by Drew Sera
When I was sure that Sydney would be able to stand if I let go of her, I unwrapped my arms from her body and stood to the side of her. She was flushed and needy.
“Sunshine, go stand by the bed and turn to face Colin and I.”
Anthony gave her instructions and then he pulled two chairs away from the wall so that they were about five feet from the foot of the bed. Sydney did as instructed as Anthony sat on the back of the chair and put his feet on the seat while I sat on the other chair in a normal fashion.
And there she stood, innocently beside the bed with white, puffy, down comforters and bedding, waiting for direction.
“Sunshine, remove your clothes. Slowly.”
Sydney slipped off her shoes and jeans, followed by her shirt, bra and then panties. She folded everything neatly and placed her clothes under a small table near the bed. She resumed her post next to the bed and looked over at us. No sign of fear or unease. I swelled with pride knowing how much she trusts us and how brave she was to get completely naked in Irons again.
“Good girl, sunshine. Now, walk over here and help Colin out of his shirt and then come take my shirt off.”
Sydney padded over to me and I stood to meet her. My hands found their way to her hips. I checked her eyes to make sure she was still doing fine as she unbuttoned my shirt and tugged it off my body. I loved the way her hands lingered for an extra moment on my chest and how she ran her finger down the center of my chest. I sat back down and watched her remove Anthony’s shirt and she spent the same amount of time with her hand on his chest too. Anthony sat down on the back of the chair and instructed Sydney to go kneel on the bed in the center. Once she climbed on the bed, she turned and checked her location and proximity to the edges to make sure she was as close to the center as possible.
Before Sydney, Anthony and I had done just about everything and anything with a sub or bottom. While I enjoyed those times, I realize now that my heart was never truly in it. Or at least it wasn’t near the degree that it is when I’m with Sydney. With Sydney everything was exciting again. Even something like just watching her disrobe was exciting. Things that had once been commonplace barely sparked a twitch in my pants yet I could get a full on erection just holding her hand. And I knew that Anthony was at the same juncture that I was. Before Sydney, Anthony had been more on autopilot than I was. Neither of us knew we were searching for something or missing something. And then we found everything in Sydney.
“Rub your hands over your breasts, sunshine.”
Anthony and I sat watching our girl rub her breasts, every now and then hiding a nipple from us. She was shy, but I think the dim lighting helped give her confidence. I knew that a playful, flirty, little fragile kitten was just below the surface. She just needed some encouragement and her soul needed some nourishment.
Sydney never took her eyes off us. She knew we often required her to maintain eye contact with us. It was one way that Anthony and I knew we could detect and head off any possible issues and triggers.
“Suck on your finger and then rub on your nipples…good girl, sunshine…give them a tug.”
A soft moan escaped her mouth as she tugged her left and then right nipple.
“Does that feel good, Sydney?” Anthony asked her in a low, quiet, calm tone.
“Yesss, Sir.”
“Suck on one of your fingers again and slowly take that hand down between your legs.” She sucked on her middle finger and let her hand skim down her chest and belly before slipping between those legs. “Push it into your pussy.” Her eyes fluttered and she started to close her eyes. “Eyes, sunshine. Colin and I need to see them.” She opened them and kept her attention on us. “How does it feel down there, sunshine?”
“Wet, Sir.”
Anthony and I laughed quietly and glanced at one another.
“Good, sunshine. Pinch your nipples while you rub your pussy. Pinch those nipples until you feel it between those sexy legs.”
She hung onto each of his words as if it was the air she was breathing. The sight of her kneeling up on a fluffy bed wearing a play collar, with her hand moving around between her legs nearly undid me. I knew Anthony was ready to burst as well.
She let out another moan that sounded like she was dripping with need. Sydney is so used to having to be quiet and has it burned into her head not to show signs of pleasure or make noise. Anthony and I were going to turn that around. I wanted her to enjoy it and be able to express herself.
Sydney continued to rub her pussy lips and pinch and tug on her nipples until I saw her stomach muscles tighten and her eyes get heavy. It made Anthony and I both smile.
