Starting Over

by Erin Cristofoli

  We slid into a booth at Jen’s favorite watering hole. I pulled out my phone; I hadn’t heard from Sir in a few days and was beginning to think he was done with me. Though I felt bad to have brushed him off, all in all, I had enjoyed my weekend and got some much-needed rest.

  “Who are expecting to hear from?” Jen asked me.

  “Sir. I’m not sure if I am allowed to contact him first, or if I am supposed to wait for him.”

  Jen grinned. “Babe, there is only one way to find out.” She snatched my phone from my hand and quickly typed a message and sent it.

  “Oh my God, Jen! I seriously am reconsidering our friendship right now!”

  She handed the phone back to me and smiled. “You love me. I know it.”

  My phone dinged. Jen had written:

  Are you there, Sir?

  The responding reply:

  Of course. Missed you on the weekend.

  What can I do for you?

  My heart was pounding. I had never taken the lead with him. Would this get me into trouble? Well, I guess no response wouldn’t be good either.

  I was wondering if maybe you wanted to see me again.

  Did I give you the impression I was done with you?

  No, Sir. I hadn’t heard from you. I was unsure.

  Believe me, I am nowhere near done with you.

  Oh. All right.

  Want to meet up this weekend?

  I can’t. Work obligations. Next week?

  Absolutely. I’ve been thinking about you, Kate. The anticipation of seeing you is making me hard as a rock. What are you doing right now?

  Oh my. Um, actually, I’m out with a friend.

  Well, why don’t you text me when you are back home.

  I think we now have something to discuss.

  All right, Sir. I will message you later.

  “You’re blushing,” Jen observed, startling me back into reality.

  “Sorry about that. I guess I should say thank you for forcing my hand.”

  “No problem. Funny how I seem to know better what to do with your love life than you do! Ha!”

  Our drinks arrived, and Kate raised her glass to mine. “Here’s to you, Kate, to your fucked up, dysfunctional relationship with Sir, and to you refusing to see what is blatantly staring you right in the face.”

  There really was no point in arguing with Jen; she always ended up getting the last word in. We ordered some appetizers and had a few more drinks, and surprisingly, conversation stayed on safer topics.

  When I got home for the evening, I was both excited and nervous. I knew Sir was waiting for my text. Before even picking up my phone, I wound down for bed. When I did, my hands were actually shaking. What did we need to talk about?

  I finally got up the nerve to send the text.

  I am home, Sir. Were you still wanting to chat?

  Immediately, my phone dinged.

  Yes, of course. I wanted to continue our chat from before. We left off that I was rock hard for you. Now what I want to know is, how did me telling you about that make you feel? Don’t be shy.

  Well, it was pretty hot if I’m being honest.

  Honesty always. Did it make you wet?

  Everything you say makes me wet.

  Good. So what are you wearing?

  Well, I was going to bed, so my PJs.

  More descriptive, baby.

  Um, are we having text sex? Isn’t that a little personal?

  Any more personal than real sex? I just know it can be hot as hell.

  Are you afraid of a little text sex?

  No, I’m not afraid.

  Good. Then you have to give me more, baby. How about I go first. I am in my boxer briefs and a t-shirt in bed. My cock is so hard it aches for you. Your turn.

  Okay. I’m wearing a little tank top, no bra, and a pair of boy short panties.

  Are you wet for me? Touch yourself. I want to know

  I reached down between my legs and felt my wet lips, shuddering. This was so hot; I wasn’t going to last.

  Oh yes, Sir, I am so wet for you.

  Good. Take your panties off. I’m pulling my cock out too. I want you to touch yourself.

  You have me so turned on. If I do, I am so going to come.

  Well, I’m stroking it for you. I wish I were inside you.

  Me too.

  Make yourself come... I want to hear you scream.

  If you were here, maybe you could.

  I was so close… I mean, right at the brink, when my phone started ringing. Was it Sir calling? He did say he wanted to hear me.

