My Sister's Valentine free porn video

“You bastard! Don’t you dare tell me you love me! You better hope Miss One-That-Got-Away puts out because we’re done! Lose my number then go drop dead asshole!” My sister smashed the hang up icon and threw her phone onto the couch. She collapsed into the loveseat and her eyes started filling up with tears.

“I’m done with men”, she sobbed.

I snuck up behind her and grabbed her underneath her arms spinning her around. I wrapped her in a huge bear hug.

“C’mon sis, you gotta keep dating guys. I can’t go around beating up women who treat you badly,” I said with a smile.

I had hugged her tight enough that her head was buried in my shoulder. I heard a muffled squeal and loosened my grip.

“JAKE! You’re home!” she squealed again and did a little dance. It had the effect of rubbing her body all over mine and I was suddenly aware of the difference between a sixteen year old sister and an eighteen year old sister.

I let her go and looked at her. She had grown into a gorgeous woman. Her delicate Ukrainian features were somehow highlighted by the baggy sweatpants and oversized Central Michigan sweatshirt she was wearing. The little dance she did made me think that she wasn’t wearing a bra. Last time I threw her clothes in the washer I noticed she wore a 32B bra. Being a guy I wasn’t sure what that meant I just knew that her tits fit her frame excellently.

“Yup I decided to see how the family was doing without me. Why are you home? Shouldn’t you be in school?” I asked.

“UGH, it’s my time of the month and my cramps were horrible this morning. I decided to skip since I only have the one class I have to worry about” she replied.

She was a senior in high school this year and was seventh in her class for GPA. She ran cross country which helped keep her already trim figure, fit. A day of playing hooky was not going to hurt her one bit.

“Mom and dad are still death on you going on the pill?” I asked with a wry grin.

“Ugh, don’t get me started. They know I am having sex, they just don’t want any more foreign chemicals coursing through my body than necessary,” she said this last part in a terrible imitation of my dad.

I chuckled. Mom and dad were what I call Generation X hippies. They both drove hybrids, they both shunned any GMO food. We bought all our beef and chicken from a local farmer. Thankfully they weren’t overly into holistic medicine like some of their friends. When I broke my wrist they took me to the doctor. They weren’t quite crazy, just very liberal.

“Okay so tell me why you were crying and thinking about denying the male of our species the most glorious creation to ever grace us with her presence.” I said with a smile.

“That was Rick, my now ex-boyfriend,” she replied her face getting long again. “He ran into a girl he grew up with and he said sparks just flew. He wanted to take her out over Valentine’s Day and see if there was anything there. Instead of breaking up with me, he wanted me to wait and if there was nothing there he would get back together with me. Can you believe that crap?” she continued.

I winced at the stupidity of some of my gender. I let her go and took a step back.

“So you are saying that you have a DOUBLE Cold Stone Creamery Emergency? Not feeling well AND a breakup?” I asked her.

She jumped up and down a bit and squealed again. That sound is so damn cute.

Within minutes she had a pair of boots and a winter coat on. She was pulling a knit hat on her head that had kitten ears sewn into the top and she looked so adorable. I had to give her a big hug.

“I love you so much, sis. I can’t believe how much I’ve missed you.” I said.

“I missed you too. I need my big brother!” she said as she squeezed me tight.

As we climbed into my old beater Honda, I didn’t realize how much I missed her until I saw her again. These past two years had been the first time I had been away for any length of time and I really wanted to hang out with her again. I determined to plan something just for her.

“So how many hot college chicks are you banging these days?” she asked.

Obviously there were very few topics that we steered away from. Mom and Dad insisted on open communication. Almost too much so. There was the obligatory sex talk I had with both my parents. Mom insisted on being there so she could add a female perspective to the thing. They did the same with Nat. They also let her know very early that she was adopted. Looking back I think they did it in a great way. They told her that they already had a boy and they wanted to make sure they got a sweet little girl, so they went overseas and found the perfect little addition to our family. I remember a lot of phone calls and a lot of tears until the day that they showed me a picture of a baby and said that this was my new sister and they just had to go get her. They told me it was my job to love and protect her because I was going to be her only big brother. At five years old that was a lot of responsibility but I thought it was awesome. It turns out they were thinking about having another kid when they saw a documentary on a refugee crises in the Ukraine. They started the process and after a year we had ourselves a wonderful addition to the family. At the time I thought a dog would have been a good choice also.