“Good girl, sunshine. You felt that. Touch your clit…don’t rub it. Just touch it.” Anthony leaned forward resting his arms on his knees. “Bring your fingers up to your lips and rub the fluid on them…that’s so fucking sexy, sunshine. Now slowly put them in your mouth and suck the juices off.”
She did as instructed and looked like she wasn’t going to be able to withstand much more. Anthony had done an excellent job verbally working her up and getting her mind turned on. Her lips were parted and her breathing had picked up. She was very turned on and needed release and Anthony recognized this.
“Tell us, sunshine. Tell us what you need.”
Anthony was trying to encourage her to be more vocal and tell us what she ached for. She smiled and started to look downward but caught herself. Communication was crucial in this lifestyle and it would be required in our dynamic. She was getting there.
“I…need…” She started but had stopped. She was still afraid to voice what she wanted and needed. And maybe she never even gave her wants a second thought. Not with Howard. Sydney had her needs and desires extinguished for so many years that it was going to take more than a scene to resolve it. I knew Anthony wasn’t going to push her much more though.
She was reluctant and had sucked in her bottom lip and was holding it captive between her lips. Such a shy thing. But I knew that was a sign of her being on the edge. Anthony was mindful of this and moved to the bed. He leaned over the bed and put a finger under her chin and guided her to look at him. I could see her settle in his hands.
“It’s okay, sunshine. I need your lips. I want to taste you when I kiss you.” He framed her face in his hands and kissed her gently. When he pulled away from her lips, she looked dazed. She was caught up in him. “Now tell me, sunshine. What do you need?”
Anthony made a world of difference by going to her, touching her and calming her. It gave her strength and encouragement and she continued to try.
“I need…I need you and Master Colin.” Her voice was soft and it held a tad bit of uncertainty. But, she finally expressed a need. Anthony smiled and then looked over at me, realizing her accomplishment too.
I got on the bed and propped myself up on one arm looking in her eyes. I couldn’t help but smile ear to ear. I was so proud of her. To many it wouldn’t seem like much, but for Sydney to voice a desire was a huge accomplishment. I took her face in my hands and kissed her hard and deep. We had pushed her some tonight and now we needed to ease up.
I reached over and pressed my finger against her clit. She lightly moaned and tried to move her hips but Anthony stilled her.
“Good girl. Get on your back, let your legs hang over the edge of the bed and keep your eyes on Colin.”
“Yes, Sir.”
While Sydney got into position, I could tell that she was tempted to look at Anthony but she kept her head turned so she could face me as Anthony instructed. Anthony leaned over her and braced his weight with his arms on the bed. He started kissing her breasts all the way down to her pussy. When his tongue made contact with her flesh between her legs, she bent in the middle. I set my hand on her stomach to keep her still while she had her eyes on me. Anthony let out a quiet laugh at Sydney’s reaction.
“Sunshine, it’s just me and my tongue. But you’ve already met my tongue.”
While Anthony licked and sucked on her, I tugged and r
ubbed on her nipples that were becoming increasingly sensitive. She kept her heated eyes on me but her back kept arching up off the bed. She was enjoying the sensations and was a gorgeous sight as she gazed in my eyes while Anthony pleasured her. It was intense, erotic and our eyes were glued to each other.
Something shifted in that room with the three of us tonight and it was definitely in a positive way. Sydney trusted us and had faith in us. And above all, she loved us. Was this what Matt felt each time he brought Gina into one of these rooms to play?
I leaned over her lightly and began making out with her while I rolled her nipple in my right hand. I held up my weight with my left arm so she wouldn’t feel trapped. Anthony and I tried to make sure we didn’t press our weight down on her. I think Howard did that to pin her down and make her feel helpless, so Anthony and I were cognizant of that.
While I explored her mouth with my tongue I felt her body still and then she grabbed hold of my bicep and pressed a hand against my chest. I brought my head up so I could look in her eyes. Her eyes were open and there wasn’t a trace of fear. She was on the brink of an orgasm.
