My Petite Fiancée Surprises Me Pt. 08

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Put your money where your mouth is.
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Part 8 of the 11 part series

Updated 11/29/2023
Created 10/14/2023
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Warning -- This is a story about the love of my life and my terminal shyness, so it progresses very slowly.

If you haven't read the other stories -- I'm not comfortable around people and very shy around women. I live with my 5'1 gorgeous blond girlfriend (Heather). Her petite, athletic, 19-year-old bombshell sister (Tammi) has been staying with us since she graduated with a 2-year degree. I'm trying to save every penny so I can afford to ask my girlfriend to marry me.

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 keeps been teasing me (for the last couple of months) with naughty images of her little sister while she strangles my dangle which is conditioning me to think about sex when I see Tammi. She finally just admitted she did this to see if I'd cheat but she's still trying to convince me to do it as the idea excites her.

End Recap

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The day was perfect! It was low 70's sunny and dry. Fall was over a month away, but it almost felt that good -- my favorite season of the year. I was in a pretty darn good mood. OK - maybe I was still smirking about this morning's rodeo session.

Heather and I had another conversation about getting married.

"I told you a couple of weeks ago I want to propose to you," Heather stated. "I confessed why I hadn't yet... Did you ever think about proposing to me?"

I wasn't sure if her sister Tammi had blabbed what I told her or if Heather was fishing. While Tammi and I were showering, I admitted that I was working up the nerve to propose to my girlfriend. I figured I'd see where this goes -- it could be fun. "I considered it, but I'd need to save up lots of money first."

"It's not like you don't make good money and if I paid for half, we could do it sooner. I'm sure my parents would be happy to pay for the whole thing (they are quite well off)." She said possibly hinting I could propose as soon as I was ready. I try not to be too set in my ways but I'm kind of old fashioned and was told men do the proposing but only when they can afford to take care of a woman.

"A nice small wedding alone would set us back $6K for the ring, $30K for the actual wedding, a good lawyer for the prenup is $10K, the honeymoon will be at least $6K and I figure another $5K for incidentals," I said. If all went well, I'd have saved enough to marry her in about 2 years.

"WOW, my honey has really been researching this stuff." She said as she pulled me close for a smooshy kiss on the cheek. "I don't need a fancy ring and we could just have immediate family. I hadn't really thought about a prenup, but do you really think it costs that much?" I don't even think we need one.

"Let's be realistic," I said trying to sound stuffy and serious. "I don't think anyone gets married thinking they'll ever be that person that gets a divorce. I don't want to be one of those couples that argues about every penny making the divorce turn them to enemies. Even if one person manages to get out happy that is a gift. I want the best of the best so we both aren't bitter," I said.

I think she was a little thrown off by my statement. "You almost sound like you plan on getting a divorce. I don't mean to offend you, but you realize I'll probably make more than you in just a few years and my parents are, for a lack of a better term -- loaded."

I turned to her, looked her in the eyes, kissed her hand and said, "That's exactly why I'd pay for the best of the best! I'll want a big piece of that pie and I'll never be able to wear white again at my next wedding!" She smiled while punching me pretty hard in the arm. I hate having serious discussions but sometimes she's a sport and brings it right to the net for me. She's impossibly cute when she pretends to be upset.

Heather and I talked about moving to a house or a nicer apartment as she could tell the wedding conversation wasn't going to go any further today. We had finished off paying our student loans and Heather insisted she would pay for half of the utilities, groceries, and rent. I didn't like that idea, but she had a right to feel she had a say since she made about the same as I did currently. Heather and I had enjoyed a lovely long leisurely walk and spent time relaxing in front of the pond. We just got home when I mentioned I was getting hungry.

Heather said, "let me see if Tammi is joining us and I'll be right there." She went and knocked on Tammi's door -- the music was on a little louder than usual. I hope she didn't feel abandoned by us.

I heard some mumbling but didn't quite understand what they were saying to each other when I heard Tammi say pretty forcefully, " ... He's taking me out for dinner before the movie! Just let me find an outfit! I don't have a thing to wear. I haven't even showered yet and I need to get ready!" I know she wasn't angry at Heather, but she sounded intense. I have no idea what the rush was -- she was home all day as far as I knew.

