Ann: a Love Story
Bdsm Story

Ann: a Love Story

by Mimaster 18 min read 4.8 (45,000 views)
role playing anal sex first time anal ass to mouth light bdsm tied
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© 2025, All rights reserved -- mimaster

~ * ~ * ~ * ~ * ~ * ~ * ~

Dawn and Jill had departed to separate ends of Mark's tasteful home. Jill and Mark's room was to the right as you entered. Dawn's, and a room Mark used as an office, were down another hall to the left. The living room was in the center of the home, with the kitchen behind it, combined as kind of a great room complete with a cathedral ceiling. As double wide mobile homes go, it was very, very nice. It actually felt like more of a house the way it was set up.

The floor plan allowed Dawn to have some semblance of privacy. But as loud as we had been the night before, the illusion of being secluded was pretty much shattered. Still, it was neat that Mark and Jill were able to give Dawn her own space, complete with a separate bathroom on her end of the home.

Mark and I were sitting in silence, mentally recovering from the visual overload the girls had just subjected us to. I, for one, was glad. Any contact between Dawn and I right after the live and taped lesbian show would have had me cumming in seconds. As it was, I was able to get control of my libido enough that I was confident I would be able to control my ejaculation. I wasn't so sure about Mark.

I was finally able to see, my eyes adjusting to the dark. He was panting, looking like a tiger hidden in the jungle, waiting to pounce on the first piece of fresh meat to mistakenly cross his path. He was going to have a hard time controlling his carnal instincts. My first thought was that Jill was going to be disappointed, because she had Mark so worked up, it likely was going to lead to a very quick

fuck and done

encounter. And that would be a shame considering the time, effort, and sexual energy she and Dawn had put into their erotic performance.

That thought got slammed up against the inside of my skull, pummeled by a new one that was fighting to the death for control of the preeminent position at the front of my brain. The cause of that new thought was standing to my left as I sat on the loveseat.

Jill was looming at the edge of the same hallway where she had walked onto the 'beach', which her living room had represented in what appeared to be the previous scene in the adult movie we'd been watching. She was illuminated by the candlelight from her bedroom. From the amount of light, there seemed to be much more lit than just the couple of dozen that had set the mood for my brief tryst with her. And that suddenly seemed like days ago instead of a little over an hour.

She was wearing a black leather bikini and long black leather high-heeled boots that came up past her knees. I normally would have been leering at that, considering how amazing it made her body look.

However, I couldn't get past the wig. She was standing, legs apart; a dominating sneer appeared on her face. This girl was an actress, and sge was channeling her character before she even took to the stage. Atop her head, she wore a shoulder length red-haired wig. My mouth dropped as she strutted past me, ignoring me on the way by. She stood tall in front of a frozen Mark, lifting his chin with her fingers to get him to look into her eyes.

"Stand up, Anthony. Sophie wants to play."

MY

heart jumped. I could only imagine what Mark's heart was doing. Jill was going to the next scene. She'd mentally rewound the tape, going back to one we'd already seen.

He stood up slowly, and Jill turned him around. He didn't flinch when she took a tie and bound his wrists behind his back. Smacking him on his ass first to get his attention, she took him by the elbow.

"Let's go Anthony. I've waited for this long enough!"

They disappeared behind their door, leaving me alone with my thoughts in the dark. Scattered, random things popped into my head. It had been a whirlwind weekend to that point, and I was waiting on another overwhelming encounter with Dawn.

As much as I had enjoyed Jill, I couldn't wait to be back in Dawn's arms. Unless, of course, it wasn't Dawn that was behind that closed bedroom door any longer. As intrigued as I was, I prayed a red-haired girl in black leather didn't come sauntering out for me as well.

~ * ~ * ~ * ~ * ~ * ~ * ~

No matter how long eternity is, when it comes to waiting for a woman to get herself ready for a man, add twenty to thirty minutes. Not that I minded. I knew it was time well spent on her behalf, and it would be worth whatever wait I had to endure.

Dawn's door opened slowly. The candlelight coming down the hallway showed her shadow seductively turning down the sheets to her bed. I had that same shiver of excitement hit me just as the night before. How something so domestic could be so sensual was beyond me, but I immediately got excited. Not just because she was inviting me to her bed again, but because, just like Jill with me, she hadn't invited Mark.

