Her Secret Santa

by Kelli Callahan

  Elly: Maybe one day you won’t send me home with wet panties and find out. :)

  Ian: Wow, you are certainly in a naughty mood tonight.

  Elly: That’s our fault. You started it.

  Ian: I suppose I did.

  Elly: Then you didn’t even have the courtesy to finish it.

  Ian: I hope you’re not really upset about that.

  Elly: I’m not. :) I’m just teasing you…

  Ian: Good. I really do think it’s best to wait, but that doesn’t mean I wasn’t tempted…

  Elly: Of course, you could be looking at this right now…

  A couple of seconds passed, and then the screen indicated that I had a picture from Elly. I was actually scared to click on it, not because I didn’t want to see what she had sent me, but because I was scared that it was going to make me really regret the decision I made earlier that evening. I finally gave in, and when the image flashed on the screen—I saw a picture of pink cotton panties lying on what appeared to be the floor of her apartment.

  Ian: Oh wow! I’m going to need a cold shower before bed if you keep this up.

  Elly: I’m planning to soak in a tub of ice water. :)

  Ian: I don’t think that’s going to get you off Santa’s naughty list…

  Elly: I think it’s worth a little coal in my stocking. It’s not like I was planning on getting any actual presents…

  Ian: You might be getting the other thing that Santa leaves for naughty girls. A stocking full of switches!

  Elly: I don’t think I’ve heard that one…

  Ian: Ah, you should look it up. :)

  Elly: One second…

  I wasn’t surprised that Elly hadn’t heard about the other thing that Santa could leave in lieu of coal. It was kind of a joke that my grandparents used to tell me, and my grandfather swore that he actually got some one year when he upset his parents shortly before Christmas—he never told us if they actually got used or if it was meant as a joke.

  Ian: Find it.

  Elly: Oh hell no!

  Ian: Ha! I guess you did. :)

  Elly: I’m going to put my panties back on right now!

  Ian: It’s too late for that now. Santa Claus is always watching. He knows when you’ve been naughty or nice.

  Elly: I knew there was a reason I didn’t like that guy.

  Ian: There’s only one way to save yourself now.

  Elly: Oh yeah? What’s that?

  Ian: Click the button and make me your Secret Santa. I’ll make sure you don’t get switches or coal.

  Elly: This feels like extortion.

  Ian: You’re the one that decided to be naughty this holiday season.

  Elly: Fine… I guess we can play Secret Santa if you really want to.

  Ian: You finally have a little Christmas spirit?

  Elly: No, I have Christmas fear thanks to you!

  Ian: You’re hilarious.

  Elly: I was planning to click it anyway after our not-date tonight.

  Ian: Then it must have been a really good not-date. :)

  Elly: I thought it was…

  Ian: Me too.

  Elly and I talked for a little longer before we were both ready for bed. There was a little more teasing, but nothing that was very dirty—just a good bit of flirting. I finished the last of my whiskey and went upstairs. I really did feel like I needed a cold shower, even though I was pretty tired. My head was still buzzing from the excitement of the evening, and my cock was partially engorged from our conversation. All it took was one thought about those pink cotton panties on Elly’s floor for it to start getting hard again.

  There’s no way I’m going to be able to go to bed without doing something about this.

  I walked into the bathroom and started the shower, but instead of setting the water to the right, I turned it to the left and let it get warm. I stripped off my clothes and stepped inside. It really did feel good. A cold shower would have probably made me stay awake longer, but a warm one would be rather relaxing, especially after I took care of the problem that wasn’t going to go away on its own.

  I really was tempted to drive Elly straight back to my place instead of dropping her off. Damn, and she’s a virgin? Fuck…

  My hand slid down to my cock, and I started to rub my length. All it took was a couple of strokes for it to fully engorge. I couldn’t remember the last time I had been that turned on. Abigail was my first, and no woman had shared my bed since her—none of my attempts ever went further than the first date. I thought about just finding someone to get it out of my system a few times, but I never worked up the courage to go through with it. I was in a very long drought, but it seemed like that was about to change.

