DISCOVER

Dated a girl that I would often call beautiful. One day she told me to stop. So I did. It was part of what broke the relationship. I thought she was beautiful she didn't.

Very hot

Weekend with the Boss

I’d just started at this new job a few months ago and my boss Lisa was so nice to me, we’d been play flirting for a while, she was really hot, a Megan Fox lookalike. Huge tits, great ass and legs to die for. I knew I couldn’t get with her because she was the boss but the flirting was getting a bit intense, until one day in her office we were joking about my ass. My ass was good, firm, peachy, I’d been working on it at the gym on leg day, and then my boss said ‘oh I’d love to peg that’ erm what.

This stayed in my mind for the rest of the week, the thought of my boss pegging me, surprisingly, it turned me on quite a lot. We had a works do at the weekend and I was looking forward to flirting with Lisa again, we were both single so it was fine in theory, I just didn’t know whether getting with the boss was a big no no or not.

I dressed up for the works party, my sexiest boxers, tight chequered grey trousers and a dark blue shirt that was probably too small but made my muscles look bigger than they were, 3 buttons undone because it wouldn’t button up all the way anymore. I got there and got a few drinks in, the workforce was mostly girls and so I was the centre of attention, being cheeky with them all and making them laugh.

‘You look great!’ Lisa said as she came over in a light blue satin dress that hugged her curves perfectly, ‘wow so do you Lisa!’. We flirted for a while and got drunker and drunker. Eventually she asked me to walk her home, when we got to hers she invited me in for a few drinks, I was way past caring whether this was appropriate with the boss.

As soon as Lisa shut the door behind her she kissed me, our bodies came together as we made out and moved towards the couch where she lay on top of me. Lisa got up and pulled my shirt off and my trousers down, I was obviously very hard already. Lisa smirked and beckoned me to her bedroom, she lit some candles so there was barely any lighting as I got on the bed.

Lisa straddled my chest in her sexy dress, this was it, I was going to eat her out so hard. ‘Your cocks nice, but I hope you’ve got an open mind’ Lisa told me, my cock was about 6 inches so I was happy with this comment. My cock sprang to attention as she pulled up her dress and where there should have been some panties, was a huge cock. Lisa was a shemale? I was so confused, she carried on pulling her dress off and then pushed her cock towards my face. ‘But it’s not a real cock like mine’ I was so turned on but in bewilderment at the same time, I didn’t know what to do, I wanted to get up, I wanted to - I wanted.. I wanted to suck her cock.

I opened my mouth as Lisa thrust her cock into my mouth, it tasted better than expected, I couldn’t fit all of it in but I moved my tongue around like the girls I’d shagged in the office did to mine, Lisa moaned to let me know I was doing a good job. Her cock grew and grew and grew, growing to about 9 inches, I knew what she meant, it was magnificent, my cock was nothing compared to this. Her cock was pulsing as she climbed off my chest, ‘take those boxers off and get on your hands and knees’

I did as I was told, loving how bossy she was, she poured lube into my ass and onto her cock, she put just the tip in ‘I’m just going to let your ass adjust to this size’ so far so good it felt great. She pulled it out to inspect and I moaned, Lisa giggled as she said ‘oh you already miss it, this is going to be fun’ she re-entered my ass, and then rammed her cock in balls deep. Lisa fucked me hard, my ass was in ecstasy, loving every inch of her cock, she carried on fucking me as hard as she could, her balls hitting my gooch and sending waves of pleasure up my dick, I was rock hard, my cock swinging with the motions,

I felt Lisa’s cock pulse and throb as she came in my ass, flooding it with cum. But she didn’t stop, she kept fucking me until we changed positions, me on my back watching her tits bounce as she fucked me, the night carried on like this until we fell asleep.

I woke up. I was the little spoon and Lisa’s cock was rock hard against my ass, now it was light it looked even bigger, monstrously huge. Her morning wood put mine to shame. I got up to go for a wee, climbing out of the pink silk bedsheets, her room looked amazing.