  “Wow, you have great timing, Sir. I’m so close.” I was practically panting.

  “Uh, close to what, Kate? Sir? Are you all right?”

  Immediately, I wanted to crawl into a hole and die of embarrassment. Of course, Ben picked this moment to call me. Couldn’t I have checked my damn caller ID?

  I tried to calm my breathing. All I had to do was touch myself one more time and I would be set off.

  “Um, sorry, I thought you were someone else,” I said, still sounding breathless.

  “Clearly. Sir? Is that the guy you have been telling me about?” He continued without waiting for an answer. “So, if you were talking to him, what were you... no. Wait a sec... Were you just...? Ah, I don’t know whether to laugh or self-combust by how hot that is, Kate. So you were close, huh? Wanna finish for me? I know we don’t have that type of relationship, but I wouldn’t be against hearing that. In fact, it would make for some pretty amazing dreams for me.”

  He was laughing at me. Great. I would never hear the end of this. “Ugh, seriously, are you twelve? I am not talking about this with you. It’s inappropriate on every level.”

  “Oh, I can definitely prove to you that I am not an adolescent boy, any time you like, Kate.”

  His words shouldn’t have shocked me, but they did. I shook my head. I just needed to get off the phone now. “Was there something you wanted, Ben?”

  “I think what we’re talking about is much more interesting than what I called for.”

  I kept my silence, waiting for him to continue. He sighed and continued after a moment.

  “Fine. I was wondering how the dress shopping went.”

  I rolled my eyes. “You could have asked me that tomorrow.”

  “Okay, fine. I have been seeing you practically every second of the day, and today was strange not having you around. I kind of just felt like chatting.”

  I couldn’t help but be touched by his sincerity. “The dress shopping went great. I found a dress and shoes, so aside from a hair appointment and a manicure, I am ready to go.”

  “Excellent. All right, well, I know you were busy, so I guess I will let you get back to it.”

  “Yeah, thanks.”

  “See you tomorrow then. Night, Kate.”

  “Goodnight.”

  I sent a text, apologizing to Sir for the disruption. The moment had definitely passed for me, leaving me feeling frustrated and on edge. It was going to feel like years until I was able to meet up with Sir again.

  I curled up under my comforter and turned out the light. Maybe some sleep would help. Yeah, not a hope in hell of that happening.

  Saturday had finally arrived, and I was feeling a little nervous. Normally, I would be dreading the event. I found spending time with clients outside of a boardroom incredibly dull, and I could think of a hundred other things I would rather do. However, tonight was different. As I stood at the mirror fixing my tie, a smile played with the corners of my lips; I looked forward to the event for the first time maybe ever simply because I would get to spend time with Kate. She had kept her dress a secret, and it was driving me nuts. I wore a charcoal pinstripe suit, narrowly cut to fit my frame, complimented with a white shirt and a light blue tie. I grabbed the blue rose I had picked up for Kate off the counter and headed out the door.

  As I headed to pick up Kate in the hired limo, I began to think of the past few days. I had been teasing Kate for days about ou
r last telephone conversation, after which she had sent ‘Sir’ a text to apologize. Though I admit I felt a little guilty about having ‘caught’ her, I couldn’t help playing with her a little. On the other hand, maybe a little sexual frustration would do her some good. Maybe it would do some good for me, too.

  I arrived at her apartment and quickly headed up to see her, my excitement palpable. When she opened the door, I was left stunned. My jaw dropped to the floor, and all I could do was stare at her exquisite beauty.

  Kate began to fidget; I didn’t want her to think that she was somehow less than perfect, so I managed to find some words.

  “Wow, Kate. I don’t think you could look any more perfect if you tried.”

  Her responding smile was breathtaking. Kate’s hair had been twisted up beautifully, with wisps lightly surrounding her face. Her beautiful ice blue gown was out of this world. It was stunning and yet not overly flashy, even though it was adorned with crystals, and somehow, I had unknowingly matched my tie to her dress.