Heather came back and said, "she's got the jitters because of the first date. She'll be fine. My girlfriend then made pork chops, spinach, mash potatoes that couldn't be beat while I helped set the table including candles. I pulled the curtains as it was still light out.

We barely spoke but just looked at each other lovingly throughout the meal. She held my hand throughout the meal which gave me the chills (in a good way). It also made me eat like a human instead of the cookie monster. I think we were too busy enjoying the other person's smile to waste the moment with conversation. If I didn't know better, I think she was a little shy when she saw the way I looked at her.

Heather pulled her chair close to mine and hand fed me a little apple pie she picked up in the bakery. When she takes care of me, I get very shy, and it is like a continuous jolt of electricity -- but in such a way you don't want it to end. I get concerned about the level of attention I'm getting but I enjoy it intensely, even though I shy away from it much of the time. I don't think I'll ever stop being shy in this way and I really don't want to stop.

I helped with the dishes until Heather bumped me with her tiny tush and said, "Scoot -- we've got the whole evening -- see what's on TV tonight, we could binge watch or maybe watch a movie for a change." I liked that, we deserved a movie -- something old or something new it didn't matter, just being close was all that mattered.

I sat in front of the TV, studying the guide to see if anything good was on tonight, 98% was garbage or just not that romantic or fun. I heard Tammi in the kitchen talking to Heather. I didn't hear her walk by, those two need bells -- they are so light they don't make much noise when they sneak through the apartment. I turned down the TV and heard, "I'm so sorry, I shouldn't have been so huffy before, I was nervous and took it out on you. You know I love you don't you." I could then hear some back patting. I don't think I've ever seen a fight between those two last a half a day.

Tammi then popped in front of the living room doorway, "Well?" She twirled slowly in front of me. Apparently, she was concerned about her outfit. She was wearing little white sneakers, a pair of tattered jeans, white blouse, some sort of bra and a light jacket.

"Well, what are you thinking?" Tammi was trying to pull a response. I think I like it much better when she runs around half naked. I think I like looking at her sexy little body. What the HELL is wrong with me!? I swear sometimes I think because my girlfriend says such naughty things about her, while jerking me off, it makes me think things I really shouldn't about this very sweet and innocent girl. Thank goodness she has no idea! She asked me something...oh, yeah...

I managed to get out, "very nice," without all the other words that came to mind.

Just then we heard what sounded like what my friends would call a "rice burner", and some old Twisted Sister? or Quiet Riot? blared. Sometimes I hate living in an apartment complex. Then there were three long beeps and Tammi said, "My date is here!" and she dashed out the door. Her dates a charmer I thought.

I decided to look at the door so I could identify the car in case he tried anything, and I needed to push it off the road. It was a blue civic with lots of chrome and an air spoiler, because if any car needs an air spoiler, a Honda does. I have no idea why, I hadn't even met this fellow, but I wanted to punch him in the throat. I'm not usually violent but I keep in good shape so I'd never back down from a fight if I thought the cause was just.

Heather came out of the bathroom saying, "did you hear our neighbor?"

I said, "that's your sister's date," I said doing my best to conceal my opinion. I can't judge, she's got her own life, and I shouldn't assume anything about him because of his defiled car or deafening music or lack of manners.

"Oh," Heather said. There was a long pause before she said, "come with me." She was standing in front of the bathroom. There wasn't that far that we could go in our little apartment. I came to the bathroom door and there were a bunch of lit candles. The bathtub was filling with bubbling water.

Heather is tiny, so when she's alone, the tub is just right, but I'm 6' and have a decent amount of muscle mass so I can't do much more than put my legs flat and have the other half of my body sitting upright. Our tub is absurdly narrow -- I didn't notice it was unusually so until I'd already moved in to the apartment. I appreciated the attempt at romance although, but the apartment's tub was too short for an adult male.

Heather sat in my lap and I gently caressed her with the washcloth all over her delicate skin. We tried to make it romantic, but she was too cold as she didn't even have as much water sitting on me than I did. A little over a week ago when it was unpleasantly hot this would have been fine.

