#FreeSmut: Santa’s Secret Sissy

Romance Author

#FreeSmut: Santa’s Secret Sissy

Copyright 2016

Julia and I had been friends for a long time… so much so we knew our most intimate secrets. We dated once years ago but the spark wasn’t there but we are probably closer than any couple in the world. Our meeting was dramatic as she saved me when I was being bullied in high school. Bullies usually prey on those that are different or those they fear. She really took pity on me and protected me those last few months of high school and we stayed in touch after we went away to different schools.

After college, we returned home and hung out together. She would always talk about her boyfriend and I would talk about my single life hitting the clubs and dating gay men and other “gurls.” I loved Julia. I was jealous of her though because she had something I had always wanted, the physical love of someone. While I dated a lot, it never went beyond making out and a little groping. Julia had the love of her life with her and he gave her everything… it wasn’t long before I knew how much she was being given.

We went out to lunch after Thanksgiving to catch up and the holidays always got me down. I usually spent the time alone while everyone else was with family and friends. Julia knew this and asked me if I had plans for the holidays.

“No, I don’t have anything planned. I thought about going out of town, but it is not the same when you go alone.” I said.

“What about going to see your parents?” Julia asked.

“You know that answer already,” I said, “It’s the same old story.”

“I don’t like it when you’re alone during the holidays,” she said.

“It’s okay, I’m used to it,” I replied.

“It’s not right,” she said.

“Not much I can do about it at least now.” I said, “Don’t worry about me, you go have fun with your boyfriend. I am sure your folks can’t wait to meet him.”

“Why don’t you come with us?” she asked.

“I know you’re trying but you don’t need a third wheel,” I said.

She continued to try and help me through the depressing holiday conversation before she had to head back to work. I went back home and sat around my empty apartment. The next day, I decided to take a road trip and do a little shopping. I walked around the mall and picked out a few things for me, but really didn’t have anything else to buy. The only other person I would be getting a gift for would be Julia. Just thinking about that caused my depression to grow even more. Then I dropped even more when I came up on Santa greeting the kids. Watching the kids excited to see him and tell them what they want for Christmas, made me feel great for them and worse for me because all I wanted was someone to share my life with. So I turned around and started my walk back to the car when I saw Julia and her boyfriend. They were coming out of Fredericks of Hollywood and Julia looked a little embarrassed as they walked out and even more embarrassed when she saw me.

“Hey, what are you doing here?” she asked.

“Same as you, shopping,” I replied.

“You remember Rick,” she said.

“Of course, hi Rick, how are you doing,” I said in the best manly voice I could project.

“Hey, Nicky how are you doing?” Rick asked.

“I’m okay,” I said.

I thought the world of Rick because of how he treated Julia, but I really didn’t know much about him. All I knew was what Julia would tell me and most of that was more of how he was in the bedroom and how sensitive he was to her. If not for the fact that he was straight, he would be perfect and I would love to have him holding me. The thought of that continued my downward spiral, so I made a quick excuse and left.

I made it home and sat in the apartment and cried for what seemed like the rest of the day. The next day I tried to pick myself up and re-energize, so I went to the gym to work out. I was on the treadmill when I saw Rick walk in. He immediately noticed me and came over to say hi.

“Didn’t expect to see you here today.” I said, “I thought you and Julia were heading to her folks’ house.”

“We are, but we are not leaving until tomorrow night,” Rick said.

“And you’re here this early in the morning? Must have been a quiet night last night.” I said sarcastically.

“It was. Julia’s worn out from work and last night all we did was talk about you,” he said.

“Me?” I asked, “She needs to stop worrying about me, I’m okay.”

“You know how she is.” he replied, “but I consider you a friend too and don’t like to see my friends hurting.”

“You’re sweet, but you really don’t know me,” I said.

“Maybe not as well as Julia, but she has told me a lot,” he replied.

“I’m not sure how to take that,” I said.