“That’s it, baby. Let Anthony make you feel good.”
I brought my mouth back to hers. I wanted to feel her come with my lips pressed against hers. Her breathing became shallow and her hand tightened on my bicep and she released a faint moan into my mouth. I pulled my head back to watch her come unglued. Her head started to toss from side to side and I stilled her by taking hold of her chin.
“Don’t run from it, baby.”
She kept her eyes locked onto mine and I stroked her cheek until she relaxed. Anthony stood and got on the bed on the other side of Sydney. He shed his jeans and boxer briefs before climbing on the bed and started making out with her. Sydney and Anthony could make a sport out of making out. Soon, he was flat on his back and Sydney was partially draped over him. I couldn’t help but rub on her back and ass. That ass was calling my name with those cute dimples that sat above her butt cheeks.
I reached in the drawer by the bed and pulled out a condom and held it out for her. I knew she had a trigger with hearing the wrappers tear open and I didn’t want to risk fucking this night up. She took the condom from my outstretched hand, opened the package and rolled it down Anthony’s length. He lay with his hands behind his head with his neck propped up to watch her. Sydney looked down at his wrapped dick assessing her work.
“Good girl. Now, climb aboard, sunshine.” Anthony took her hands in his and he helped her get in position. “Take your time sunshine. I’m not going anywhere. Go at your own pace but don’t close your eyes and don’t take them off of mine.”
“Yes, Sir.”
There was no hesitation on her part and before we knew it, she was sliding down his shaft. She did it slowly, which was to help her get accustomed to his size in this position, but I knew the pace was torture on Anthony. He survived though. Once she was flush against him another soft moan crept from her lips.
He continued to hold her hands and kept his eyes focused on her. I moved to kneel behind her and pressed my erection against her soft butt cheeks while wrapping an arm around her waist.
“Come here, sunshine.”
Anthony encouraged her to lean over him against his chest and stomach. Mmm, that ass was staring at me now. The two of them were kissing again as I stared longingly at her ass. I took my jeans off to give my erection some room and I positioned myself so I could allow my tongue to do some exploring before the lube got in the way.
While I was giving her a nice rim job, I noticed how much she was grinding down on Anthony. She was right on the edge of an orgasm. I almost had sensory overload from the aroma of her arousal. My hands had hold of her butt cheeks firmly as I continued to lick and poke around. Her ass cheeks fit perfectly in my hands.
I reached over and got some lube and lubed up my finger. Anthony heard the cap from the lube and knew what I wanted to do. He let his hand wander from her lower back to massage one of her butt cheeks. He pulled and tugged on the cheek giving me a glimpse of the tiny hole I wanted. It was all I could stare at.
“Baby, your ass is so sexy.”
I massaged her other butt cheek and let the backs of my knuckles skim the soft skin on her butt right around the crack of her ass. She moaned and pushed back against me some. I took it as a positive response and let my lubed finger rub at her entrance.
“Mmm…oh…Sir.” While I was thrilled at this response, I hadn’t expected such a vocal response from her.
“Keep your hands on my chest, sunshine. Don’t move them.”
“Y-yes, S-sssir.” She was moving at a good pace on his dick while I probed her tight hole gently. Anthony reached back and pulled her butt cheeks apart to help give me more access. I slowly had pushed my entire index finger inside of her. It was so hot and sexy. I was sweating and precum was beading at my head.
“Sir?” Sydney stopped moving on Anthony. Fuck! Did I screw this up? Anthony kept his hands on her butt cheeks while my finger was buried in her ass. Her hands were still on Anthony’s chest and looked to be gripping him firmly. Her knuckles were white and seemed to be clamped down on him. I wasn’t worried about him because I knew he liked it.
“Baby, what is it? What color, Sydney?”
“Green, Sir.”
I was confused. I worried that I had done something to scare her or did something that had triggered a memory, yet she said she was “green.”
“Baby, what do you need?” I asked her.
“More, Sir.”
More? I was proud she was expressing a need and a want but I chuckled and shook my head. Did she realize that she already had my entire finger?