We got a good laugh though and warmed up in the shower. We just pampered each other and smiled, enjoying the moment. It was an odd day as we said so little to each other, but it was an intensely intimate day. We kissed like teenagers for quite some time before I shut off the hot water. Splurging was fine now and then, but I'm not made of money!

We toweled each other off until we were dry, and Heather did the unexpected, she went to the closet for a light blanket and said, "You know we've probably got 3 hours more before she gets home," she said with a naughty and yet angelic smile. I felt like I was getting away with something in my own apartment as I joined her on the couch. We got under the blanket completely naked on the couch. We ended up watching something that I didn't expect to find romantic -- This Old House.

We let our imaginations' run wild as we discussed features we'd have in a house we couldn't afford. I made sure we put in a "4-person tub" as I wanted both of us to have plenty of room in the tub. I figured if that wash basin we had was a 1 person tub, it would require a 4 person tub to fit two adults comfortably.

Heather grabbed my cock gently and said, "Oh, if we had a tub that big, we could be in there right now! Would my honey like that?" I'm pretty sure she was talking to me but sometimes it was hard to tell if she was having a conversation with my friend under the blanket. She turned to me, and we kissed deeply. We went at it for a good long time when I could swear, I heard the front door open but it might have been something on TV. I hadn't heard the noisy car whining or heavy metal music blasting so maybe I just imagined the sound in the kitchen. Heather looked at me like she heard it too.

Tammi walked into the living room and started talking. I guess date night was over for all of us. "He seemed like such a nice guy at first. We went to Waffle House and had a meal. Then he tells me he'll be right back, and I see him go out the door. While the date wasn't great, I was thinking he was going to ditch me right there! Then I see him go around to the side and talk to these guys that looked like trouble. They handed him something and he comes back and says, 'I've got a treat for you.'

I'm curious what he had in mind but then I saw him put some pills from a bag into his mouth and then swallow some soda. He says 'give me a kiss' and he's got some pill on his tongue. As if, I have no idea what he took or what he was trying to give me. I just walked to the bathroom and locked the door and ordered an uber. He had left by the time my car arrived. That Prius is so quiet compared to his Honda."

"So, what are you guys watching?" Tammi asked as she plopped herself on the couch next to me. I didn't say anything, but I could feel the rivet from her jeans touching my naked hip. We hadn't had the opportunity to get any clothes so we just hid there probably both thinking we could dart to the bedroom when Tammi goes to get changed. We were very lucky she didn't just try to sit in my lap like she usually does.

"Umm this old house," I finally managed to say. "Why don't you get ready for bed and join us for a movie?" I said thinking she'd much rather a movie than watch this TV show.

"That sounds soo good," she said. "When I get back, can I crawl under the covers with you guys?"

"Sure, why not," I figured anything to get her out for just a minute. Tammi did the unexpected though and put her hand under the blanket to hug me as she said, "you guys are the best!" Her soft hands were very cool to my chest and shoulder. As she lifted the blanket to tuck me back in, she saw I wasn't wearing anything. I figured well, I guess she knows what her sister and I were enjoying on our date night. Instead, Tammi said, "Perfect, that looks so comfy, thanks for inviting me!"

I didn't know the words to say, and Heather wasn't of any help. My girlfriend reveled in my embarrassment though. Tammi stood up and started taking off her clothes right there. Heather surprised me and grabbed my cock and slowly worked her little hand from the base to the top. She whispered in my ear in a sexy, sexy voice, "I'm going to keep teasing him until you cum and there is nothing you can do about it." Then she whispered, "you like watching her get naked for you, don't you?"

I nodded without thinking.

Tammi folded her clothes into a tidy stack as she removed each article until she had just a pair of skimpy undies on. She looked so much better like this. My cock was swollen and hard and completely under my girlfriend's spell.

Heather whispered in my ear, "Tell my sister to take off her underwear but be nice about it!"

"Tammi," I said clearing my throat as Heather stroked me. "You should take off your panties, you look so much prettier when you are completely naked." What the hell did I just say?

Tammi slipped off her tiny panties. "You are so good for my ego!" she said. She was now completely nude, as she should always be. I could feel my cock continue aching. She looked out of place with so much clothing on before. I was completely used to her wearing next to nothing or frankly nothing at all when we are home alone. Tammi climbed under the blanket next to me. Her body was cool but she snuggled in tightly under my right arm to warm up as she made little sounds of contentment and comfort.