“Take it as someone who really cares about you,” he said.

We continued to talk for a few minutes and just before I left the gym, Rick had another surprise for me.

“Oh yeah, by the way, I wanted to stop by and give you something later,” Rick said.

“You don’t need to do that,” I said.

“It was Julia’s idea,” he replied.

“Okay, I’ll be home, take care, Rick,” I said as I walked out the door.

I got in my car and started home. While en route, I called Julia at work to find out what was going on. She wouldn’t give me any details but assured me that I would really enjoy it.

“You are not helping me here,” I said.

“It was really Rick’s idea,” she said.

“What was his idea?” I asked.

“We want it to be a surprise,” she said.

“Come on Julia, you know I hate surprises,” I said.

“You will like this one,” she said.

“Fine. What time are you guys coming over?” I asked.

“Oh, I’m not going. I am going to go shopping with my sister,” she said.

I knew they were up to something, but I wasn’t sure what it was. So I straightened up the house and waited for Rick to arrive. It was getting late and after a couple of failed attempts to reach him, I gave up and decided to go to bed. I turned off the lights and headed to the bedroom. About 20 minutes later, my doorbell rang.

“I tried calling you earlier. I wasn’t sure you were coming.” I said.

“Sorry, I needed to pick up something for you,” Rick said as he handed me a wrapped gift.

“Thanks, but you didn’t need to get me anything,” I said.

“Well, that is gift number one… the other gift comes later,” he said.

“What do you mean?” I asked.

“Julia picked everything out, so go try it on and I will explain,” he said.

I had no idea what was in the box and didn’t really know what Rick knew about me so I took the box to the bedroom and opened it up. I was blown away. It was a new blue dress with matching color lingerie and blue suede pumps. I stood there looking at it for what seemed to be an hour, but only a few minutes later I could hear an impatient Rick in the living room.

“So did everything fit?” he asked.

I didn’t know what to say, so I started back out to the living room.

“You’re not dressed.” he said, “Did it not fit?”

“Uh, I didn’t try it on,” I said.

“Why not, go try it on. I’ll wait,” he said.

“Do you know what’s in the box?” I asked.

“Of course, I was with her when she picked it out,” he explained. “She knew your favorite color but didn’t know your size. I was always pretty good at guessing my sister’s size so I took a chance and try to guess yours. I hope I was close.”

“Uh, you were.” I replied, “I don’t know what to say.”

“Don’t say anything, just go get dressed, you and I have a nice evening in store,” he said.

“What do you mean?” I asked.

“I’ll explain after you get dressed, now hurry up and get in there,” he said.

I went back into the bedroom and tried to call Julia, who conveniently was not answering her phone. After a couple of minutes staring at the box, I decided to get dressed. I started with the blue lace panties and bra, then wrapped the blue garter belt around my waist and slid on the tan nylon stockings. Next came the blue dress that wrapped around my body perfectly hugging my waist and accentuating my fake breasts. I then slipped on the pumps and headed to the bathroom to fix my hair and makeup. I had always been very feminine and could pass in public, but this time – in that dress, I really looked beautiful. Rick felt the same way when I stepped out of the bedroom.

“Wow, you look stunning,” he said.

“Thanks,” I said.

“No, you really look great,” he said.

“When did you know?” I asked.

“Julia told me a long time ago,” he said.

“Why didn’t you say anything?” I asked.

“We’ll talk about that at dinner, come on,” he said.

He took me by the hand and walked me to the car and drove me to dinner. At a very nice quiet restaurant, we had dinner and talked for a while. He told me about his life growing up and his relationship with Julia. While we had a great dinner, I still didn’t understand what was happening. Was I really on a date with my best friend’s boyfriend? Should I be expecting more than just dinner? What does he really know about me?

“I have to ask, what did Julia tell you about me?” I asked.

“What do you mean?” He asked.

“I mean, really tell you.” I explained, “Julia and I are friends and have been for a long time, but you really don’t know me.”