  I handed her the rose. “This is for you.”

  Kate’s cheeks blushed the most beautiful color of pink, her eyes peeking shyly at me through her lashes. Her fingers brushed my own softly, sending sparks through me. “Thank you.”

  I watched her place the rose in a tall glass of water, and when she returned to me, I held out my arm for her. “Shall we?”

  She locked her door before sliding her arm through mine. As we waited for the elevator, I took the opportunity to look at Kate a little more. I had never known anyone who could look as striking as she did in that moment standing there beside me. She returned her hand to my arm and I placed my other hand over hers before leading her to the waiting car.

  When we arrived at the party, I exited first and came around to help her out. I caught a glimpse of her shoes. “Nice,” I said breathily. My mind went into overdrive, picturing what it would be like to have those wrapped around me, pressing into my back as I... Squeezing my eyes shut, I tried to get the image out of my head and halt the blood quickly flowing to my cock. This was hardly the time to sport wood.

  When I opened my eyes again, Kate was looking up at me, a cheeky smile on her lips, her eyes sparkling. “Glad you approve.”

  Laughing, I pulled her into the party, where clients immediately descended upon us. Kate remained on my arm patiently, but all I really had hoped for was to get us to the bar.

  Somehow, during the following 20 minutes, Kate and I were separated. I looked over at her, finding an older gentleman, whose name I couldn’t remember at that moment, had Kate in a deep conversation. I, myself, was discussing the stock market with three other gentlemen. When I looked over at Kate again, she was nowhere to be found. I excused myself from the group and began a walk around the room, being stopped here and there to shake hands and exchanged pleasantries.

  The dance floor was busy, and it was there I caught a glimpse of Kate’s dress. I made my way to the bar and grabbed us each a glass of wine. Wading back through the crowd, I finally reached her, my date. I liked the sound of that. The song had just ended, and I cleared my throat to get her attention. Kate looked up at me, a little relieved. The gentleman she was with thanked her for the dance and made his way back through the crowd, probably to his wife. I handed Kate a glass, and she again took my arm.

  “We should find our table. Dinner is going to be served soon.”

  I was grateful to have picked the other guests who would join us, choosing ones whose company I was sure we’d enjoy and who I was sure Kate would truly shine with. Filling her in on who was who as they approached the table, my longest client, Mr. Kent, and his wife joined us first. We exchanged a firm handshake. “Mr. & Mrs. Kent, how nice to see you this evening. Mrs. Kent, you look lovely as always.”

  A new potential client, Mr. Allen, and his wife also joined us. “Mr. Allen, thank you for joining us this evening. This must be your wife. It’s nice to meet you. I would like you all to meet Kate. You have no doubt had many a conversation with her already since she has started with me.”

  “Ah, Kate, it is wonderful to put a face to the name.” Mr. Kent smiled at her warmly.

  “It’s really lovely to meet you all. I have been looking forward to meeting you for some time now.”

  We all took our seats as dinner commenced. Dinner chatter was light, and I actually enjoyed the company of these men; they weren’t stuffy or stuck up, as I found many of the others in the room to be. The other two men began discussing their golf game. I definitely was not a pro in this particular sport, but as I found myself attending ‘meetings’ on the green sometime, I had forced myself to become familiar at the very least. The women were chatting about something else entirely – a country club I think I heard one of the women say. Kate looked a little lost, but she held her own. In fact, my attention was swayed to their conversation when I heard Mrs. Allen invite Kate to join them at the club sometime.

  I smiled to myself. I rarely attended the country club, but I could see myself doing so if Kate were going to be there. She took that moment to look up at me with a smile, my heart skipping a beat.

  Dinner was stellar, as it was every year, and we ate so much; I wasn’t sure it was healthy.

