Prologue
I became physically attracted to my sister Melissa when she was 15 years old and I was 18. Sis was about 5’2″, baby blue eyes, she had a nice figure with still a little baby fat as they say. Her breasts were 34 C which I knew from checking her bra in the laundry. The thing I found most attractive about her was her long chestnut brown hair which went down to her waist.
Often after she took a shower she would ask me to brush it for her if I wasn’t busy. I actually started to make sure I wasn’t doing much when I knew she was about to take a shower. I don’t think she ever purposely wore anything with the intention of exciting me. I did get to see her in a various stages of dress, long t-shirts girls like to sleep in, her swimsuits both one piece and bikinis, bra and panties, and a occasionally just a towel wrapped around her. My favorite was an old dress shirt of mine I had outgrown she seemed to like to sleep in. She never wore a bra with it and it would be unbuttoned to the point of exposing most of her breasts when she’d sit on the floor in front of me. It also gave me a nice view of her collection of thong panties.
Even though there was never any sexual contact my imagination would come up with some pretty hot fantasies of how things could get sexual between us.
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I am now 46 and Sis is 43. I’ve been divorced for 2 years now. Melissa kicked her husband out after finding him fucking his office assistant at his company’s Christmas party.
I knew from talking to her on the phone she felt it was her fault for letting herself go and getting fat and he didn’t find her attractive anymore. The last time I saw her she was overweight but far from being fat. I told her just that when we talked but convinced her it was nothing she couldn’t get rid of if she watched what she ate and started to work out. She thanked me for being honest with her said she’d try.
Over the next few months we talked on the phone and I could tell in her voice her spirit was coming back up. We never discussed her weight or appearance anymore. She had decided to fly back for Memorial Day weekend. I was really looking forward to seeing her.
A few weeks before she was due to fly in she forwarded me a copy of her airline itinerary. With a note asking if I would pick her up at the airport since her flight didn’t get in until 9:30 PM. She didn’t want to bother our folks to do it since they normally go to bed around that time. Her long time friend Amy who also sometimes picked her up had moved when her husband got a promotion and had to relocate to work in the company’s Midwest regional office. I replied back that I would be happy to pick her up.
I don’t know why but suddenly those memories of her when we were teenagers started to come back into my mind. The fantasies of being with her sexually were not far behind. I found myself in bed jerking off to those fantasies. My dreams that night were of my sister and I having sex but we were not teens anymore. We were both our current ages and she looked the same as I last saw her. After all these years I still wanted her and loved her more than a brother should love his sister.
When I went online to check my email the next morning there was an email from Sis.
“Thanks big brother I owe you big time. I’m not just talking about picking me up either. We can talk about it when I get there. Love Ya, Melissa”
I was really clueless to what she could be talking about. I was her brother she would never owe me for anything I did for her. I did want to do something else for her though. She seemed to be feeling pretty good about herself but I wanted to try something to boost her self esteem even more. What if she were to get some sexy outfits from a secret admirer?
I opened up my web browser to Victoria’s Secret web page and started checking out some of the various outfits. My memories of her wearing my old dress shirt prompted me to look in the sleepwear section first. I found a silk button up sleep shirt that looked like a man’s dress shirt. Instead of getting a plain white one like my shirt had been I picked one with blue pin stripes. Next I started looking for a pair of panties that matched it. Instead of looking at the thongs, I started to look at what they refer to as v-strings instead of g-strings. I added both to my shopping cart. Next I found a matching animal print bra and panty set. Finally I picked out a sheer black baby doll nightie with a matching v-string. I never realized they had hair care products so I picked a nicely scented shampoo and conditioner. I went ahead and purchased the items as though it was Melissa buying them for herself. I used one of those prepaid Visa cards you can buy in the store and use any name with you wanted. I created a fake Google mail account to send the order confirmation to.
Even though I knew the most I would get from this would probably be to smell her hair if she used the hair care products I didn’t care. The thought of her reaction to getting them and that somebody still found her to be sexy and desirable was enough for me.
I got to the airport and checked the arrivals. Her flight had landed about 5 minutes before I got there. The airport wasn’t too busy since she was coming in on a Thursday night to beat the holiday rush. I waited by the security checkpoint to greet her.
I almost didn’t recognize her when I saw her. She was wearing a pair of low cut jeans and a black tank top. Gone was the bulge around her waistline replaced by some nice tight abs and what looked to be a diamond shining from a belly button piercing.