“I know that you guys are close and I know how you met and based on what Julia has told me you are probably the best friend she has ever known. Did I miss anything?” he asked.

“Yeah, but to go do all of this for me. It doesn’t make sense.” I said.

“Look, Nicky. I know you are uncomfortable right now and Julia was concerned about you, and when we talked about it, I became concerned too. I consider you as much of a friend as she does.” he replied.

“But you don’t know me,” I said.

“I know all I need to. You’re caring and loving and beautiful and intelligent… stop me whenever you’d like.” he said jokingly.

“No please go on, I love to hear it,” I replied playfully.

“Seriously though. I care about you and don’t like to see anyone I care about hurting,” he said.

We finished dinner and left the restaurant. After getting back to my apartment, Rick had to park on the other side of the park because of the congestion in the parking lot due to the holiday visitors. We walked through the park as it started to snow. During that walk to the apartment, Rick shared something with me. Something I didn’t expect.

“Can I ask you a question?” he asked.

“Of course,” I replied.

“What does Julia say about me?” he asked.

“Let me just say that I can see everything she has described about you.” I said, “I can see why she loves you.”

“Did she tell you about the other stuff?” he asked.

“What other stuff?” I replied.

“I guess not, we did promise to keep that between us,” he said.

“I don’t understand. What are you talking about?” I asked.

Turns out Julia and Rick have been in an open relationship since they met. They tried to be exclusive, but they both wanted more, so while they don’t date a lot, they both agreed that once a month they could see whomever they wanted. It blew me away. Julia had never said anything and I never knew she was that much into sex.

“I never knew.” I said, “I mean, Julia talked about how great you are in bed minus a lot of the details, but never told me about anyone else?”

“We agreed never to talk about it and we always planned it on the same night so it avoided any suspicion,” he said.

“I’m sorry, I don’t know what to say. I am completely blown away.” I replied, “Why are you telling me this?”

Rick hesitated for a quick second. He then stopped walking and turned to me and said, “We always planned our nights on the 24th of each month.”

Now I was really getting scared.

“What are you saying?” I asked.

He pulled me close and kissed me passionately. I started to pull away, but the feeling was so intense I lost control for a minute. I then realized what was happening and pulled back quickly.

“Rick, stop,” I said.

“Are you okay?” he asked.

“You don’t want to do this,” I said.

“Why?” he asked.

“What do you mean why?” I asked

I didn’t understand why he didn’t get it. He knew I was a man and that should have been enough, but tack on to that Julia was my best friend. I didn’t know how this would affect us.

“Look. I know about what is under that beautiful dress you’re wearing.” he explained, “I know that Julia is your best friend, but what you don’t know is that you would not be the first unique girl I have been with and Julia knows that too. The other thing you don’t know is that this was really her idea.”

When I heard that, I started to cry. Rick pulled me close again and wiped the tears from my cheek and kissed me again. Only this time I didn’t pull away, I clutched onto him tightly hoping he would never let me go.

We made it back to the apartment and he immediately began to undress me. As my dress slid down my body and onto the floor, I unbuckled his belt and pulled down his pants. His strong hands had a firm grip on my ass and my lower back and he nearly lifted me up in the air holding me against his body as we kissed.

I then began to kiss his neck and chest working my way down to my knees and his beautiful package. I slowly rubbed his cock through his briefs and watched as his cock grew harder and longer. I then pulled his underwear down and gently rubbed his cock against my face, kissing it softly. I could see what Julia was enjoying because now I wanted all to myself.

I then began to orally satisfy Rick, slowly taking every inch of his enormous cock. We didn’t say much to each other and never once mentioned Julia again that night. I was in heaven as I sucked his cock, getting him nice and wet as I began to stroke myself through my blue panties.

“Oh yeah… Oh yeah, that feels good,” he whispered.

I remained silent as I had a mouthful of his juicy cock.