As we pulled into the ice cream store I thought back to our childhood. We were upper middle class and had pretty much anything we wanted. Our parents were of the limited TV and video games philosophy though so we spent a lot of time playing outside at the local park or doing whatever monthly craft my mother had committed us to. Once we got bikes, mom would let us make the three block trip to the local library. We spent many hours there reading and hanging out. As we grew older we would hang out with friends and do the usual kid things but we were still tight. Oh, she went through a phase where she bugged the shit outta me. I was 15 and she was 11 and she wanted to do everything I did. She would scream and yell and cry and whine when I would go over to my friends places. I thought she was so annoying until mom took me aside and told me she was jealous of the new friends I made in high school and she thought I would leave or ignore her. That is when our Cold Stone Creamery emergencies started. When ever she was sad or worked up I would take her to the local Cold Stone Creamery and buy her ice cream and we would talk. I caught some shit from the guys but after once or twice it died down. It helped that if I got pissed enough at them I wouldn’t invite them over to use my pool.

“Hello earth to Jake, I asked you a question,” she laughed. “How many girls are pining over Jake Johnson campus stud?”

I laughed.

“Actually none. I’ve been busy actually trying to get my work done. Besides, I got some things going on that take away from my time to socialize.” I said trying to be noncommittal.

“OOOH a mystery! I love mysteries! So what is it?” she asked.

“If it is a mystery I can’t just tell you now can I? You gotta guess.” I smiled at her.

“I’ll figure it out. But seriously how is life in the great up north?” she asked, dropping the subject.

I left our home in Royal Oak to attend college at Central Michigan University in Mt. Pleasant. It was about two and a half hours away which was perfect for me. It was close enough that I could visit but far enough away that I could be on my own. I had one more semester to go before I graduated with a BS in Electrical Engineering. I should have graduated this semester but unknown to my family, I had taken this semester off. All my schooling was paid for in scholarships so mom and dad had no clue. This was the secret I had to tell someone.

I caught up on everything that had happened since I was gone and we reminisced about life in general. We finished our ice cream and headed for home. As we drove through the old neighborhood Nat slowed her chatter and started giving me long glances.

“You look good bro, you been working out?” she asked.

“Actually I have been hitting the weights with some friends in the sports medicine program.” I replied.

“So why the information blackout this semester? Does it have something to do with your mystery?” she inquired.

I had to tell her.

“Remember when I spent those twelve weeks working for that oil company checking their rigs?” I asked.

She laughed.

“Mom and dad are still miffed with you for going to work for the oil industry.”

“Well, I noticed one of the main valves was tough to hook up and it had a history of being a weak spot in the system where oil could spray out. I figured it could be improved so I bought one off the scrap heap and brought it to Ali. He worked it up in his CAD program and we redesigned it. We hooked up with Fairy, formed a corporation, and filed a patent. Then we got busy trying to pass our classes and find work. Over Christmas break we got a couple calls from a couple different companies that wanted our design. Long story short there was a bidding war and our company made a huge amount of money. The check cleared last week and after splitting my share of the profits and paying taxes I have over a quarter million dollars in the bank!” I couldn’t contain the glee in my voice.

She gave me a dumbfounded look. She shook her head.

“You’re telling me that a bunch of early twenty something college kids are worth millions of dollars? What the hell?” she asked in amazement.

