Annie: Valentine Mine

Barb fucking me was like at the party, where she had a long, loud build up to a massive cum while Becca was getting turned into a ragdoll. This time, though, I made sure not to come in Barb's beckoning pussy. It took some concentration, but I managed to control it.

When Barb moved up to getting eaten and Abby started fucking me, I had a moment of panic. Abby just felt so damned good, it was very difficult not to lose it in her. Before, she was fucking me after I'd spent in Barb, so I didn't have as much of a problem keeping it throttled back. This time, I had to concentrate. Fucking Abby, with her long, slow, cushy, sensuous rocking reinforced my desire to connect with her more often.

Kudos to me, I managed to fuck all four of them and not cum. I managed to stay hard, do well with the oral and manual, and leave all four sated. When Abby and Barb finally decided they were done, I breathed a huge sigh of relief. I was really hoping Annie would like the video and not go all Green-Eyed Monster on me. That's when Jill threw in the monkey wrench.

"Okay, so Brian hasn't cum, yet," she told the others. "This time. Somebody get some cameras in a good position. I'm going to blow him for the cumshot."

Oy, vey! After all that control, I was so built up, Jill was going to make me look like Vesuvius in 79 AD. And she knew all my secrets about how to force me over. I wasn't going anywhere any time soon, after she got done with me.

There was a general scramble while the others got the cameras and got into position for some really nice close-ups of Jill doing me. Jill had a smirk on her face that told me she was going to enjoy the hell out of dominating me. And she did. Dominate me and enjoy the hell out of it.

She got into a sixty-nine with me but with her ass raised just enough it was out of my reach. She got her knees on either side of me, then put her shins over my upper arms and shoulders to make sure I didn't get creative. She bent over and started in on me and given how cranked I was, I was hard in seconds.

I don't know if she and Annie had compared notes or what, but she started doing the deepthroat thrust followed by shallow bobbing around the head. When she was up near the head, she'd swirl her tongue around my glans, urethra and frenulum. When she took the deep stroke, she'd stick out her tongue and lick around the base of my cock, sort of reaching my sack. The combination was driving me crazy.

I was aware of three girls with cameras getting all kinds of close-ups as Jill just kept on doing me. Somehow she knew how to draw it out until I was ready to beg for mercy. When she sensed that, she finished me.

Hard, fast and deep sucking until everything pulled up and I was hitting that point of no return, when she sat up, still jacking me like crazy, and told the others "okay, ladies... here he cums!" and took me over the top by sticking her finger up my ass while aiming me at her tits and belly. I was shooting off like a cannon, with rope after rope landing all over her.

I couldn't see it, but I could sure feel it, and especially the prostate massage she was giving me. She kept milking me until there wasn't any more to get. Then she eased up and let me coast down. I was damn near blacking out.

"Yeah, I think Annie will be happy with that one," she told the others. I just gave up and collapsed. At some point she dismounted and sometime later we all got cleaned up. I was still really wobbly so I just parked myself in one of the gaming chairs and tried to recover my sanity.

It was still before midnight when Jill broke out the orange sherbet she'd brought for dessert and we all had some. Abby, Barb and Becca decided they were going to go on back to their place, while Jill decided to stay the night with me. Which was more than okay with me. The next day was Sunday and I didn't have classes, just work, so I could sleep in late even if she and I got rowdy later.

The girls got everything they were taking with them packed up and we each shared a hug and heavy kiss on their way out. Jill decided cuddling up and watching some kind of Rom-com would be nice and I agreed. It was after midnight when we knocked off, hit the bathroom, stripped off and climbed in bed. In a testament to her reasonableness, she had me do her like Annie would and spoon with her, docked. She felt wonderful and I fell asleep like that, completely and utterly blissful.

* * * * *

Sunday morning, Jill and I had a lazy wake up and screw, and then she headed off to take care of her stuff while I got some of my chores out of the way. I had work that night, so it was back to the usual grind for me.

Since the University was still on break, there weren't any earthshaking problems. Same for Monday, Tuesday and Wednesday night. Wednesday day before I'd left for work, I'd packed a bag for the Christmas stay at my folks'. I left on the six hour drive straight from work. I planned on being quiet and sneaking to my room for some toes up time before whatever was going to happen Christmas Eve Day.