She came up and gave me a big hug and kiss on the cheek. That really caught me off guard because we rarely hugged each other and actually we both always seemed to deliberately avoid it.
“Look at you!, I exclaimed. “You look great. You’re even letting your hair grow long again.” I couldn’t help but take in her beauty even if she was my sister.
Noticing my gaze she turned around a few times so I could check out the new Melissa.
“Thanks bro,” she said kissing me again. This time it was a quick peck on the lips. “I took your advice and started eating better and working out. Once I got rid of the first 170 lbs, (referring to her husband I assumed) the rest was easier than I thought. I just needed the right motivation.” Teasingly she added, “I must have done better than I thought for my big brother to be checking me out. By the way, I think you need to practice what you preach.” She playfully poked my bulging waistline.
Changing the subject before I got myself in trouble I said, “Let’s get your luggage and I’ll take you to mom and dad’s house.”
“I have a better idea,” she replied. “Since they probably are already asleep why don’t we go to Coaches so I can see the old gang there. I know you don’t really go for that but it is Thursday so it will probably be just a few of the regulars. Besides since you don’t drink much, you can be my designated driver.”
Coaches was the neighborhood bar where she used to work before she got married and moved out of state. I almost said no because I was really uncomfortable around people I didn’t know. I thought about it and was thinking by the way she was dressed she was probably hoping to meet up with a guy she once knew. I was happy for her to be getting back in the dating game so I agreed. “Ok,” I told her. “You know you ask so little of me me I can never turn down your requests.”
We got her luggage and walked to the car. I loaded it in the trunk and opened her door for her while she got in. As we were driving to Coaches she spoke, “I really appreciate this Shawn. Who knows maybe you’ll meet someone. It’s been two years since you got divorced. It’s too bad Amy had to move. You seemed to really like going out with her.”
I know she wasn’t doing it on purpose but she was making it difficult for me not to admit my feelings that the someone I wanted to be with was sitting beside me. The only reason I dated her friend Amy is because the two of them were so much alike. I quit seeing Amy is because I came real close a few times to calling her by my sister’s name when we were having sex.
As I pulled into the parking lot I was relieved to see only a handful of cars. Melissa seemed to recognize a few a cars.
“Looks like there are a few people here tonight I know,” she said.
As we walked into the bar, everyone looked toward the door to see who the new arrival was. From what I could see there were about four couples there. A few of the women got up and came over and gave my sister a hug.
“Melissa, what a surprise,” one of them said. “Are you in town for the holiday?”
“Yes, I’ll be staying for a week,” she answered. “Everyone this is Shawn.”
Melissa introduced everyone to me. They were all strangers but I said a polite hello to each of them. We sat down and ordered a few drinks. When I ordered a drink Melissa looked at me with surprise. “I just need the one,” I said for her ears only. She looked at me indicating she understood.
“You found yourself a quiet one Melissa. That’s an interesting change for you,” the bartender pointed out.
“Yes, he is but he opens up once he gets to know someone. He’s one of the nicest guys I’ve ever known,” she told them. She never pointed out that I was her brother. Maybe it was just because it was all couples and she didn’t want to seem out of place.
Melissa spent the next hour catching up with everyone. She told them about her divorce. They seemed glad that she was getting over it and found someone new referring to me I guess. As we were getting ready to leave one couple invited us to their house for a cookout on Sunday.
“Thanks, but we already have plans to spend it with my parents,” Melissa said.
When we left to leave I opened the door for her and she got in. Smiling at me she said, “You’re always a gentleman getting the door for his lady.” Tonight she was right she did seem like my lady tonight. Everyone in the bar thought we were a couple. It felt nice.
As I started to head to take her to our parents house. Melissa said quietly, “Would it be alright if I stayed with you this trip. Mom and dad always try to go all out when I stay with them and I always feel like I’ve been a burden when I leave.”
“Sis, my place is not all that big. Besides I’d go all out to make you comfortable too, just like mom and dad would,” I told her. Deep down I was worried that being alone with her like that would reveal the true type of love I felt toward her.
“I’m not worried about how small your place is. We’ll be at mom and dad’s most of the time anyway. As for you going all out to make your little sister comfortable I expect that. I just won’t feel like I was a burden afterward because you’re not as old as our parents.”