I looked at Dawn's shadow, checking out just how much attention to detail she'd put into whatever she had been planning. She had carefully positioned the candles to project a perfect silhouette on the opposite wall in the living room. I wondered how long it took her to figure out the proper placement to get the effect she was looking for. It didn't matter, because in doing so, she had deliberately created a new medium for me to view.

She lifted her hand, and crooked her finger, beckoning me to come to her. She knew I'd be watching, and waiting. When I got to the doorway, she was on the bed; legs curled under her provocatively to show her nude form from the front, but not being vulgar about it. Her upper body supported on her right side by her elbow, her right hand holding her tilted head. Her left hand was twirling her platinum blonde locks.

I leaned into the doorframe, crossing my legs at the ankles in a patient pose; other than my hard cock pointing almost directly at her. Quietly, I said, "Hello Amanda."

She fought to contain the squeal that emitted from her chest. I'd let her know that I knew what she wanted, and I was willing to play along. Her eyes lit up as big as her smile. The more times I showed I really got what made her tick, the more excited she became.

She patted the bed with her left hand, saying, "Hello Dean. Why don't you come join me? I've waited a long time for this!"

Seeing her in a blonde wig gave her an entirely different persona. Not just because she was playing a part she fantasized about from a porn movie. Her aura was altered. While I loved the real, brunette version, this different model was equally exciting, but in a different way; one that I couldn't put my finger on. I know one of the things that helped her pull off the stunning transformation was that she was clean shaven below, so there was no evidence that she wasn't a natural blonde. But the sexual aura she was sending off was a totally different vibe from my Dawn. She was Amanda.

I started to close the door behind me as I walked into the bedroom.

"Leave it open Dean. Maybe we'll hear Sophie take care of Anthony while you take care of me!"

It was definitely out of character from the movie. Dawn was putting her own personal spin on the scene. An erotic rewrite of sorts. I played along, pushing the door back to the original position before I turned and walked to the open side of the bed. If she wanted to direct her own happy ending, who was I to argue? But I couldn't help but smile when I thought of the overwhelming theme of the scene between Dean and Amanda. No matter how you edited or changed the direction, it all came down to two words: anal sex.

Because she was in the middle of a rewrite, I decided to test the plot to see where things were going. "Do you really think we'll be able to hear them?"

She winked and said, "We will if Sophie leaves her door open like I asked her too. Anthony won't be able to do it. He's probably already tied up by now."

I slipped in next to her body, moving behind her as she faced away from me. My cock nestled perfectly into the crack of her ass as we spooned together; a foreshadow not lost on her.

"God, Dean, your cock is already so hard. It feels so hot against my ass."

I cupped her breasts, pulling her tight against my body as I squeezed them; kneading the soft flesh in my big hands. I was rough as first, trying to get a sense of her sexual temperature. Did she want a suave and gentle Dean; or was she more interested in the rugged and dirty version?

"Oh God, that's it, baby. Maul my tits!"

"She wanted it to be rugged and dirty. I was ready for that. I had made love to Dawn many times already. That's what our being lovers was all about. But in the bawdy X-rated play in which I was about to make my thespian debut, the role I was cast in called for stepping out of that safe zone, and portraying a character more diverse. Dawn loved being loved; Amanda wanted fucked. I'm sure that Dawn had times where she wanted fucked too, but I wasn't with her at the moment. I was with Amanda, and that thrilled me.

I pawed harder at her big breasts, pulling and squeezing her nipples as I humped my cock in the crevice of her backside.

"That feel's so bad, baby. It makes me feel so dirty!"

"Are you a bad girl, Amanda?"

"I want to be. Make me be a bad girl, Dean. Make me be naughty!"

At first, I wasn't sure how I was supposed to

make

her be naughty. I figured she was already there. But I knew where she wanted to end up with that scene. Maybe she needed to be sort of forced to do something so out of the norm. I wasn't sure, but my gut told me that with her using words like 'make' and 'dirty' and 'maul', she wanted me to be more in control than to have this be a romp where we were on equal footing.

I grabbed her and flipped her over onto her knees while I got on my back. I thought about grabbing her hair and kind of getting her where I wanted her to be, but I didn't want to pull the wig off by accident. Instead, I pushed her down by her shoulders and kind of growled at her.

"Suck my cock, Amanda. Suck it now!"

