My Petite Fiancée Surprises Me

Warning -- This story may contain irresponsible sexual behavior, some light cuckolding, some light domination, both gmo and non gmo foods, gluten and cold drinks without coasters. If any of these things offend you, please move on there are plenty of great writers on this site, please don't waste your time getting angry, angry comments bum me out but I LOVE when people say my stories excite them or constructively suggest possible improvements.

If you haven't read my other posts -- I'm not comfortable around people and very shy around women. I live with my 5'1, guessing 95lb, gorgeous blond girlfriend (Heather). Her petite, athletic, guessing 100lb, 19-year-old bombshell sister (Tammi) has been staying with us. I've been putting off the proposal to my girlfriend because I want to wait until I've saved enough money to pay for it.

Heather was so conservative when I met her, and I love that about her but now she's a little bit naughty and I love that too. She'd tease me (when her sister Tammi first moved in) as she'd spit polish my jungle boot which was conditioning me to think about sex when I see Tammi.

One thing led to another, and my girlfriend actually gets off, watching me have sex with her sister. I'm not shy free yet -- I don't look forward to parties but I'm a lot less uptight about sex so I've made a lot of progress on my condition.

End Recap

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About eight months after the first time that I made love with Heather's sister, Tammi came home on a Saturday afternoon. She hadn't popped into the living room yet so Heather and I figured she was making herself a late lunch or a snack. Heather and I had already done all our chores for the day so we just chilling naked on the couch, just channel surfing. She had her head on my lap as I brushed her hair. Eventually when we didn't hear anything Heather nudged me to check on her sister.

I tried not to feel shy as I walked out into the kitchen without my briefs and tried to act casual. Tammi was standing in front of the sink, looking out the window. "Hi Tammi!" I said. "How was your day?"

Tammi came over to me an embraced me tightly. "It was an interesting day, today," she said. "Something possibly good or terrible happened but I'm not ready to talk about it yet." She pulled me down and kissed my lips and then adjusted my arms, so I was holding her closer, then nodded her head in satisfaction. I get a kick out of it when she helps me do the right thing.

"I needed this so badly, I need to feel you close." I helped free her of her horribly restrictive clothing she wears when we are in public. She looked at me and smiled as she always seems to appreciate the help.

I lead her back to the couch and instead of sitting next to me and her sister she immediately straddled me even though we had sex in the morning. She usually gets a bit tender, so I try not to wear her out. (I'm not huge or anything, I'm a little over seven inches but I'm told I'm much wider than some and the girls are only about five feet tall and have wonderfully petite lady parts). She just said, "I need you to make love to me, Daddy!"

I still haven't asked why she started calling me Daddy. I think part of it is she likes making me blush and that does make me blush, but I think the other part is that even though I'm just a couple of years older than her, she thinks of me as old fashioned. Or perhaps it is because I can't help but be very old fashioned in a lot of things as I think they are the better.

I didn't want her to ever feel like there is something I wouldn't do for her, so I immediately reached down and pushed the head of my cock into her wet little pussy. We kissed intensely as I let her ease it in until she was comfortable. I pulled on her firm little buns. OK, I didn't just pull on them, I grabbed them, I squeezed them, I enjoyed their give, as I gripped them hard.

I rubbed my hands along the smooth soft skin of her tone legs. Her kisses never let up in intensity, I think she wanted to see if she could lick my tonsils. She was going to have to try hard as they were removed when I was a child.

I reached up and felt her sister Heather's hand stroking Tammi's back as I made love to her little sister. It was interesting feeling another hand on her back as I stroked it while gripping her right bun for leverage. Heather's hands are so soft and gentle, Tammi is a lucky girl. Tammi pulled back from my mouth. I noticed tears were coming from her beautiful big blue eyes. I figured she WAS tender, and she was not to make a big deal of it so I tried lifting her up. She surprised me when she slammed back down.

"Harder, Daddy!" she yelled. I didn't want to hurt her, but I wanted her to enjoy herself, so I slammed hard into her hot, wet, little pussy. "That's it, Daddy, harder!" She'd never asked me to go harder but I'm happy to try new things. I started pounding into her vehemently. She slammed herself onto my cock enthusiastically. I tried and I tried but couldn't hold on, I was almost ready to blow my load.