Even with a decent playlist, my mind still had time to roam over how Annie and Jill's tête-á-tête had gone, and how Annie was truly going to react to the little orgy now captured in tastefully edited video on a flash drive in my backpack. If she truly wasn't jealous, and she and Jill had worked out whatever girl stuff had to be worked out, the three of us together could be a really wonderful thing.

Or, it could be the worst disaster in history. My history, anyway. I tried distracting myself with thoughts about the orgy and that didn't work. Or, actually it did work... my cock was having an argument with my belt and the steering wheel over territory. Painfully so at times. So I went back to listening to my tunes and blotting out reality for a while. I finally rolled into my parents' driveway just after 6am. It was still dark out.

I only had my backpack, so I eased out of the car as quietly as I could and let myself into the house. I still had a house key and made sure to be as quiet as I could. I navigated the darkened house up to my room and softly closed the door behind me. I turned on the lights expecting to see Annie in my bed, but she wasn't. So I set aside my pack, got undressed and crawled in, killing the lights. If I was lucky, they would see my car and know I was there, and be kind to me and let me sleep a bit. I was out of it within five minutes.

When I woke up, the sun was up and beating on the shades and I wasn't alone.

"Hey, Big Brother..." Annie voice came softly from beside me.

"Hey, yourself," I moaned a little as I turned to face her. Like me, she was naked under the covers. "Aren't you risking it a bit to be in bed with me at..." I had to look at the clock on the dresser. "Almost noon?"

"A little... but not really," she told me, leaning in for a kiss. Like I was going to refuse? Anyway, then she went on. "Mom and Dad know I find comfort in you, and feel safe with you. You aren't going to do anything out of line. I might, like slipping into your bed naked, but you'll be the gentleman and won't do anything I don't want you to do.

"And by the way, I'm supposed to tell you that brunch is available, and Kerry and Joel will both be here Christmas -- I guess Joel may get in tonight. I'm not sure. And if you're up for it, I've got some last minute shopping to do and I thought you could take me, just in case you wanted to get something, too. Like for Jill or something."

She was being all mature and sophisticated and everything, and her body was damn near quivering.

"Come here," I told her quietly, opening my arms. She was in my arms before I knew it. I didn't bother saying anything else. I just held her and let her hold me. She was literally shaking.

"I have missed you so much, Brian," she told my armpit.

"It hasn't been that long, Annie," I tried to reason with her. I should have known better.

"It has, too, when I haven't had you or Jill," she disagreed. I realized it would be a bad idea to argue.

"Did you and Jill get a chance to get together yesterday?" I asked. "And pretty soon you're going to have to let me make a dash for the bathroom."

Annie moved back out of my way and I could see the smile on her face as she told me, "yep! I'm muuuuch better now..."

Oh, thank God! I thought. That could have gone so wrong...

What I told Annie was, "Awesome! You know, you might want to throw some clothes on, because I'm going to pull on trunks and a tee, then head downstairs after the bathroom."

"Yep!" she told me and together we got out of bed, pulled on clothes and she headed downstairs while I headed for the bathroom. I caught up with her, and Mom, in the kitchen.

"Home the Conquering Hero!" Mom smiled to me. "After a hard semester battling Campus Dragons and protecting Fair Young... uh, Freshmen!" She put a cup of coffee in front of me. "Now expanding to Seniors." That one caught me by surprise and I must have shown it because Annie started looking embarrassed. "Annie tells me Jill is moving in with you."

Now Annie was turning beet red under my confused look.

"And don't give your sister a hard time," Mom went on as she started on an omelet. "It kind of slipped out after Jill's visit yesterday. Annie's elated to have an older woman in the household. And you won't get any grief from me... you're a twenty-four year old grad student who is paying his own way and can do whatever he pleases. As a busybody's aside, though, I do like Jill. I hope you two work out."

Then she turned her back to me to finish whatever she was cooking. Annie, on the other hand, mumbled "sorry..." I decided to go on the offensive.

"Why sorry?" I asked loud enough for Mom to hear. "You know Jill and I have kind of fallen for each other, she likes you, and I think the three of us can make life a lot easier for each other."

"God, I hope so," Annie told me and she wasn't trying to hide it.

"And yes, Mom," I decided to go on, turning to her, "Jill will move in when we get back, she'll cover her part of the expenses and chores, and probably keep on tutoring Annie like she has been."