It was a demand rather than a request. She squeaked a little as she felt my strong hands move her down my body. Grabbing my shaft, she took me gently into her mouth. Gentle wasn't going to do for Dean either.

"Suck it! Don't play with it!"

I grabbed the back of her head carefully so I wouldn't disturb the wig, but I pushed her head down forcefully onto my shaft, making her gag a little. I started humping my hips up, forcing more and more of my cock into her mouth. Dawn let out her own little growl as she tried to stuff more and more past her lips.

When she was gasping and pulled up to take a breath, I swiftly changed positions and threw her on the bed on her back. Taking her legs and flipping them up over my shoulders, I buried my slobbery cock deep into her pussy in one violent thrust. She screamed out as I started pounding her. There was no doubt in my mind that Mark and Jill... and Anthony and Sophie for that matter, heard that.

I pumped into her hard, pinning her knees near her head. She was grunting with every thrust. I kept in mind the end game, wanting to make sure I was in control of my orgasm so I didn't screw up Dawn's fantasy. I knew her ass would be tight, and having not experienced anal before, I was a little nervous I'd shoot off to soon. I needed a way to transition to her ass. I needed a compelling reason for Dean to

make

Amanda do it. She gave it to me a few minutes later with her pleading.

"Oh shit, Dean! Fuck my pussy. Fuck my pussy like I'm a dirty slut!"

Snapping totally into character, I shot her a nasty little grin.

"Dirty sluts don't want their pussies fucked, Amanda. They want their asses fucked!'

"Oh shit. Yes! Fuck my ass! Fuck me in the ass, Dean!"

First, I shoved a finger deep into her ass, and I smiled as it slipped easily in. She'd had the good sense to take the time to prepare her rear entrance with a water-based lubricant of some kind. I made an educated guess that she also gave herself an enema to clean herself out, considering the smutty ending her selected scene chose. That would explain the time it took for her to prepare herself after she and Jill had left the living room. But that was just a guess. I didn't really know at the time.

Finger fucking her ass for a moment, I slipped a second finger inside her tight hole, and then a third, all the while still fucking her glorious pussy. I got a glimpse of Dawn's sexual desires. The look on her face from having both of her holes stuffed, even with my fingers, said volumes. She loved it. It was time to see just how much she enjoyed having her ass full. Three fingers was just an appetizer.

I pulled my fingers from her ass, and my cock from her pussy.

"Spread your cheeks, Amanda. Show me how much you want my cock in your ass!"

Dawn moved her hands quickly; faster than I thought Amanda would have. Nonetheless, the split personality underneath me pulled those tight buns apart, offering her virgin hole for me. That, too, was a guess, but I felt a little surer on that one. I placed the tip of my cock against her rectum and slowly eased forward. As my fat head popped past her sphincter, her eyes almost popped out of her head.

She started sweating, and she was breathing erratically.

"Calm down Amanda. I don't want you to pass out. Relax. I'll take it slow... at first!"

She was panting as I gave her another inch, and then another. Halfway in, I pulled out and slowly gave it back to her.

"FUCK!" she said as I gave her a quick jab.

She was gritting and grinding her teeth, breathing through them like a mad dog. The drool was running out the sides of her mouth. It all seemed so primal.

"MORE. GIVE ME MORE, DEAN!"

I obliged, shoving another inch of my wide shaft into her anal cavity. She screamed out again, and pulled wider on her ass cheeks. I grabbed her ankles and spread her legs wider, giving me even more room. The fact that she was so well lubed helped me slide into her, but she was struggling with the girth of my flesh. I wasn't sure if she'd practiced with anything before, but if she had, it wasn't as wide as I was.

After ten minutes, I was finally buried all the way in Dawn's ass. Her eyes were glassy and shaking quickly back and forth... like REM sleep with her eyes open. I let her get used to the fullness and length for a moment. The last thing I wanted to do was hurt her.

"All right, my dirty little slut. Are you ready to fuck?"

"Oh fuck yes, Dean. Fuck my ass! Fucking fuck my fucking ass, you ass fucker!" It was an interesting phrase, one I was sure my high school English teacher had never tried to dissect. I don't think my college professor could have solved it either. But it certainly made her point.

I pulled all the way out, and slowly pushed all the way back in. I continued, picking up the pace as I went. After a few minutes, I was hammering away at her back hole as hard as I had ever fucked a pussy. The tightness of her hole made my legs weak in the position I was in. With her bent over like she was, the angle of her body forced me to be slightly off my center, and I had to make up for lost leverage with sheer power. It was taking its toll.