“Oh my god… yeah…. Suck that cock.” he uttered softly again.

He pushed me back and we moved from the hallway to the living room couch, where he sat and I continued. As I went down on him, I was thinking I wanted so much more. I began to fantasize about riding his hard cock… and I would soon get my wish. He began to shake a bit so I pulled up and began to stroke him waiting for him to cum. He then pulled me forward by the hand so my chest rubbed up against his cock.

Rick then looked deep into my eyes and said, “I really want you.”

I don’t know why I responded the way I did, but I kissed him and whispered in his ear, “I want you inside me.”

We kissed some more and he pulled my knees up on the couch and positioned his cock near my pussy. He poked me a couple of times with his wet cock, then I licked my hand and reached down to wet him some more. I had never felt the real thing before, but I was about to as he slowly slid his rock hard cock inside me.


“Are you okay?” he asked softly.

“OH GOD YES,” I said.

He pushed in a little further and the feeling caused me to lose control and I fell down the rest of the way – taking every inch of his big dick.

“OH… OH… OH, you are so tight. I love your virgin ass.” he said.

“Give it to me baby… FUCK ME…. FUCK ME…. OOOOOOOO… YEAH…. I LOVE THAT BIG DICK INSIDE ME.” I yelled out.

I began to bounce up and down on him. I couldn’t believe the sensation of his cock sliding in and out of me. Rick was a rock in more ways than one. He wanted me to enjoy myself but he knew I didn’t want it to end quickly and I don’t think he did either, so he slowed me down taking slow, long deep penetrations so I could really enjoy every inch of his cock. As he did, I found myself clutching to him, biting at his neck and digging into his shoulders.

He then pulled me up off of him and bent me over the couch and moved behind me. I never hesitated and pulled at my ass so he could see and he pressed his cock against my pussy again until the tip penetrated and then he slid in the rest of the way.


He began pushing in over and over slowly and the sensation was better than when I was on top. I could feel the sweat dripping from him onto my back as he powered through me. As he fucked me I could feel one hand on my hip while his other hand ran up my back to the back of my head. He then grabbed a hold of my hair and pulled me back as he got a little rougher.

“OH YEAH… OH YEAH… YEAH BABY, I love that pussy.” he said.




“I’M GONNA CUM…,” he said.


He pushed in me a couple more times then quickly pulled out and I turned quickly to receive his final gift.

“OH YEAH… OH YEAH…. OH… OH… OHHHHHH.” he said as he shot his load all over my face.

Hitting my cheek, lips, and tongue, I ate everything he was willing to give me. He slowly rubbed his cock against my face as the last few drops of cum dripped onto my cheek. I cleaned him off and I helped him back to the couch where I laid with him with my head on his chest legs over his.

After he drifted off to sleep, I got up and took a shower, remembering every detail of the evening. I returned to sit with him so charged up I never slept a wink. The next morning, Rick got up and took a shower as I was in the kitchen making breakfast wearing only my favorite blue silk robe. He came out of the shower, got dressed and walked up behind me, put his arms around my waist and kissed me on the neck.

I wasn’t expecting anything after the night of passion we had. To be honest, I figured he would have an excuse to leave, but he poured a cup of coffee and sat at the table. We talked for a little while and I had to remind him that he had plans for the holidays.

Like Julia, he asked me to join them, but as I explained to his lucky girlfriend, three’s a crowd. He got up from the table and I walked him to the door. He gave me another kiss and suggested we get together again soon. I didn’t respond but gave him a look that hopefully gave him a clue.

After he left I cleaned up the kitchen and began the rest of my day. About an hour later, Julia called.

“So, did Santa bring you everything you wanted for Christmas?” she asked sarcastically.

I remained silent not saying a word.

“Nicky?” she asked.

“Let’s just say, Santa knows this is the season for giving… and he gave me a lot.”

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One Response

  1. Anonymous says:

    Bookmarking this one for the holidays when I am all alone.

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