzzled, all I could come up with was HUH?

"Do you want me to cum inside you?" she asked breathlessly, straining at having to ask again.

Then it all clicked in a flash of realization...I didn't see her without panties on...my face was in the pillow most of the time--and I'm now realizing as my hands are moving on her ass that wasn't wearing a strap on.

"Let me fill you up with my cum, baby. Annie said it would make you cum real hard," Sasha panted.

This was all because of Annie. She wants me to get fucked by a hot, beautiful tranny with a big cock and see it on video. I glanced back at the phone and there it all was--perfectly framed and still recording.

My body was starting to get that tingly feeling like when I took poppers. I was on the verge of cumming with a huge cock thrusting up my ass and that cock is going to fill me up with HER cum. I couldn't resist her and what I was feeling. I quickly surrendered.

"YES! Yes! Cum in me! Fuck me hard and give me your cum!!" I grunted.

Sasha sped up her thrusts and started hammering me hard. I looked down between us to see her big hard cock disappearing inside me. Then there was that feeling...my entire body was tingling, and my legs started tensing up and I pulled my knees up past my hips. A long moan escaped me as I saw my cock spurting cum everywhere as it moved. Sasha moaned loud and wrapped her hands under my shoulder blades and pulled herself even deeper inside me. I could feel her cumming--pulse after pulse after pulse. Feeling that inside me made me quiver and buck. I grabbed her ass and pulled her hard against me, forcing that dick as far inside me as I could get it.

We finally slowed and stopped and she stayed inside me. She smiled at me and kissed me lightly on the cheek.

"You mad?" she asked sheepishly with a raised eyebrow--almost like she was expecting an attack.

"For a split second I was, but not at you--at Annie. But then I know she wants me to be happy...and wow am I happy," I said as I started laughing.

Sasha joined in too and kissed me again. "Damn, that was so hot!" she said as she backed off me and slowly pulled out of me.

She looked down and said, "Look at me, with your cum all over my belly."