Ali al’Jazeed and Mike “Fairy” Farraday were two of my closest friends growing up. Ali was third generation Arab-American and as American as apple pie, despite his name. Fairy was a jock nerd who played football and D&D in high school. Ali got his degree early and was looking for work when he started messing with the project. Fairy was pre-law and used the formation of our company and the patent process as school credit. We decided to have our company change the world and work on making alternative energy sources profitable. We each took a lump sum and set up for most of the residuals to go back into our company. I would get my masters degree in alternative energy resources, Fairy would get into patent law, and Ali would get his masters in engineering. When we all got done with school about the same time we would have a company with capital to start our innovation.

“Why are you driving this piece of shit car then?” Nat asked.

“That money has to pay for all my expenses plus any incidentals that come up. I am not gonna go blow it on fast cars and loose women” I grinned. I didn’t tell her that I was planning on blowing at least some of it on my family.

We got back into the house and my sister immediately shed her coat and kicked off her boots. The foyer was a little cramped and as I was getting my coat off she rubbed her tight little ass right up against me. You can guess what happened.

She looked over her shoulder and gave me a saucy grin, as Little Jake made itself known.

“Is that because of me?” she asked innocently. I knew the proper response.

“It’s only because you’re so pretty.” I grinned back at her.

The summer when she was thirteen and I was sixteen she developed quickly. It seemed like she got boobs and hips almost overnight. When we would roughhouse in the pool she would rub up against me and I would get the inevitable boner. She thought that was hilarious and would tease me whenever she could. I was barely in control of my hormones so I had an erection pretty much 24/7 unless I had just beaten it into submission. I remember the conversation I had with mom when I went to complain.

“She is learning how to be a woman, Jake. She’s trying out her new powers on someone she feels safe and comfortable with. It would either be you or your father but since you are closer to her age and have a tighter bond, she’s decided it will be you.” Mom explained. “I’ll have a talk with her about her teasing but it’s actually safer for her to flirt with someone who won’t be taking advantage of her or misreading the signals. Probably the best thing you can do is acknowledge the fact that she’s attractive and reinforce her positive self image.”

The next time we were in the pool and she was trying to dunk me I popped the inevitable boner. She looked down and asked the question, “Is that because of me?”

I quickly thought of mom’s talk and gave her an answer I hoped was right.

“Only because you are so pretty.”

The smile on her face would have lit up half of Detroit. The exchange quickly became part of our regular banter.

I went to the fridge and had to grin when I saw what mom and dad had for drinks. Almond milk, orange juice, and bottled water. There was never going to be a Coke or a Mountain Dew in this household. I moved the water to the side and found a six pack of a micro brew my dad liked. I grabbed one of his beers and a bottle of water and went to sit down on the couch. I tossed the water bottle to Nat and opened up my beer. I had no sooner sit down on the couch than my sister had laid down and put her feet on my lap. She wiggled her toes inside her socks and gave me a huge grin. I performed my brotherly duties and stripped off her socks and started rubbing her feet. She laid back and I almost thought I heard her purr.

“You are going to make the best husband ever,” she said as she closed her eyes. “I want you to know that I loved you before you were rich. So what are you going to do with the money?”

“Well, mom and dad are going on a Valentine’s day cruise. I booked the best cabin available for them. That will get them out of our hair for a couple weeks. I figured I would spend some quality time with my sister and we would bum around here for a little bit then go see the Chicago production of “Hamilton”. I was planning on trying to snake you away from your boyfriend that day but now maybe we can change some stuff up unless you guys get back together.” I said as I worked on rubbing her feet.

I noticed her move as she sat up on her elbows and looked at me intently.

“Fuck him. Until you leave you are my honorary boyfriend and sugar daddy. We should spend at least a couple days in Chicago. There’s a shit ton of stuff to see there,” she replied.

She got a sheepish grin on her face.

“I’m sorry Jake, I got caught up for a sec, whatever you want to do would be awesome. I am just stoked about being able to hang with my big brother again. I didn’t mean to take over.” she said sheepishly.

“Don’t worry about it sis. The only reason I didn’t suggest longer was I thought you had a boyfriend you would want to hang with. Can you take the time off school? We could make it the whole week.” A thought hit me. “How cool would it be to take the train over there? I have never ridden a train somewhere before.”