  When everyone was wined and dined, the music picked up a bit, and Mr. Kent asked Kate if she cared to dance. Kate was perfectly charming and accepted. I asked Mrs. Kent, and we all went to the dance floor. As we circled the room, Mrs. Kent chatted pleasantly, but my attention was really on Kate. She looked so carefree and happy.

  “All right, Mr. Hyde, if you wouldn’t mind heading us in the direction of my husband, I think he has hijacked your date for long enough. I am sure you are looking forward to spending a little time with her all to yourself.”

  I felt myself blush, unsure what to say.

  “I can see it,” she continued, as if reading my mind, “the way you look at her. She is a beautiful woman. I’ve always wondered why you never brought a date like Kate to these events before, but I see now that you were just waiting for the right one.”

  “Kate and I are just friends, Mrs. Kent, but she is breathtaking.”

  Mrs. Kent laughed at me. “You would have to be blind not to agree with me, young man. You may be friends now, but I see good things for you. Hang in there.”

  We came up along side of Kate and Mr. Kent, and we smoothly switched partners. Kate was finally in my arms, and I wanted us to stay just like this for the rest of the night. She fit against me perfectly; she had to see that. “I thought I wasn’t going to get to dance with you at all.” The music turned slow, so I pulled her a little closer.

  “Uh, Ben, people are beginning to look at us,” she stated nervously, biting her bottom lip.

  “That’s because I don’t usually dance at these things.” I couldn’t look away from her mouth.

  “So, why are you now?”

  “Ever since you answered your door tonight, I have wanted to hold you in my arms and dance with you. I would like to do so for the rest of the night.”

  “You might like that, but I’m pretty sure your clients all would like to get a word with you before the night is over,” she pointed out.

  I glanced at my watch and sighed. “You are right, of course. We should get back to business. Come on.”

  We spent the next two hours chatting with the many other clients and coworkers that had attended. I managed to sneak in another dance with Kate, though. It was then that I looked at my watch again. “I would love to continue this dance, but I have to go back to the table and speak with Mr. Allen. I am hoping I can get him to confirm that he will be signing with us.”

  As I led Kate from the floor and we reached our table, she pulled me close to whisper, “I have an idea. You should ask Mrs. Allen to dance. I will ask Mr. Allen. Divide and conquer.”

  I wasn’t sure that Kate knew what she was getting into, but I agreed. A little while later, Mrs. Allen excused herself from my company, so I headed to the bar where I met with Kate and Mr. Allen.

>   “Ben, this woman is a keeper. She has done all in her power to keep me happy, and I like that. But she’s smart, too! Thank you, Kate, for allowing me to monopolize your time and for sharing some drinks with me. Monday morning, we will iron out the details so I can see that presentation, all right? I trust you will be able to come north to my office?”

  I nodded quickly in agreement. “Thank you, Mr. Allen.”

  He shook my hand. “I’m going to find my wife. Enjoy the rest of the night, you two.”

  “Thank you again for coming, Mr. Allen.” I turned to Kate. “So, you seem to have impressed everyone you have come across tonight, not that I ever doubted you. Good job.”

  “Thank you. Uh, Ben, I think I need some air. Mr. Allen enjoyed feeding me drinks. I already feel a little tipsy, and I’m sure it hasn’t even hit me yet. Really, I think I should get going home.”

  “I’ve done my rounds, so I’m good to go home, as well. Just let me get our coats and we can go. Are you all right to stand?” Kate nodded slowly. I wrapped my arm around her waist and led her to the doors.

  When we got outside, I think the booze finally hit her. She swayed and leaned her head on my shoulder. After I helped her into the car, her head returned to my shoulder, her eyes closing.

  “You doing all right there, babe?”

  “Mmmmm.”

  I chuckled; she was definitely toast. We arrived at her apartment a short time later, and I helped her out of the car. Picking her up, I made the trek up the stairs, setting her down at her door.