"I'm about to cum baby! Can you cum for Daddy?" I asked.

"Yes, Daddy, just a...Oh Daddy, I'm doing it can you feel it?" She asked.

She was squirting on my cock; I love it when she does that. I'll be honest, I was about to blow if she did or not; my cock makes all the calls in my relationship with it.

"Oh, good girl, I'm cumming inside you, Baby... so hard. Who's your Daddy, Baby?!" It was a gusher; I was flooding her little young pussy with my plundering soldiers.

"Daddy, I feel it! I feel it! Ooh yes, your swimmers are finally in my pool!" she said.

She then snuggled under my chin, and I could feel her tears dripping on my chest. I felt like I should do something, so I tried to rock her a bit as I rubbed her back and she eventually fell asleep. I looked over at Heather as if to say, "what was that all about?" and she seemed to understand.

Heather kissed my forehead and then gave me a gentle but wonderfully tender kiss on the lips and she said, "I'm so proud of you!" I'd cum a lot over the past couple of years but it's always nice to be complimented on it even if you aren't quite sure why. I think most girlfriends would get upset about their boyfriend shoving their cock in their little sister, let alone the cum stains on the couch. Heather's the best!

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It turns out, Tammi got offered a great position at the blood center but in a branch that was nearly 200 miles away. Talk about bad timing, with the money Heather was making with an established client base at an exotic car dealership and I were making in IT (my boss took a job at a startup - so I was given his job on a trial basis -- I even had a new hire reporting to me!) we could afford a bigger apartment or even a down payment on our first house!

Tammi was finally debt free and had started to chip in a small fraction for rent which we used for luxuries like some nice meals, new linens, scotch guard., etc. She did so much work around the apartment we didn't feel right accepting too much for rent.

Tammi wasn't sure about the job, but Heather and I told her if she didn't like it, she was always welcome back home, but she'd probably regret it if she didn't give it a chance. Neither Heather nor I wanted Tammi to go but we felt we might have forced her into her current path without having any say of her own.

The position stayed open for over three months until they upped the salary and Tammi felt she could live on those wages. She moved out in late May not that long after Heather's birthday. (Tammi encouraged me to spank Heather's naked bottom for each year of her sister's life. Turns out my girlfriend insisted she wanted that every year for her birthday from that year on!).

It took a while to get used to having her sister gone but Heather and I somehow became very connected in a new way -- we could just smile and the other would know what we meant. We'd still say I bet Tammi would like this show but her moving out gave us more time to spend on our relationship and it was an adventure. I think Heather felt bad for me as I was down to 'just her' as she put it. I told her honestly that I loved her and really, really enjoyed sex with her.

We'd go for more walks together. We got to spend more time when we made love on the weekends. We could talk about anything or not talk at all, and it could be electrifying. When Heather put her little hand in mine, I still felt something like shyness, but it is a sensation I treasure.

She got upset with me because I tried to get takeout more often since Tammi wasn't there to make us meals. Heather got offended thinking I didn't like her cooking any more. I assured her, that her meals made with love were better than anyone could ask for, so once a week when she'd have a long day, she'd pick it up, so it was at least served with love.

I know Heather missed her sister and best friend a great deal, but they'd talk almost every couple of days. Sometimes we'd watch TV shows together over the phone. I was told never to tell Tammi, but Heather usually had bittersweet tears at least once a week when the phone calls were over. She can be a bit of a mother hen worrying about her baby sister.

For me it was very hard to say what I missed most. I really missed my jogging partner, but I think part of that was watching that tiny thing eat, when we finished. She was an unstoppable machine! Or perhaps I miss the way she'd steal my food, taking great delight in being bad but then feeding me all her food and drink. I miss her just plopping down in my lap when I was on the couch. I miss her happily skipping around the apartment naked.

All that being said, I think deep down both of us hoped she'd eventually find work near us again as a weekend or two a month wasn't the same. We'd get together every few weekends, but Tammi and Heather would be in tears every time we said goodbye. I might have gotten emotional too if it weren't for the pollen making my eyes get watery.