  If I close my eyes, I can still feel her lips on mine and her curves against my fingertips.

  My strokes started to pick up speed, and I felt a pressure in my balls. My thoughts started going to a very dirty place. I imagined Elly’s lips moving away from mine—down my abdomen—with every intention of doing something that she had probably never done before. Her lips were so soft, pouty, and perfect. They would feel amazing on my cock. My hand was a weak imitation, but I could pretend. I imagined my cock going into her mouth, and my balls twinge with anticipation of how good it could be.

  I would want so much more than that…

  My thoughts shifted to Elly’s naked body on my bed—my lips teasing her skin as I prepared to pop her cherry. I had never actually been with a virgin before. I wasn’t the first guy Abigail had ever been with, and she obviously knew more than I did. It would be different to be on the other side of that with a virgin’s timid touch waiting to be guided towards the pleasure that could be brought to life when desire gave way to primal passion and lust. I imagined my cock moving towards her pussy—ready to claim it as my own.

  God, I’m gonna cum before I can even imagine myself inside her…

  I started moving my hand faster. I was at the point where I couldn’t turn back, even if I wanted to. All I could do was give myself a few more pleasurable strokes before I erupted. My balls got tight, a loud gasp rushed from my throat, and then I felt the cum surging through my shaft. My dick throbbed and pulsated in my hand several times before I started to spill my seed. I ejaculated all over the shower wall, and then the last of it started to get mixed in with the water from the shower that was running down my body.

  It’s definitely time for this drought to end.

  I stood there underneath the water until my head stopped spinning from my climax, then I reached for the soap and started lathering up. It was nice to blow my load, but I didn’t feel satisfied. It was just a pressure valve that desperately had to be released. If Elly had been there with me, once wouldn’t have been enough. I finished my shower, and my cock was still partially engorged when I turned off the water. It wasn’t satisfied either—my hand was a terrible substitute for the real thing—or maybe it was just difficult to settle for that when I knew there was a woman that wanted me as much as I wanted her.

  I may not be able to resist the next time she’s in my arms—even if I want to take things slow.

  I dried off, put on a clean pair of boxers, and walked to my bedroom. I finally felt relaxed enough to sleep. I wasn’t sure if my mind was going to give me much peace when I finally did close my eyes. It was still racing with thoughts of Elly and the things I wanted to do to her. I reached for my phone and realized that I had received quite a few messages from Elly while I was in the shower. The first one was confirmation that she had accepted me as her Secret Santa. The second was a picture of—what appeared to be her panties, almost covered by her dress—followed by one of her bra. My cock started to get hard again as I scrolled down to the actual messages.

  Elly: Guess what I’m about to do?

  Elly: I’m going to be alone, but I’m not wearing anything at all…

  Elly: You must be asleep…

  Elly: I can be naughty now that you’re my Secret Santa, right? I don’t have to worry about a stocking full of
coal or switches…

  “Fucking hell…” I stared at the screen in disbelief.

  I guess I’m not the only one that needed something to take the edge off before bed…

  Chapter Eleven

  Elly

  My conversation with Ian left me with a smile on my face and a lot of dirty thoughts in my head. There was no way that I was going to be able to go to sleep without giving myself a date night. Oddly enough, I would probably need a new name for it since I was seeing someone—or maybe I wouldn’t even need to take care of the problem myself if things continued in the direction that they seemed to be heading. Regardless of what I ended up calling it in the future, Ian wasn’t there, so the only choice I had was to take myself to bed.

  I can have a little fun in the process. He might still be awake…

  I hit the button to confirm that Ian was my Secret Santa, and then I sent him a picture of my dress on the floor. The dress was too expensive to leave laying there, even if I was horny, so I tossed my bra next to it for another picture and gathered everything up. There was no response from Ian, so I sent him a few messages, which also went unanswered. He must have been able to go right to sleep when his head hit the pillow, but there was no way that I was going to be able to do that. I was so turned on that it felt like I had a fever.

