by Sera, Drew
I handed him another condom from the bag and he held it in his hands for Sydney to help him open. Given her first reaction to the sounds of them being opened, I thought that was a great idea for him to have her help get it on him. He lifted her up so that she hovered over the tip of his dick and then she slowly slid down the length of him. He leaned his head back and smiled at her as I reached for some lube and lubed up a finger really well.
From experience, I knew that if a sub had had a bad prior experience with something, that they were less likely to ever go back to it. So I was trying to test the anal waters and see if it was a possibility with Sydney. If not for me, then it’d be good information for Evan to know. Or any potential Dom. The thought of her playing with another Dom other than Anthony or myself, made my stomach hurt though.
Anthony brought his knees up, which pulled her butt cheeks apart some. To give me easier access, he pulled her cheeks apart further with his hands. She was fine with this and it wasn’t until she felt my lubed finger beginning to rim her backdoor entrance that she made a noise and tried to turn around to see what I was doing.
Her forehead was creased and she was frowning. She didn’t appear to be afraid, but was wary and cautious.
“Easy, sunshine. He’s not going to hurt you. He just wants to see if you like something.”
Her body tensed and she hardly moved on top of Anthony anymore. I knew this was because of my probing finger. I was angry because I know Howard probably fucked this up for her. She was obviously scared of it hurting and I didn’t want to ruin the night so I withdrew my finger and propped myself up on a bent arm and tweaked her nipples while she rode Anthony. She looked beautiful as she rode him and enjoyed herself. Her hands gripped Anthony’s shoulders and their gaze was locked onto one another. I was proud of her for letting go and trusting us.
After they came, I got up to get rid of the condoms, wrappers and supply bag. When I got up, Anthony sat up on the edge of the bed and pulled her onto his lap and into an embrace. He had pulled a blanket up around her waist and showered her face with kisses. They were in their private place and didn’t see me take a picture of them with my cell phone. It was an incredible picture of them and didn’t show any nudity other than Anthony’s back. Sydney’s head was resting to the side on his shoulder facing his neck. It captured their connection and bond with one another.
When I climbed back on the bed, Anthony set her in the center of the bed between us and we both cuddled her. At first she was uncomfortable, but once she realized that this was important to Anthony and I, she relented.
Chapter 69
Monday, November 18
Colin
I woke up around 5:15 in the morning to movement next to me. It wasn’t panicked, nightmare thrashing movement but rather flirty in nature. I kept my eyes closed but was very aware of what Sydney was doing. She was rubbing her butt against my hand and I couldn’t help but smother a smile. Sydney took hold of my hand and was pushing herself against my finger. This girl was something else. She was curious, but afraid to be. I let her explore a bit on her own before I let her know that I was awake.
I slowly moved around and slipped my arm under her pillow and pulled her against me in a cuddly embrace. I smiled against her neck and kissed her shoulder. Her body tensed but then relaxed some as she realized I was just snuggling her. My heart breaks for her though. Her Dom will reach for her in the night and she won’t be expecting it and it’ll scare her. Fucking Howard.
“Good morning, baby,” I whispered in her ear. “You know, my finger would feel much better lubed.”
She stilled and tensed in my arms, embarrassed. I propped myself up but still held her against me and let my hand skim her stomach and looked into her eyes.
“You’re curious, but afraid. Am I right?” I whispered and she responded with a whispered confirmation. “It’s okay to want something like that or want to try it, baby. Have you tried anal sex before?”
“Yes,” she whispered.
“How was it?”
“Um, it hurt. I wanted to like it, but it hurt.”
Typical. Anal sex was one of those acts that if it brought a bad first time experience the chances of going back to it were slim. I was going to try to cure her fear.
“Baby, would you like to try my lubed finger? I promise you that it won’t hurt. I will tell you that it’ll feel different but it won’t hurt. Unlike Howard, you can trust that I know what I’m doing.”
Her intense eyes maintained contact with mine and she nodded.
“Words, baby.”
“Yes, Sir. I’d like to try,” she whispered.
“Okay, baby. You still can use ‘yellow’ and ‘red.’ Lie on your side and face Anthony… good girl, now bend this leg up and lean into the mattress some…perfect.” I lubed up a finger and reached around to massage her breast with my left hand. Her back was pressed against my bare chest and I marveled the way she felt. I was very close to her so I’d be able to feel her reactions.
When my lubed finger touched her entrance, she made a small noise and instinctively reached out for Anthony. No matter what, she felt safest with him and in his arms. I encouraged it.
“Baby, you can hold onto him. He won’t mind. He’ll help.”
All she needed was a little encouragement that it was okay. She wrapped her hand around his bicep while I worked my finger around her entrance. Her soft moans alerted Anthony and he propped himself up on his elbows. He knew by her position exactly what I was doing and he smiled genuinely.
“Sunshine wants her little hole filled,” he said and bent to kiss her.
The minute he put his hand on her other breast and began making out with her, her body relaxed and opened up to me. I slipped in my finger to the first knuckle and she moaned but followed it up with saying ‘yellow.’
“Okay, baby. Yellow it is. We’ll go slow. Try to relax and let me know when you’re ready.”