We figured we'd finally take that trip to Hawaii and see if Tammi could join us (Heather won an absurdly expensive vacation package at work a while back). Heather bought a ticket for Tammi that night, we'd meet up at the airport in Oahu. We booked for mid-November -- I guess not exactly a busy time for them. It was my first time flying with Heather (also my first time in first class!). We got to hold hands the entire flight until she fell asleep on my shoulder. She looked so cute, like she felt guilty of something when she woke up.

We met Tammi at her gate about an hour after our flight landed. She immediately made a bad joke about us already getting lei'd. Curse her! She beat me to it. We called the hotel and they arranged for a shuttle that picked us up in about fifteen minutes! Which gave us plenty of time for her luggage. You'd think that since the girls were so petite and we were on a very warm island they wouldn't have much to pack but somehow each had twice as much as me.

The hotel was very nice (far, far, FAR nicer than any I'd been in even for business) and it had an ocean view. Everyone we met from the woman at the gate to the nice gentleman that drove us to the hotel had a mellow and super friendly way about them. I don't know why but I expected everyone who lived in Hawaii to be that way.

I was surprised when the desk clerk was about a 55-year-old woman from somewhere in Southern US -- perhaps, Alabama. She had this business only attitude like and uptight school principal or librarian or an HR person that writes up people for open toed shoes.

The hotel was probably at about 20% capacity, so they tried to upsell things. For $200 more a night we upgraded from the lavish deluxe suites which was one of their best to one of their honeymoon suites. The honeymoon suites included a hot tub! For another $75, they'd restock the honor bar "for free". We don't drink a lot but what they hey why not, I'm sure a can of nuts was $10 (turns out they were $20!).

The woman at the counter gave me an odd look when I carried the luggage for my girls. She said all guests were an extra $150 per night and asked if we wanted a spare bed sent up. Tammi needed to make me blush and said to her, "Why on earth would we want that?" then she pinched my butt hard enough to make me jump and yelp! Heather started snickering and started rubbing my chest while winking at the humorless woman.

I gladly paid the fee with a burning red face as the woman stared as I could feel her judgement. I don't know if it was the situation or a slow internet connection, but it seemed like a lifetime to get the extra charges approved. We finally headed up to the room.

The girls were laughing and acting like school children the entire elevator ride. Heather found a laundry bag and that was included in our suite package, so we put our nasty airplane clothes in the bag for cleaning. It was nice to see the girls naked. I couldn't help it, but I think Heather was actually shy I was ogling her even though I do that every in our apartment. It was great to see Tammi excitedly skipping around the suite as she explored it.

We went to the bathroom, and it was bigger than our bedroom! It had a big, big tub and a HUGE dedicated shower. It was more than twice the size our shower at home and had a shower head on both sides. Heather smiled at me, and we both made a mental note the dual shower was going into the house we'd build. There was a raised jacuzzi right next to the balcony in the living room so you could look out and see the ocean. (I'd never stayed in a hotel where there were more dedicated rooms than the bedroom and the bathroom)

I only paid for the upgrades but I'm guessing this place was at least two to five or more grand a night during peak season! I didn't know and honestly was afraid to look now. I'd never ever, ever, ever considered a hotel like this, so I really had no idea. I stayed in an embassy suite once and that was a big upgrade for me over the ones I stayed in when my family went on vacation.

We figured we'd get that dirty airplane feeling off ourselves before we went out. I didn't plan it or anything, but one thing led to another, and I ended up taking Tammi from behind in the shower while Heather gently soaped Tammi's back. I could tell Heather missed taking care of her little sister as much as I did. It was so nice we'd get to spend some quality time together for the next week! That shower relaxed me so much it was worth the several hour flight.

I wanted a nap after the shower, but the girls got me dressed and down to dining area. It was a fancy restaurant, and all meals were included. We tried a local fish platter; it was very fresh and tasted great (what a treat). We then explored the main shopping street. The girls wanted a bathing suit as a souvenir of the visit.