She gave that little squeal I loved so much.

“This is going to be so awesome! I have to call Sherry!” she said as she looked for her phone.

“Nat, please don’t tell her about my money. I haven’t told mom and dad and I don’t want people to think I am different.” I said when what I really meant was that I didn’t want people hitting me up for money.

“Don’t worry Jake, she is cool.” My sister responded.

Grrr, I love my sister to death but sometimes I want to strangle her. The stupid thing is she knows that she has me wrapped around her finger. Sometimes I have to put my foot down though.

“Natalia! Do NOT tell her about my company or my money. I know she is your friend but I don’t want my business getting out there. Please.” I asked, my tone softening towards the end.

She looked sheepish and gave me the saddest pair of puppy dog eyes I have ever seen.

“Sorry Jake, you are right, I just got excited and I knew she would be also. My hunky brother is now my hunky, rich brother. She would be over here in a minute without panties begging to have your children.” she smirked.

Sherry has had a crush on me since she was 13. At first it was weird but over the years we all fell into a easy groove. She would tease me about waiting for her. The last time I saw her at our pool I was seriously tempted. I have yet to see a more perfect hourglass shape on a woman. I thought I was being circumspect in checking her out until she looked me up and down and smiled.

“Is that because of me?” she asked saucily.

Sherry was pretty cool. I knew Nat would be talking to her soon. I just wanted a chance to talk to mom and dad first.

Nat and I hung out until my parents came home, both of their hybrids making no noise as the garage door opened. I knew they saw my car parked across the street so there was no surprise as to me being home. It was still a happy family hug when they walked through the door. I mock my parents but they’re great. Mom has a degree in Psychology and runs her own real estate company. Her and dad bought a bunch of properties and turned them into rentals. The housing crisis actually made them money as people will always need a place to stay and rentals were tough to come by. Dad worked as a purchasing agent for a large building trades firm. The boss of his company was old school and carried no debt. When the recession hit, old man Montgomery actually bought out struggling competitors. Now that things were getting back on track, the future was really looking up.

My parents were thrilled when they heard my news and they were very thankful for the vacation I planned for them. I did get a talking to about sensible investing and the need for giving to charity. Dad figured I should help the soup kitchens in Mt. Pleasant and Detroit along with giving money to the ACLU. I listened intently and nodded at the right places. I was 22 years old now, I knew who I felt deserved money and who I thought didn’t.

All in all it was a great night and it drove home how much I loved my family and how lucky I was. The next few days were a flurry of activity. Mom and dad were getting ready for their cruise and Nat was getting school stuff set up so she could take a week off. My parents thought it was cute that we were going to see a show together and hang out in Chicago. I made reservations at a very swanky restaurant along with booking a suite at the Chicago Hilton. The view was supposed to be the best in the city. The train tickets were surprisingly affordable and I had arranged a car to pick us up at the station. I was having fun with this. I saved money by ordering the valentines specials when I could, that probably contributed to what happened later. Two days before we were going to leave, Nat had Sherry come over to go shopping. She swore she didn’t have good enough clothes to wear to the show and the restaurant we were going to.

“How are you paying for this sis?,” I asked.

“Mom gave me a credit card and told me not to go hog wild.” she replied.

I knew mom and dad weren’t hard up for money but I felt kinda bad having them spend money for a trip I had planned. What the hell. I had money and looking like a big shot in front of a couple of cute girls was always a good thing, even if one of them was my sister. I grabbed my wallet and fished out my credit card.

“This one has four thousand dollars and gets me miles on Delta,” I told them, “Go ahead and limit it out.”

They looked astonished but slowly grins crept over their faces. I heard twin squeals and they grabbed my hands.

“You’re going with us!” they said in unison.