  I guess he’s just going to have a few dirty messages when he wakes up tomorrow.

  When I first got my apartment, date nights were a big deal. I didn’t have a boyfriend, nor did I want one, so I would go all out. A bubble bath, a glass of wine, soft music, and I even had some sexy lingerie that I wore if the mood struck me right. Some would have probably said it was a silly thing to do, but it was my version of a sex life. There was no time for any of that—I was way too excited for self-indulgence or foreplay. I just needed to make myself come so I could go to sleep. I didn’t think that was going to take long at all.

  This will be different. I have a real person to think about…

  I put a towel on the bed, stretched out on it, and bent my legs at the knee. I normally teased myself a little bit before my finger got all the way to my clit, but I didn’t need it. I moved my hand down my abdomen and rubbed my clit with my finger. I was so turned on after my evening with Ian and our dirty talk on the app that I was extremely wet, and some of that had spread all the way to my clit. I moved my finger in a circle around the hood and felt the pleasure sweep through my body. It had been so long since I brought myself to bliss that I practically orgasmed before I got a rhythm going.

  Hopefully, the next time my panties are wet when they come off, I won’t be alone in my bed…

  I imagined Ian’s lips against mine—the kiss we shared shattered my reality for a moment before the pieces came back together. His arms felt like the place I had always belonged. That closeness made me feel so warm and wanted. If he could make me feel that good with a kiss and a tight embrace, I couldn’t even imagine what it would be like when the heat really got turned up. He was definitely the guy I wanted to lose my virginity to, and I didn’t care if we hadn’t known each other very long—being with him made me feel things I had never felt before, and I wanted to experience all of my firsts in his arms.

  I never wanted to sleep with any of the guys I dated—even when they pushed for more than a kiss at the end of the night. After my not-date with Ian, I was the one pushing…

  I never viewed my virginity as a prize that some guy got to win—but I wanted Ian to claim it as his own. I wanted to see the desire that raged in his eyes before he forced himself to pull away—I wanted it to burn with the intensity of a thousand suns when he was inside me. I didn’t just want him—I needed him. I never imagined feeling that way about a guy, but Ian was no ordinary man. He was a diamond in the middle of the city that seemed to have lost the shimmer it used to have. The next time we were together, I was going to make sure it was impossible for him to pull away. I wanted to give him so much more than my heart.

  He may have already run away with that…

  My finger kept moving against my clit. There was a pressure building up inside me. I slowed down so that I could enjoy the build a little more. I was eager to come, but I was enjoying the fantasy. When I was in Ian’s arms, I could tell that he had a strong physique—I couldn’t wait to see what his suit was hiding. He might have been the master of dad-jokes, but he definitely wasn’t rocking a dad-bod. I didn’t care if I wasn’t the first woman to see it—I had every intention of being the last.

  Oh god, I’m gonna come…

  A moan started to echo in my throat, and my finger moved faster against my clit. I was almost there. I could feel myself moving close to the edge. My body was screaming for the release that was on the horizon. I threw my head back, closed my eyes, and felt the pressure mounting—then there was a buzz beside me. My eyes opened, and I looked over at my phone to see a message from Ian. I immediately pulled my finger away from my clit like I had just been caught with my hand in the cookie jar—but a smile spread across my face when I read the message that he sent.

  Ian: What are you doing, naughty girl?

  Elly: Thinking of you…

  Ian: Just thinking?

  Elly: I might be doing a little more than that. :)

  Ian: You’re going to be at the very top of Santa’s naughty list this year.

  Elly: If you’re my Secret Santa, then that’s exactly where I want to be.

  Ian: I don’t have to bring you a stocking full of switches to do something about that naughty behavior…

  Elly: Oh? What are you going to do? Spank me? :)

  Ian: I just might…

  Elly: If you were here right now, I’d let you. Trust me, I more than deserve it…

  Ian: I know. I saw the pictures…

  Elly: What were you doing anyway? It took you a really long time to respond.