"I suppose it would be tacky for your mother to point out it's a two-bedroom apartment," Mom sort of half-smiled. I think she was enjoying this.

"Not tacky," I told her. "Jill will be sleeping with me, when we're there at the same time. If I get too obnoxious, she can go sleep with Annie. But the point is, we're trying on living together. Not sure how much farther it's going to go at this point."

"Well, she seems like a nice girl," Mom told me as she put a Western Omelet, hash browns and OJ in front of me. "As I said, I hope it works out."

"Thanks," I told her. "We appreciate that." Then turned my attention to breakfast.

"I have some errands to run," Mom went on as I ate. "Joel will be coming in either late tonight or early tomorrow. Kerry will be here tomorrow morning. Your Dad had to go into the office this morning... I don't know why, being Christmas Eve and all, but who knows? In any case, he should be home by dinner. Whatever you're doing today, try to be back by six o'clock for dinner."

"Yes, ma'am," I told her and Annie echoed me with a "yes, Mom." That seemed to satisfy whatever Mom needed from us, so she went to get organized for her shopping trip. As soon as she was out of earshot, Annie turned to me.

"Mom's going shopping and Dad's at work..." she told me quietly. The intimation wasn't missed.

"Okay," I faux-grudgingly agreed. "But not more than an hour. I still have some last minute Christmas shopping to do. And then I've got to get everything wrapped. And..."

"Okay! Point made," Annie told me. "An hour of your hands, mouth and cock would probably kill me, anyway. But I do want to try something a little kinky... if you're willing."

"Obviously, it depends on what it is," I pointed out, "but generally, yeah... we can try out whatever kink you're interested in..."

Her grin threatened to split her face. "Finish eating and meet me in my room," she told me, then headed out. I figured I'd just do what I was told.

* * * * *

"I've been in acquisition mode," Annie told me as she pulled a locked toolbox out from under her bed. We were both standing there naked and I was already half-hard just from her pure beauty. She dug a key out of one of her dresser drawers and unlocked the box. It was one of the big, industrial strength Husky ones and I was extremely curious what it was that she would keep locked away.

"Most of this is for indulging fantasies after we're back down at school," she explained as she moved a bunch of sex toys out of the way so she could pull out a black velvet bag. "But there's one I want to try with you now, if you're okay with it."

"Okay, and that would be..." I prompted.

"This," she told me, pulling out a medium-sized jeweled stainless steel butt plug. "I want to put this in and have you fuck me doggy while I'm wearing it."

I didn't see anything particularly weird about it. So I figured why not?

"You probably want to clean out a bit, first," I suggested. "Might be more comfortable."

"Already did," she smiled. "And there's some Lynk lube in my nightstand drawer. And just thinking about it already has me dripping, so fuck the foreplay..." she told me. "If that's okay with you," she added a moment later.

In response, I walked over and took the plug from her, told her "up on the bed" and rummaged through her drawer for the water-based lube. She pretty much scurried to the center of the bed and got on her hands and knees, ass up and shoulders down, waiting for me. I damn near came just from the glorious vision of her in that position. She was naturally gaping a little and fuck! that was getting to me...

I lubed the plug and slid it in, accompanied by a slight moan from Annie. The plug popped into place and stayed put, so I got into position behind her and eased my swollen cock to her vestibule. She wasn't kidding about the already dripping. She was so lubed up, her thighs were glistening. So I went ahead and skewered her.

"OH MY FUCKING GOD BRIAN YES!!!" She wasn't being subtle. Or quiet.

I started stroking the way I knew she liked it, and a little bit later she was trembling. Probably a good sign. It was a little weird, feeling the hardness of the plug against the dorsal side of my cock, but it wasn't bad and Annie was rocking as if trying to intensify it.

"God, Brian," she moaned as she rocked. "That has to be the next best thing to a DP..."

"You want two cocks in you at the same time?" I asked. I had a mix of fantasy and jealousy rip through simultaneously, which surprised me.

"Well... yeah?" she answered a little timidly, still rocking and still breathing hard. "I hope that doesn't offend you..."

"Offend? No," I told her. "I'm feeling a little possessive, but I can probably work it out."

"Maybe I should buy Jill a strap-on," Annie mused. "Because fuck that feels awesome!"

"How do you know she doesn't already have one?" I asked, sort of being a smartass.