I kept my finger where it was and kept it still. She trusted me to accept and listen to her ‘yellow’ warning. If she were to ever warm up to anal play, it would all depend upon how I reacted to her worries and fears. Anthony was still kissing her and he and I each had one of her breasts and nipples in our hands. Soon I felt her begin to push backwards at my finger and before I could ask her if she was ready, she told me as much.
I moved my finger very slowly in her and kept an eye on her face for signs of fear or discomfort. Anthony reached down and inserted a finger in her pussy. Both her holes now had fingers in them and she began moving around.
“That’s it, sunshine. Don’t be afraid to feel good.” Anthony sucked on her earlobe and then looked at me. “Her clit is huge.” Anthony had his thumb on her clit and had two fingers buried in her. She began to move more and moan softly.
“Eyes, baby…Eyes,” I demanded and got to watch them twinkle as she came. She writhed and moaned while she was filled with fingers. It felt incredible to feel her ass muscles clench down on my finger. For a moment, I imagined what it would feel like if it were my dick. I had to be in her.
“Condom, Anth.”
I unrolled the condom and sunk into her soaked pussy causing another moan to quietly escape her mouth. Anthony moved under her and took her face in his hands while he began making out with her again. Her pussy felt so tight on my dick. I wasn’t going to draw this out as I was painfully hard. Ideas of potentially having my dick in her ass had me so hard that it hurt. I quickly found my release and before I had withdrawn, she was coming again.
I was spent and mesmerized by this girl. She was so fragile yet possessed so much power over me. I cleaned up and brought back warm washcloths so I could clean her up. The three of us fell back to sleep and slept soundly until the alarm clock went off at 7:00 a.m.
Chapter 70
Monday, November 18th
Anthony
Fuck me. This girl was doing something to me. On top of which, I was having chest pains along with stomach aches lately. I keep meaning to say something
to Matt but I was hoping it’d go away soon. I think it’s a stomach bug or stress.
I slid out of bed and headed to the shower quietly. I needed to be in the office this morning for a meeting with the finance department at 9:00. I didn’t want to leave Sydney but I knew that Colin would stay home with her. After the incident Saturday, we weren’t about to fuck that up again. Even though our playtime has been tame for Colin and I, it’s been intense for Sydney. Making out was intense for her. She obviously wasn’t used to this kind of play and care and it had easily overwhelmed her.
While I showered and shaved, I began to think about what will happen when Colin is done training her and she starts playing in Irons.
No, fuck that. I didn’t want that to happen. But I was having a disgusting dose of reality this morning. Normally I’m a confident man, but I don’t think I can give Sydney what she needs.
I got dressed in the closet so it’d be a buffer for the noise I was making. I went back into the bedroom for no other reason than to look at her. She was spooning with Colin and was asleep. Colin was awake though and he was looking up at me.
“Anth, what do you want for breakfast? Sydney and I will go make something.”
I shook my head while I tied my tie. “I’ll get it. Stay in bed with her.”
Colin didn’t bother arguing with me, as he knew it was important to be with her and touch her. I wanted to be in bed with her but I took my moody ass to the kitchen and decided I’d skip breakfast. I pulled out a small bag of M&M’s from the pantry and grabbed a sticky note. I drew a picture of the sun and gave it sunglasses and made a caption bubble that said, “have a wonderful day.” Satisfied by my artwork, I headed back to her room and quietly set the candy and note in the dresser where her panties were. She’d find my present later.
“Anth, are you in the office all day?” Colin whispered while his hand lazily rubbed over Sydney’s bruised ribs. I pushed the anger from my system before I let it turn into anything. I wasn’t angry with Colin, but at the fact that she had bruised ribs in the first place.
“Yeah, I think so. I have a meeting with finance and need to work on those quarterly budget reports. With next week being short due to Thanksgiving, I’ll need the extra time.”
He nodded and I headed out to my car. I was in a bad mood now and threw myself in my car and made my way to work. My car felt cold and I wished I could have been back in bed with Sydney.
I grabbed coffee at Beans and had go directly to a meeting. I barely managed to pay attention and could only think about Sydney. Fuck, my stomach hurt. I shouldn’t have put coffee in on an empty stomach.
I had back-to-back meetings that I had to attend and didn’t actually make it to my office until 11:15. I sat down behind my desk and thought about her. Why can’t I get her out of my head? I pulled my wallet out and took out the little glossy black card she gave to me with the cologne. I read it over and over. This little card with her handwritten gratitude means more to me than anything I own. I set it on my desk next to the picture of Matt, Colin and I at a 49ers game last fall.
I wasn’t sure what I was feeling. I loved the way she made me feel. I tore off a piece of paper from my paper block next to my phone and wrote her name in the center and circled it. Then I doodled lines going off the circle, like they were rays of the sun. On the lines I wrote something about her that I loved. I looked down and realized I had just about every ray filled up. Jesus. What the fuck was wrong with me? I ran my hand through my hair and slipped the paper in my drawer. I needed to focus.
I made a few phones calls regarding the Cheng deal and nibbled on a bag of M&M’s that I had on reserve for Sydney. While I was on the phone, Matt sent me a text.