Heather continued to gently flog my log even though Tammi was right there. Heather decided to take my embarrassment further and pulled the covers down so my cock was in plain view as she stroked it ever so slowly.

Tammi sounded giddy. "Oh my, I've been dying to see this. Do you have any idea how much my sister goes on about how much semen you can unload? I know it has to be an exaggeration but I'm so excited you are including me! I didn't believe her about how big you were, but this has got to be just her telling tales!" What the hell did Heather say and how much do they tell each other? I've said it before, I'm not abnormally large, its just that they are so petite, it makes me look impressive.

Heather said, "Oh yeah, I'm so confident, I'll bet you $1500 off the car loan that I gave you that it is true." Hey, I'd like to know if it is true myself. What's true? I'm pretty sure I was what this discussion was about, but I didn't want to seem self-centered. I finally managed to whisper to Heather -- "what are you betting and why?"

"Relax," she said. It is a no-lose situation. I wanted to give some of the money I loaned to her, back since she does most of the housework these days. She's like a live-in maid who gives me ammo to embarrass you! I loved the way she took care of her sister, but I didn't understand the bet. Heather continued, "you know how my tiny sister can swallow an entire 16-ounce beer in one chug? Well, I told her you cum so much that not even she could swallow it all!"

Wait, what? Did she bet her sister that she couldn't swallow all my cum? Was I supposed to fill a cup or something? Was this finally crossing a line? This was very embarrassing. God damn, Heather's hand was working me up, I can't believe Tammi is watching me like this. I can't believe I'm looking at Tammi's naked body as my girlfriend tries to get me to cum. It seems so wrong. I'm enjoying this way too much.

Heather said, "There's plenty of room if you want to help," to her sister. Tammi looked like a kid on Christmas morning. She went to grab hold of my cock but then said, "Wait, what if I lose?"

Heather just said matter-of-factly, "Don't be so pessimistic, If you take the bet, I may take $1500 off what you owe me, but you may have to swallow his cum anywhere at and any time I say for the next whole week. Remember, I told you not only how much he cums in a session, so back out now if you are chicken!"

"You are so on, Sis!" Tammi said defiantly.

I finally spoke up "Don't I have any say in this?" Heather looked at me lovingly as she stroked my cock, she slid her fingers around the top, touching gently every bit of my helmet's rim. I could hear my precum oozing through her fingers as she rubbed my cock. What was I going to say? "Umm, well, I should get to say where and when too!" What did I just say? That was useless, that doesn't help poor Tammi out in any way. I had to think of a way out for Tammi as I doubt drinking cum is like chugging a beer.

Heather said, "OK but to change the bet, you must put up $1500 from her debt to you as well. I nodded my head in agreement. Money was tight but fair is fair, and Tammi works hard to make our home a home.

Heather threw in, "Tammi, since he's in on the bet, you get $3000 off your car loan and you agree to getting filled with his cum any time, any place either of us say for a month. Oh, to make it fair, he can't jerk off any time during the month or we have to start the date of your duties back to the start. "If anyone wants to change the agreement you have two minutes to request a change. I knew I could come up with something in a minute; definitely in two, I'm a pretty smart guy.

I felt Tammi's hand join in on my cock. I looked over at her and she looked quite happy. I know I was. It looked like a scene from a porn movie only my actresses looked way hotter. They were working my cock deftly, like this was something they'd been doing for me for ages. It felt amazing and looked so decadent. Hold on, I need to think of a way to save Tammi from me! Heather kissed my neck; her lips were parted, and her tongue was touching my neck.

Heather crawled up to so her mouth was next to my ear and whispered quietly but seductively. "My poor honey can't think, can he?" she giggled and said, your trying to figure a way out of this. Quick honey, what's 9x9?" Ha, I got in the top 96% for math on my SATs. She gently bit onto my earlobe. I know that one. 8x8 is 56, I meant to say 64 it is definitely 64, so 9x9 is 72, yeah, wait, why does that seem off, 64+9 is -- no that's not it. Oh god, I could feel more precum oozing from my cock, I wasn't going to last long now.

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