~clink~

I looked down. My glasses weren’t on but I could see something metal on my cock, I grabbed my glasses and saw a cage on my cock, with a lock on it. Lisa must have locked me in chastity last night, I frantically looked around for a key. Nowhere to be found. I went to the toilet, sitting down to pee. I came out of the bathroom and found Lisa stroking her cock. ‘Morning Bitch, what do you think of the cage?’ ‘I don’t remember this being put on last night’ ‘Well I thought since your cock is nowhere near as big as mine that I’d lock it up, we won’t be using it anytime soon’ ‘But what if I want to masturbate?’ ‘Well that won’t be happening, you can come to my office and get fucked by me’ my cock was straining in its cage, this sounded hot but very sudden, I was completely fucked, she owned me now and she knew it. ‘Get back in bed with me, it’s Saturday and neither of us have anywhere to be’ I got back in bed and she spooned me again, she reached around and fondled my cage, stroking it, squeezing my balls, rubbing the head, I was so aroused, she knew exactly what she was doing.

Then she started to put her cock in my ass, I arched back so she could put it in, I may as well learn to love this. She started to fuck me again, my cock bulging now, throbbing with frustration as I got more and more turned on. Her tits pressed against my back, her cock thrusting in and out of me, her hair tickling my back and neck as she nibbled my ear lobe ‘I have the keys to your cock, I own you now, you’re going to move in with me, then I can fuck you all the time’. After she came in my ass again, she told me to put on her lingerie, a black thong and bralette, as my boxers were nowhere to be found, put on my shirt and trousers and sent me home to get my stuff.

For the rest of the day I packed all my belongings, paid off my bills, sorted everything with my landlord and came back to Lisa’s, she unpacked all of my clothes and then gave me a box of all my underwear. ‘You’re going to throw all of these out and we’re going to go shopping for some lingerie, you need to dress like the slut you are’ my cock throbbed in response, rubbing against my thong and trying to get harder. Lisa grabbed my cage through my trousers and said ‘I’ve been looking forward to this ever since you started working for me, last night was amazing and that was only the beginning’ she pulled me closer and I felt her huge cock against me as she kissed me. This was going to be amazing.

Maid

It is my first time in a gym in many years.  I meander around, kinda lost.  A well muscled man that looks to be mid thirties approaches me with a smile.  He is shirtless and in blue gym shorts that show an impressive bulge.  "You look a little lost. Would you like some help, and a workout partner?"

I smile back and say quiet and timidly "Yes, I could definitely use some help."

He chuckles and says "I thought so.  Let's do some squats to start.  You get ready, I'll load it for you."

I get squatted in the machine and he walks back in front of me.  His crotch is inches from my face. I subconsciously lick my lips. "I'm ready to spot for you, get going."

I rise up, my eyes roaming his body as I do.  Higher and higher until we are face to face.  I blush because I'm sure he noticed my looking. I go back down slowly until I'm looking at his crotch again. It seems like his bulge has grown. 

We continue this routine at different machines. I always seem to wind up with his crotch in my face every time.  I'm pretty sure that he is getting harder as we go.

At the bench press he stands over my head and I can see his cock hanging loose in his shorts.  I lick my lips again and hear him chuckle as he sets my weights.  He adjusts himself when he steps back and my eyes stay locked on his cock.  I do my workout trying not to stare at his crotch.

I finish and he slaps my inner thigh as the weights settle. His hand does a little rub and he says "That'll do for today.  You've had a decent work out.  You're pretty tight right now.  Let's hit the shower."  When he said tight he squeezed my thigh and a small moan escaped my throat.  

We head for the locker room. "Get this locker.  It's beside mine. Get ready and I'll show you where the showers are."

I'm very nervous now because I'm wearing a pink satin thong.  I hadn't planned on stripping next to anyone.  I had just spent the last hour looking at his crotch and licking my lips and now he was going to see my panties. 