“Ok, sis like I said before I never seem to be able to say no to your requests
Walking into my apartment she looked around while I set her luggage down. It didn’t take long because I lived in a small studio apartment. It had a small kitchenette with a bar type setup to eat at. I living area with with a couch and desk. The TV was set up so I could turn it around and watch it in the bed which was against the far wall. If you’ve ever stayed at Residence Inn it was a very similar layout.
“Well now that you’ve seen it are you sure you want to stay here?” I asked.
“We can make it work. It may be small but it is a lot bigger than the room we used to share when we were little.”
“Well sis,” pointing out the obvious. “We are a lot bigger ourselves now.”
“That we are big brother… That we are…. Now if it is alright with you I need to take a shower and get ready for bed. It’s been a long day.”
She grabbed one of her smaller bags and headed toward the bathroom after I told her where to find clean towels.
While she was in the shower I changed into a pair of sleep shorts and loose t-shirt that I usually sleep in. I also grabbed a blanket and pillow and set it near the couch. Sleeping on the couch would be no big deal for me. I often fell asleep on it watching TV or reading a book and never bothered to get up and climb in my bed. Finally I turned the TV around and put the remote on the nightstand.
“Well that’s a good trick to get a woman into your bed. If she wants to watch TV she has to share your bed,” she said mischievously.
She caught me off guard and I mumbled something about I just thought she might want to watch TV and I was going to sleep on the couch and read for a bit. Then I noticed what she was wearing. She had on the silk sleep shirt from Victoria’s Secret I had bought her. Damn it complimented her new figure nicely.
“Actually, I was wondering if you’d like your old job back,” she said holding up her hair brush. She walked toward me and sat down in front of the couch. As she sat she pulled up the sleep shirt so she wasn’t sitting on it. I could tell she had the v-string on. I had a brief glimpse of her bare ass.
I sat down behind her and took the brush from her hand and started brushing out her hair. It only reached halfway down her back now. The memories and fantasies came back to me. I looked down and noticed she had the top buttons undone and a nice view of her breasts. I kept brushing as I did years ago.
“I can’t tell you how relaxing it feels when you brush my hair for me. You’re the only guy who would ever do it,” she told me.
I really was at a loss for words. Even more so as I noticed her nipples were now poking out against her shirt. I am not sure but there may have now been another button undone because I could now see the top portion of her aureola. My cock was now hard as a rock and I had no idea how I would hide it from her.
A soft moan escaped Melissa’s lips as she started to get up taking me by the hand holding the hair brush.
“Come on big brother, let’s go to bed. Your bed is big enough for both of us and I’m not letting you sleep on the couch.”
Thinking quickly I grabbed the pillow I had gotten and held it so she wouldn’t notice my cock which was now sticking out of my shorts. As she pulled down the covers and climbed into bed she made no attempt to hide the bare cheeks of her ass from my sight. As I got into bed I wondered if all my dreams and fantasies were about to come true.
“Hey sis.”
“What dear brother?”
“I just wanted to tell you I had a really nice time tonight. Your friends at Coaches all made me feel comfortable. Everything about tonight it made me feel,” I stopped not sure if I should tell her.
“Made you feel what? I think I know but you need to tell me,” she prompted.
I swallowed hard not sure I could say it. Looking into her blue eyes the words came out, “Like we were a couple that was dating. Your friends they all thought we were a couple.”
She looked back at me saying, “I know. I felt it as well. I think we both needed a night out like this. That is why I didn’t tell anyone you were my brother. I wanted that feeling as well. Do you have to work tomorrow?”
“Not really. The Friday before a holiday weekend will be slow. What do you have in mind?”
“Take a guess and ask me,” she said playfully.
Things were starting to become clear as to how we both felt. “Melissa,” I asked “Would you like to go on another date together?”
“I would love that Shawn. I think I know where also. Can I surprise you?”
“I like your surprises,” I said thinking back to the way she looked when I picked her up at the airport. There is one more thing though.” I leaned forward and gave her a soft kiss on her lips. “Goodnight.”
Melissa proper herself up on her elbow looking at me with surprise. “Oh shit, I blew it and pushed it to far,” I thought. Then she smiled at me like I’d never seen before.
She leaned forward and returned the kiss lingering for a few seconds before snuggling up to me. “Goodnight Shawn” she whispered into my ear.