I suffered as the girls made me watch them try on little bikini after bikini. They asked me to pick one for them but for some reason they thought what I liked was "obscene". They decided on some revealing but 'reasonable' bikinis that they looked amazing in, so we were all happy. They also picked up a big bottle of sunblock 50. The sun wasn't very high anymore so we wouldn't need much until tomorrow.

We wandered over to the beach area again and it was really something. I expected to see lots of boats, but I only saw four and two were sitting on the beach. I was expecting to see thousands of people, but I'd be surprised if there were even a couple hundred on the miles of beach we walked, maybe they were more crowded early morning.

The next day, a guy on a small catamaran convinced us to go sailing for $75. I'm betting we got a great price so he could look at the girls. It was amazing, we saw turtles come right up to the boat when the wind wasn't blowing.

The girls yelped when we were moving at a good clip but seemed to really like dangling their legs off the trampoline. With their little legs they could catch the spray from the ocean, even though they couldn't reach the water. We walked almost the entire length of the beach and back afterwards. We were super diligent about the suntan lotion; I applied it to every bit of their bodies every hour. The next day we hiked up Diamond Head.

I don't think I've ever been more relaxed. I admit it was wonderful having real sex twice a day again! Tammi also gave me blowjobs and Heather gave me hand jobs as she told me new and filthy stories about Tammi while Tammi helped! Tammi added some filthy little plot twists! I couldn't last long when they teamed up. It's impossible not to look at their wonderful, warm, caring, angelic faces and not want to cum all over them. I'm not sure what it is about the island air, but I was freakishly horny the entire trip.

We took a tour the following day. The bus driver was a huge Samoan dude that cracked us up the entire way. He pointed out every restaurant we passed or should go to. He got most excited about the points on the tour that had food, like the ice cream stop. He made me want to live on that island -- I have no doubt we'd become eating buddies, but I'd have to jog twice as far and he'd still out eat me (I can eat A LOT) but he seemed to make every meal sound like heaven.

We rented some equipment and went snorkeling on the next day. By the end of that day we all had a nice tan. We still looked absurdly pale compared to the locals but when we got back to the rooms the girls had serious tan marks. The girls seemed upset by them, but I just considered them like traffic maps pointing out areas of special interest. I tried to point out they should have gotten the much smaller bikinis I picked out for them but apparently that wasn't being helpful.

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That evening we celebrated Tammi's birthday. I made extremely strong screwdrivers from the honor bar. Tammi was already on her second. I had just finished my second but I'm nearly twice her size. We weren't sure what to get her, so we (Heather) got her a flower of the month card, so she'd know we were thinking of her when she went back.

I got her a big gift certificate, but Heather told me that I could give that any time and it was too impersonal for her birthday, so I mailed it to her when we got back. (I put it in a folded sheet of paper with a picture of my cock standing up with a note on it that said, 'thinking of you'.

She called me about it right away to tell me she got a big laugh and how much she appreciates it and the gift certificate.) We laughed and chatted for about 30 minutes before her sister ripped the phone from my hand and blabbed for two hours straight. I'm kidding, I love how close they are and how much they enjoy hanging out. I'm guessing I would not be that close with a sibling.

That night after we had showered, Tammi said she was hoping I'd give her something special for her birthday. She said, "Heather already said 'you have to do whatever I say', so you really don't have any choice." I assumed she was moving to a new apartment, so I had no problem driving out there and lending a hand. She really owned very little. I had more junk when I was in my dorm in college. She then went skipping to the bathroom and back again with a tube of something. I figured she was going to put lotion on my elbows while she tried to soften the request.

She grabbed me by my cock and took me to the balcony. I was a little shy, but we were 10 stories up, it was dark, and the island wasn't exactly bustling. Just her holding onto my cock made it swell. She then got down and put my cock in her mouth. I missed our time together!

My cock was now standing straight up. She stood up and applied some goo from the tube to my cock. She whispered in my ear, "I want you to take my cherry on this balcony!" She wasn't even a virgin when we met so I guess this was a role-playing game and I figure why not. I was all set to be a bad cop or a cat burglar. Tammi bent over the balcony rail, then turned around and grabbed me by the cock and aimed it at her rosebud. Ohhh -- that's what she meant! I'd never tried it with anyone, so I was nervous.