He looks around and we are mostly alone. Two other guys are chatting on another bench, but aren't paying any attention to us.  He leans close, his lips by my ear.  His hand reaches out and caresses my ass cheek.  I feel his hot breath in my ear. "I saw the thong before I talked to you.  You bent over and flashed it like a slut.  Then you acted so shy every time you looked at my cock. Are you a Sissy Slut?" 

His fingers slip into my shorts and find my asshole. He slips his fingertip in and I moan.  "Yes, but I'm new to this.  I need to be trained in this too."

He grunts and his finger goes in more. "I'll train you, slut.  I'll make you my Sissy gym slut. I'll feed you my cum after every workout." 

He steps back and drops his shorts.  I'm amazed at his size. His cock is over nine inches and he isn't hard yet.  I lick my lips and my hand automatically reaches for him. He pushes my hand away and whispers "Not now, slut.  You can look but don't touch until I tell you to."  He wraps a towel around his waist. "Hurry up" he commands. 

I quickly strip, hiding my panties inside my shorts, and wrap up in a towel.  We walk to the showers talking about our workout.

We go to the corner area of the showers to be able to see anyone coming in and hang our towels.  I can't help but to stare at his cock and think about what he will do to me with it.  I become fully hard.  I stand under the water let it pour across my body.  He begins to stroke himself since we are alone.

"Spin around and bend over, slut.  Show me your ass."  I turn around, bend over and spread my ass letting the water splash me. "Nice. You are a slut.  You want it so bad.  Sorry, but we have to be good here, or I would fuck you right now."  He stops stroking himself and spanks my ass one time.  "Hurry up, slut."

We quickly shower and head back to our lockers. I get into my gym bag for clean clothes and quickly slip clean pink panties on. He smiles and I pull my shorts over them as fast as I can. I sit on the bench and I'm looking right at his cock when he takes his towel off.  He talks to the guys on another bench as it swings right in front of my lips.  He takes his time talking and not putting on his shorts. He puts on a tank top first, then he turns his ass to my face as he starts to put his shorts on. He turns back to me as he pulls them all the way up.  I lick my lips again.

He looks down at me "C'mon, bud.  We need to hit it." I finish up quickly and we walk outside. I follow him to his car.

He opens his door and pushes into me by the open door. I can feel his cock rubbing against me.  I reach down for it.

I slip my hand into his shorts at wrap it around his cock. I begin to stroke him. He pushes me down into the seat and pulls his shorts down. His cock is fully hard and right in my face.  I lick the tip and suck on his head.

"That's it. Suck Daddy's cock, slut." I go down him. Taking all of his cock I can. He begins thrusting his hips and fucks my face.  My tongue tries to swirl around his massive tool as he drives it deeper into my throat. "Suck it bitch.  Take my fucking cock slut." My dick is twitching in my panties as he uses my mouth to get off.  I feel his hot cum blasting deep in my throat. I swallow it all and pull his ass trying to get more of him in me. I start shooting cum into my panties when he says "Swallow Daddy's cum, Slut.  Show Daddy how much you love his cock."  I lick and suck every drop from him.  He pushes me away and pulls his shorts back up.  He looks down at the large wet spot on my khaki shorts. "Very good Sissy.  You really like Daddy's cock, sucking it made you cum.  Just imagine how much you'll cum when I fuck you with it." 

He pulls me up from his seat. I'm in a daze.  I had just sucked my first cock.  I had swallowed my first load of cum. I came from sucking cock, and when he talked about fucking me, my head spun. I wanted it bad.  I was ready to do anything he asked to have him let me have his cock in any way. 

He hands me a card and says "Same time tomorrow. We'll work out, then we're going to my place. You'll need some Sissy outfits if you want to be fucked. I'm straight and only fuck Sissies and girls.  I plan on training you to be my perfect gym slut."

I walk away. My truck is on the other side of the lot, so I cover my wet crotch with my bag and walk that way.  My mind going through all my outfits that I want to be fucked in, and on which heels.   

I hope she is.

Gorgeous

Sexy AF

Packed