I was horrified when I realized they weren’t joking. We went to the mall first then we went to a bunch of vintage clothes stores. Nat found a dress she had to have at a high end resale shop which cost 700 dollars. I was a little amazed until they told me that two years ago the dress would have been 5000 dollars. She said it fit her like a glove but she wouldn’t let me see it. Not that I was all that interested anyways. My sister would look good in pretty much anything and I was pretty sure she wasn’t going to be hooking up because she was with her brother. I was looking at this like an old fashioned play date except with real money and the ability to get some high class culture under my belt for when I took a real girl out. After she found the dress we had to go back to the mall for foundation garments. They both chuckled at my blank stare then told me they meant underwear. The day started looking up.

I am not one of those guys that gets embarrassed walking into a lingerie store. I am one of those guys that got embarrassed walking into a lingerie store with my sister. I can appreciate that my sister is a beautiful woman. I never went through and did some of the things you hear brothers doing, sniffing panties, trying to get looks into the shower, etc. She did pop up in a couple erotic dreams when I was living at home going to community college. There were a few times I would be jacking it and the thought of her would pop into my head. I always felt guilty because those few times I would blow. We had no problem talking about our sex lives, each one of us bouncing things off the other to try and figure out what the opposite sex was thinking. So with all of that being said, watching my sister prance around in new underwear was nice but not the turn on you would think. Watching SHERRY prance around in underwear was a whole other ball game. Every thing she tried on was hotter than the next. I have said before how she had an hourglass figure. My god, some of the stuff she was showing must have been a size or two too small because she was filling everything out in abundance. I was uncomfortably hard after the first five minutes. I thought we all had a lot of fun and I bought us a nice lunch. It was after we dropped Sherry off that I noticed Natalia was unusually quiet.

“What’s wrong sis?” I asked as I eased into our subdivision.

“Nothing.” she replied.

I pulled the car over and shut it off.

“That bullshit might work on mom, dad, and whoever your boyfriend is but it won’t work on me.” I declared.

She pouted at me for another second and then sighed.

“Okay, I don’t know why but it bugged me that you were checking out Sherry so much at the lingerie store. I have to tell you that I bought shit that will make your mouth water but you only had eyes for her,” she said as she looked out the window.

“Look sis, you are indeed mouth watering okay? I had to focus on Sherry because if I started ogling you too much I’d be getting totally inappropriate thoughts about my sister.”

“Mouth watering eh?” she asked with a smirk. “I like that a lot more than you ogling the considerable assets of Sherry. I’m sorry to be such a weirdo Jake. I just am all over the place emotionally right now, but seeing you has been the best thing that has happened to me in a long time. I always remember how much I love you when you come home. And a few inappropriate thoughts aren’t gonna bother me at all,” she said with a grin.

That was a little odd. She seemed in better spirits though so I let it slide. We finished the ride home in a good mood. When we got home we helped get mom and dad around for their trip. We sent them on their way and had the rest of the day to ourselves before we had to leave in the morning. I had a large suitcase and Nat had three. By the time we laid out our clothes for the next morning and got everything around we decided to order some pizza and hit the bed early. Our train left at 6:30 in the morning. Just as I was drifting off I felt my bed move and the covers slip open. I groaned at the loss of heat and then felt a form slide up next to me and give me a tight hug.

“I need my cuddle buddy tonight,” was all she said as I positioned myself to wrap an arm around her. I guess this was another oddity with us. When she was about five years old she started ending up in my bed. I was a sound sleeper so I wouldn’t notice until we woke up in the morning. Despite repeated attempts to keep her in her room she would always seem to end up cuddled into me. Since it happened shortly after she was told she was adopted, mom figured it was a coping mechanism that was largely subconscious. She worked with my sister until it stopped but by that time I had gotten used to having her cuddled up in bed. I never told anyone how much I missed it. Since then if she was having a rough time I would find her in my bed when I woke up in the morning.

I woke up early with a faceful of hair, a morning woody smashed between my sisters panty clad ass and my abdomen and a handful of soft mammary excellence encased in a thin cotton tee shirt. I went to get into a more appropriate position for cuddling with my sister when I heard her growl.

“Keep that hand there or you are gonna lose it, mister.” she said, sleepily.