MR: Time for lunch today?
I had time but I wasn’t sure I wanted to go. Last time I saw Matt he shoved his knee in my chest on Colin’s patio. That night was less than pleasant. I knew he felt bad about it though and I had forgiven him.
AG: Are you going to knock me around again?
He answered in typical Dom fashion.
MR: If it’s warranted.
AG: Noon. Vito’s.
I pushed my phone to the side so I could finish a few things before I had to leave to meet Matt. While I was on the phone with the finance manager, my phone chirped again and I glanced down to see it was Sydney.
SB: Hi Sir! I just wanted to say hello and tell you that I really enjoyed last night and this morning. Thank you for the M&M’s. Have a great day and I’ll see you later.
I reached for the phone and felt my chest ache. I temporarily ignored the person on the other end of the phone at my ear to read and re-read the text from Sydney. No woman has ever told me to have a great day or that they hoped I had a great day or that she enjoyed last night. Sydney was killing me.
And what the ever-loving fuck was wrong with me? I started and stopped several response texts to her but decided none of them sounded right. I set my cell phone down and stared out the window while my phone call finished, not that I recalled any of the info that was said during the short conference call. Thankfully James was on the call too. I was useless at my desk until it was time to meet Matt. As I walked to the parking garage I typed a response to my sunshine.
AG: Glad to hear you enjoyed last night. I did too, sunshine. Stay close to Colin today and I’ll see you tonight ;p
I smiled as I hit send and watched the green bar launch my winking smiley face with it’s tongue hanging out to the only woman that takes my breath away. And of course, I thought about her on my drive to meet Matt.
I didn’t want her to be alone but knew better. She wouldn’t be alone with Colin. I knew he was taking good care of her. I could take care of her too.
Wait, what the fuck am I talking about?
Matt already was seated at our usual table on the patio and was sipping on a glass of water when I arrived. I ordered a Coke and reached into the bread basket. Matt was quiet and just sat watching me. Fuck, what was this going to turn into? I hoped one of his big brother/little brother talks wasn’t on my horizon. I sat back in my chair and looked over at him.
“So, how is your day going, Matt? Day off? Out catching some sun?”
Three things happened at that moment. I thought of Sydney, felt my chest throb and remembered that my sunglasses were still at the bottom of Colin’s pool.
“Sorry about your sunglasses and again for the shit I said to you Saturday.”
I waived my hand dismissively at him and looked out over the Strip while I finished my bread and quickly tried to change the subject.
“How’s Gina?”
This pulled a smile from him instantly. He loves that girl dearly. Until recently, I never understood exactly what he must feel like each time he looks at her or heard her name or thought of her. Then Sydney entered my life and I’ve become quite aware of what it feels like to want to give someone everything and anything that I can. My chest began to ache some more and I thought about bringing it up.
“She’s good, thanks for asking.” He paused when the waiter brought over our food before continuing. “She’s getting preparations ready for next week.”
He was referring to Thanksgiving dinner. His entire family was coming in from California and they were all staying with him. It’d be a busy house but he loved them and they were all great people. Matt was lucky to have come from a good family.
“Anth, I wanted to apologize to you about Saturday.”
I held my hand up to try and stop him from continuing. “Matt, it’s not necessary. It’s fine.”
“Shut up and let me talk. You are good for her, Anthony. You really helped her out Saturday. She trusts you.”
And now I felt that we finally hit the purpose of lunch. I shook my head and started to eat my lunch as fast as possible so I could get out from under this.
“Matt, she trusts Colin too and he’s good for her. Why don’t you preach to him?”
“You don’t get it, do you?”
I couldn’t sit through this any
more. I motioned over for the waiter and gave him my card to take care of the bill and tossed my napkin down. I really wasn’t feeling very good now. My chest hurt and I rubbed on it while I loosened my tie.
“Anth, dammit. What are you so scared of? She’s perfect for you. You let her touch your scar for Christ’s sake. She can give you what you need.”
What I needed? What the fuck was that about? I didn’t need anything. Enough of this shit. I leaned forward and tried to keep my voice down while I scribbled my signature on the receipt.
“It’s not about me, Matt! I don’t need anything. And I can’t give her what she needs.”
I got up and left him sitting there. Fuck. Had I known that’s what he wanted to talk about, I wouldn’t have come. I was in enough of a mess now and certainly didn’t need anyone telling me that I was good for her. Could none of them see me being bad for her?
I got back to my office and tossed some ant-acid tablets in my mouth and worked through the rest of the day thinking about Sydney and Matt. I felt like shit. I needed to apologize.
AG: Sorry, Matt. I’m a selfish prick.
MR: I’ve been pushing you too much. I’m sorry. Next week is Thanksgiving and you’re part of the family. My mom has been asking about you and expects to see you next week. Are we good?
Matt comes from a near picture perfect family. He grew up with Colin and their parents were friends. Their dad’s had a psychiatry practice together and Matt’s folks took Colin in when his family died on Thanksgiving. When I became friends with them, I also got a spot in Matt’s family. His parents are very nice and while I think his dad likes to analyze me, his mother is as sweet as can be. I was looking forward to seeing them too.