I pulled out, and was surprised to see her asshole stay gaped open.

"OH SHIT... OH SHIT, DON'T STOP. DEAN! PUT YOUR COCK BACK IN MY ASS!"

"Get on your knees, Amanda! I want you from behind!"

Dawn flipped over onto her hands and knees, wiggling her ass a little, as if I needed any additional inspiration.

Grabbing her by the hips, I pulled her onto my shaft as I shoved my hips forward. I immediately felt the difference in leverage, and started pounding her. My big balls slapped up under her body, making wet smacking sounds as they hit against her pussy. Reaching below, I started playing with her clit, and she reacted in an instant.

"I'M CUMMING DEAN!" she screamed at the top of her lungs. Again, I knew our roommates on the other side of the house heard that. Maybe even the neighbors down the block.

I quickened my pace, and stroked her deep until she collapsed forward onto her chest. The orgasm ripped through her, the sweat running down from her lower back toward her shoulder blades. My balls started to ache, and I knew I wouldn't last much longer. The angle of her torso put more friction on the base of my cock, and made each move forward a new sensation in pleasure.

She pushed herself up onto her forearms, which relieved some pressure on my straining shaft. I thanked her by clawing her tits, abusing her protruding nubs. She reacted in kind, humping back into my groin as hard as she could.

"Come on baby! Give me your cum! GIVE ME YOUR FUCKING CUM!"

The way she'd demanded my load felt more like Dawn was wanting it than Amanda. It didn't matter, I was happy to oblige either of them. The moment of truth arrived. My balls started to contract, and I knew I was seconds away. Dawn knew it too. I wasn't sure what Amanda knew. The only question I had at that moment was; what would this wonderful woman I was fucking in the ass do, now that I was about to bring the fantasy to a close. Would Dawn just have me cum in her ass, or would she remain Amanda to the end.

"I'M CUMMING AMANDA!" I shouted, giving her fair warning and wanting anyone within earshot to know.

In my mind, I knew the end of that movie scene. It was the one I had etched indelibly in my head, other than the beach scene. Fairly convinced that Dawn had never had anal before, it was hard to imagine she'd rehearsed this one like she had the beach encounter with Jill. But she'd definitely remembered the script. Acting just like Amanda, she pulled off, and flipped her body around in what would have been perfect unison to the tape. I did the same, quickly standing. Her platinum hair floated in the air as she grabbed my cock and massaged my balls.

I wanted my own fantasy now.

"Suck my cock, Amanda. Suck it like the naughty, slutty girl you want to be!"

She looked up into my eyes and took my cock deep into her mouth. Moaning around it, she took as much in as she could. Then she changed my ending, and I must say, for the better. Amanda became Dawn, as she pulled off the wig to reveal her long brunette tresses. I grabbed her head and held it, running my fingers through her hair as I started bursting.

"Fuck, Dawn... that is SO HOT!" I screamed as I filled her mouth.

Just like the movie, she let my load flow past her lips and run down her chin to her chest. I was so worked up I was able to shoot my normal load, much to her delight. Spent, I finally fell back onto the mattress. Dawn jumped on top of me and started kissing me, rubbing my cum between us, making me taste my seed. She knew I didn't care, and that turned her on more.

Behind us, I heard clapping in the doorway. Looking back over my head, Jill stood there, still in her red wig and her leather outfit.

"That was so fucking hot, Dawn. Thank you so much for letting me watch!" It certainly became clear why Dawn wanted me to leave the door open. I don't know how long she had been standing there, but it was obviously a very long time. I was stunned, and was about to say something, but I didn't have time. We apparently had somewhere we had to be... right away.

"Our turn!" Dawn said, grabbing my hand.

I was having trouble walking, but she helped me by pulling at my dick to lead me.

"We're not going to watch for long," she whispered to Jill.

Jill nodded, knowing it was late, and we needed some sleep. She had left her own door open so Mark could hear us. He couldn't see what we were doing because he was tied up, spread eagle on their bed, and also because Sophie had blindfolded him. Dawn and I stopped at the doorway, not wanting to enter the sanctity of their room. It seemed a little silly, and yet it was entirely the right thing to do. After all, Jill had done the same. We were invited to watch; nothing more.

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