“Baby, there’s no more left. Your sexy little ass has already gobbled up my entire finger.” I wiggled my finger making her ring of muscles tighten down on my finger. Anthony and I were enjoying a small laugh and we barely heard her assemble a set of words that were music to my ears.
“Your cock, Sir.”
What did she say? My cock? Was she asking for my cock; in her ass? The contained fire that was simmering in my stomach exploded into an inferno. I think I stopped breathing which caused my head to stop comprehending.
“Baby,” I started.
“Please, Sir. I...I want to try. I trust you both.”
I looked over her shoulder at Anthony. I knew he was looking intently in her eyes and knew that Anthony would give me a clear indication of what he saw in her eyes. Soon, he nodded and kissed her forehead.
“Sunshine, do you want to climb off me so you can take Colin up your sweet little ass?”
She shook her head frantically and continued to move on Anthony.
“No, Sir. I want to be filled with both of you.”
She was so turned on, her fears are less and she wouldn’t feel as much discomfort. She was brave. Our brave fragile kitten. I grabbed a condom and rolled it on. I lubed myself generously and dripped more lube over her tight hole and massaged it in.
“He’ll go slow, sunshine. You tell us if it becomes too much. What do you say if you want to stop?”
“Red, Sir,” Sydney said eagerly.
“And if you need to slow down, sunshine?”
“Yellow, Sir.”
“Good girl.”
Anthony went back to kissing her and tugged her butt cheeks apart. Holy fuck, I was beside myself. She would envelope my dick soon.
My heart felt like it could burst. I was so pleased that Sydney was willing to try this. I knew she had been hurt with anal sex, but she was willing to try it with us. She was brave enough to push her fears to the side and take a chance.
I rubbed the head of my dick over her tiny entrance for a few minutes. She looked sexy, leaning over Anthony while he held her butt cheeks. Finally I pushed my head in just a bit and she tensed up.
I was met with resistance of course. It’s only natural for the body to react like that. She was breathing a little harder now as I began to slice into her. I took a deep breath to help
calm myself and forced myself to go slow.
“Relax, sunshine. Let me see your eyes.” Anthony paused and I had stopped pushing and moving. “Good girl. Now breathe and relax. Just you, me and Colin.”
After a few moments, I could feel her relax and I was able to edge in a little deeper. I decided this was far enough for my dick tonight. Double penetration was new for her, I think, and if it wasn’t, I’m sure this was her first pleasant experience. For the most part I stayed still but Anthony had worked into a nice rhythm.
Sydney’s breathing was definitely more labored and she was warm to the touch. The air was filled with the sounds of our heavier breathing and grunting. Anthony and I were both sweating and it looked like Sydney might be taking chunks of Anthony’s skin off with her grip on his chest. He told her not to take her hands off his chest and so far she’s been able to follow those directions.
I kept my hands on her hips to keep me in place and to help control her movements on Anthony. Her breathing grew shallow and a quiet sound consistently came from her. She needed to let go.
Anthony took hold of her hips and lifted her off him just slightly and then he began to thrust in and out of her quickly. I stayed still but felt everything.
“Ahhh! Oh…Anthony! Colin!” A few additional muffled moans and noises made their way out of her mouth. I felt her ass ring grip me tightly just under my head as her orgasm caught her off guard. As her ass throbbed and pulsed around me over and over, I came so fucking hard. All of this set Anthony off and I felt her tighten again and then Anthony swore as he tried to arch upwards.
“Fuck, sunshine!”
Sydney began twisting and writhing as her orgasm ripped through her. It was wonderful to watch her come and enjoy her body. Anthony and I held her still while we all rode out the orgasm wave.
Sydney had come so hard that she was shaking and I could see her hands quivering on Anthony’s chest. Anthony released Sydney’s butt cheeks from his hands and covered her hands on his chest. He guided her head to rest on his chest. I leaned over her and let my forehead rest against the center of her back while I tried to compose myself. The magnitude of what the three of us just did wasn’t lost on me. Sydney trusted Anthony and I unconditionally. I loved this girl.