"Uh... I don't?" Annie answered. Then after a pause while we kept fucking, she asked, "would you like to be pegged?"

"I don't know," I told her honestly. "I've never done it. I've had a few fingers up there, when lovers discover what a little prostate massage will do to me. But nothing as big as a cock."

"Note to self..." she started.

"Uh-uh!" I interrupted. "No. Do not run out and get something to stick up my ass. We'll discuss it if and when the time comes."

"Awww..." she faux pouted. "Then I guess I'm just gonna hafta make do with you fucking the hell out of me while I've got a butt plug in..."

An only slightly subtle way of telling me to pick up the pace. So I did.

"Oh, fuck! Oh, yeah! Right there, Brian... right there! Oh fuck, you're gonna make me cum! Oh, God!..."

She went quiet and started slamming back into me in time with my thrusts. Until...

"Oh, fuck, YES! Yes! Yes! Yes-yes-yes-yehhh-ohhh FUCK! CUMMING!!!"

She went over hard and her sweet young pussy clamped down on me like squeezing a tube of toothpaste. I managed to hold off and not cum while she went over a second and third time. The third one did it to me. She was just too damned awesome to resist.

I'm not sure I moaned anything intelligible, but I stiffened up and drove deep into her pussy, grabbing her hips to keep her pulled back against me as I unloaded. Honest to God, there is nothing like cumming bareback in my sister. It was like my plug in her receptacle and some kind of cosmic circuit got closed! I came hard enough to start getting the tunnel vision and twinkly lights and shit.

Annie's legs were shaking so hard, it seemed like the only reason she was still up on her knees was because I was holding her there. And I was starting to lose it.

"Left," she mumbled and I took it that we should fall to the left, kind of like we'd done before. So I held her tight to me and fell left. She followed along and we ended up spooned with me still up her ass, the butt plug still in, and Annie trembling with the orgasmic aftershocks.

"God, Brian..." she moaned. "When I stop shaking, you can take out the butt plug. Fuck, that was intense! And thank you..."

"Thank me?" I answered. "For giving me another cosmic-level orgasm? No, sweetheart... thank you!"

"Thank you for helping with a fantasy," she told me. "And we're probably going to have to clean up and go shopping soon." I didn't answer. I just unceremoniously popped out the butt plug.

"Oh, GOD!" Annie yelped and I tried to hide the smile. "A little abrupt, don't you think?"

"Bathroom," I told her. "Shower. Dress. Shop."

"Yeah, yeah, yeah," she muttered, but she did get out of the bed, albeit a bit unsteadily, and toddled off towards the bathroom. I eased out of bed and followed.

* * * * *

"So how did it go with Jill?" I asked as we drove to the mall. "In detail, please. Mom kind of caught me flatfooted."

"Sorry about that," Annie muttered, then sat up a bit and started in.

"She got here early afternoon yesterday. I had her come in to meet Mom and Dad. They'd already met back at Thanksgiving and it was mostly chatter about what she was doing with school and the holidays and all. It was light and easy, and Mom at least is pretty impressed with her. I think Dad is, too, but he's a little harder to read. Anyway, she told them she wanted to take me out for lunch and some shopping and stuff and both Mom and Dad said they didn't have a problem with it.

"So we left and I let her get her seatbelt on before I hit her with the 'so what are the things we need to hash out?' question. Which incidentally, she laughed at. She started with picking a restaurant because she hadn't eaten and she said she was a bitch when she was hungry. We settled on Flannigan's because it's a great Irish pub and we could get some privacy.

"She started with the biggest elephant in the room and that was both of us loving you and what kind of territorial shit that would bring up. She asked me point-blank about how I felt about her usurping my 'ownership' of you... becoming the primary relationship in your life... and I admitted it pissed me off, but it pissed me off more that it was because I was scared. Scared of losing you. Her response was 'Oh, thank God.' When I told her to explain it, she basically said I was being honest and not bullshitting her or myself, and that was a great place to start from.

"I don't know if I want to get into all the details, but what it came down to was, I would never be your wife. Legally. And she conceivably could be, and have your kids and the rest of it. And that could drive a huge wedge between all three of us. But long before that, she and I had to agree on how to share you because she wasn't trying to cut me out of the picture. It's just, there's more pieces to the puzzle than just you and me. So it's really complicated.