  Ian: I took a shower.

  Elly: I decided to skip the cold shower.

  Ian: Mine wasn’t cold.

  Elly: Were you being naughty too? :)

  Ian: Maybe…

  Elly: Too bad. I could have given you a much better picture if you asked. Then you wouldn’t have had to use your imagination.

  Ian: You can still send me one.

  Elly: Will you be naughty again if I do?

  Ian: Probably so.

  Elly: I want a picture in return…

  I put my arm across my breasts, pulled the top of the quilt over my abdomen, and took the dirtiest picture I had ever taken before. My finger trembled when I got ready to send it. I was putting a lot of faith in Ian with a picture like that—but I didn’t care. I hit send and waited for him to respond. There were a couple of awkward seconds where I wondered if he was expecting something tamer, but then my phone lit up with a picture from him—and I burst into laughter when I saw it.

  Elly: Really? You copied my pose!

  Ian: Your pose was hot.

  Elly: Yeah, for me!

  Ian: You don’t like my picture?

  Elly: I’d like it a lot more if your quilt was moved a few inches to the left.

  Ian: You’ll have to wait to see that in person…

  Elly: Are you busy tomorrow? :)

  Ian: Will you go on a real date with me?

  Elly: Yes.

  Ian: Then my schedule is wide open.

  Elly: Then it’s a date.

  Ian and I talked for a few more minutes before we said goodnight for the second time. I flipped to his picture and stared at it. It was comical since he tried to mimic the pose I was in, but there was more than enough material for me to finish what I started before I got interrupted. He definitely had a muscular physique, and it was more impressive than I imagined. He looked like a Greek god that had been chiseled from stone and brought to life. My finger moved back to my clit, and I started rubbing with more intensity than before—I barely made three rotations before I hit the point of no return.

  God yes!

  My legs started shaking, my muscles got tight, and then a surge o
f pleasure shot through my veins. I orgasmed so hard that my body felt like it was going to start convulsing. There wasn’t much of a peak—it was like an explosion of lust that started and ended with a bang. I rubbed until the orgasm faded and then put my phone down on the table beside me. The need had been quelled, but I was still a little wired—my excitement was heightened by Ian’s picture and the thought of another date with him.

  Once will not be enough. I think I’m going to need round two…

  I waited a couple of minutes to see if the feeling would pass, but it just seemed to get stronger as the seconds passed. My finger moved back to my clit, and I started rubbing again. I didn’t think about Ian’s impressive physique or the way he made me feel—it was a lot more savage than the first time. I imagined him between my legs—our bodies slamming together as we chased our mutual desires. It only took a few minutes for the pressure to build, and then the second wave of bliss consumed me. The orgasm wasn’t as strong as the first one, but it still made my body shake. My head spun after it was over, and the afterglow finally calmed me down.

  I think I can go to sleep now, but I have a feeling that Ian is going to be in my dreams—there definitely won’t be any sugar plums.

  Chapter Twelve

  Ian

  I got the best night of sleep that I had gotten in years and woke up feeling rather refreshed—partially because of what I did before I went to sleep and partially because I had Elly’s beautiful smile in my thoughts all night long. The first thing I did was reach for my phone and read through our conversation. I didn’t need a reminder to remember what we talked about, but it was still nice to read the exchange. By the time I finished, my cock was hard, and I was thinking about turning our conversation into reality.

  I’m so tempted, but we should wait before we take the next step in our relationship. It needs time to flourish first.

  Somewhere in the midst of flirting, teasing, and talking dirty to each other, Elly and I made plans for a date. I needed to figure out where I was going to take her and make plans. I fixed a pot of coffee, pulled out my phone, and started doing a little research. It had been a long time since I planned an actual date, so I was rusty on current events that didn’t involve global politics or business—the former was my grandfather’s specialty, and the latter was mine. I found a few things that were interesting and jotted them down.