I got even harder. My tired head to rationalize it away. After all a morning erection is pretty much involuntary and I was asleep so I didn’t really know that it was my sister’s tit I was grabbing. What I wasn’t sure is why I wasn’t letting it go. She seemed to want my hand there and I admit she felt wonderful. I decided to to not worry about it and kissed her neck gently while cuddling in a little closer. I’m sure if I’d been wide awake I would have reacted differently. As it was I fell back asleep while enjoying the intimacy.

Twenty minutes later the alarm went off and we disengaged. We rolled out of bed and she gave me a sleepy smile and yawn. Her tee shirt rose up a bit when she stretched giving a nice view of her toned abs. She came up to me and gave me a big hug.

“Thank you for letting me cuddle and not freaking out,” she said. “I needed that.”

“I will never turn away the prettiest girl I know when she wants to climb into bed with me,” I replied with a smile.

She gave me a huge grin and kissed my cheek. Then she sauntered off to the bathroom. I shook my head and started out planning my day before I realized that I had basically groped my sister during the night. She didn’t seem very upset about it and frankly I was more worried that I was okay with it. I guess I chalked it up to us just being close and having a little different bond. I started getting my stuff around including my new suit. I heard the shower turn off and it moments later a pale goddess emerged surrounded by steam and clad in a towel that covered her tits and hung down to just below her ass. She had a towel wrapped around her hair and she looked clean and pure. I realized how much I really loved my little sister. This was the first inkling I had that things were going to change.

I sat watching the light snowfall on the fields of southern Michigan through the train window. It had been wickedly freezing as we rushed to board the train but now that we were underway it was peaceful. Nat was cuddled up to me dozing. She had the ability to fall asleep anywhere especially when we started moving. An older couple that was walking by stopped and looked at us fondly.

“You guys are just too cute!” The older woman gushed. “It is so nice to see two young people in love.”

Her husband snorted and gave me a sympathetic look.

“Sorry”, he said “This is our 40th anniversary and she is all starry eyed. Now Martha, leave these two young lovebirds alone.”

The lady swatted her husband on the arm.

“George, be nice and maybe I will cuddle you like that later tonight.” she said with a saucy grin.

He just chuckled and gave me wink.

“Who could pass up an invitation like that?” he asked me.

He kissed the top of her forehead and they walked away after wishing us well.

I felt Nat reposition herself against me. I looked down at her and she was staring up to me with those beautiful grey eyes.

“Can we be lovebirds this week?” she asked.

“What?” I replied

“Can we pretend that we aren’t a brother and sister, instead we are a couple who is taking their first out of town trip together to see how compatible they are. You are a mechanical engineer for Ford and I just got a job in accounting. We met six months ago when I had to have you explain some charges on your department invoices. We hit it off and this is the next phase of our relationship,” her eyes were sparkling as she got into the little tale she was weaving.

“It’ll be so much fun, you won’t have to introduce me as your sister and get those weird looks. Instead we will just be another couple checking out the streets of Chicago on Valentines day,” she continued.

It was then that I remembered it was Valentine’s Day tomorrow. Mom and Dad had always thought it was just a commercial holiday designed to sell Hallmark cards so we never got all that into it. Although Dad always made sure he brought home flowers for Mom sometime that week. He wasn’t a dummy.

I could tell she was gonna have fun with this. What the hell, why not? No one knew us in Chicago and if my sis wanted to have some fun who was I to say no? What was the worst that could happen?

We took a cab from the train station to the hotel. Check in was a breeze, it should have been considering what I paid for the rooms. They had been running a Valentine’s day special which gave me ten percent off so I gladly took it. The room had an awesome view of the Chicago skyline that you could admire from the bed or the hot tub.

I dropped my bags and took in the view out the windows as Nat rushed into the bathroom to pee. I swear she has a bladder the size of a walnut. It suddenly dawned on me that the Valentines day suite would only have one bed. I chuckled to myself and thought that this is why I should let others do the planning.