The checklist
By Jason Sanders
Jtsanders403@gmail.com
I was at my friend Jon's 30th birthday. There were a lot of people, Jon is a successful investment banker and I'm sure there are a lot of heavy hitters here. I said hello to his parents, I'm 27 but we grew up next door to me and we were both only children so we kind of became like brothers. Now speaking of heavy hitters, let's see if I can find some girl to hit on who isn't with a husband or boyfriend. I seem to be one of the few people here by myself so I might not luck out tonight.
"Hey bro, how are you enjoying the party. Jon gave me a bear hug. He's packed on more than a few pounds while I managed to keep myself in very good physical shape.
"Good food, good drink now all I need is..."
"Some good pussy" he said to me. "Sorry, I've been looking around for you, I don't know who else is showing up but..." suddenly a woman, a blonde came up to him. "Happy birthday nephew."
"Oh, hey Jason, this is my aunt Annette."
"Nice to meet you" she said. As I said, she was blonde, not much older than me (I would find out later she was actually 39), nice rack, nice legs. I have a thing for older woman, so she was right up my alley.
"I'm really not his aunt, we are third cousins but when he was a kid, I was older and for some reason he called me Aunt Annette, so we've been keeping the joke all this years." She paused. She looked me over. "If you like, I could be Aunt is that floats your boat."
Bingo. Success. Score!
"Uh. Jason..." Jon started to say. That's when an older guy and his wife came up to Jon. "Sorry, I have to go, big money customer coming."
"That was good timing...for us. I get to know Aunt Annette better" I said.
There wasn't much I needed to know after that, we ended up back at my apartment (she's from Boston and staying with her sister for the party). For someone older, she wore me out, I mean, I fucked her in every position I knew, one I didn't know, and she also let me fuck her in the ass. I shot at least three times and she had a whole bunch of orgasms.
"Wow" she said. "You managed to get me out of breath. And I could use some help on that cock of yours ( 9 inches). I mean, I figured you might be well hung, but really."
The following Friday I took Amtrak to Boston. We went out to eat, went to a comedy club and mostly I just fucked the hell out of her. I was going to head home Sunday, but she told me to hang out to Monday morning. She had a surprise for me, one that would start Sunday afternoon and probably go late if I was lucky. I had no idea what she was talking about, I mean I've already fucked her ass.
The surprise happened Sunday around 3 when there was a knock on the door. A woman, redhead, maybe about Annette's age came in. "Hi, I'm Sandy, Jesus, Annette, he is hot. Got to see if what you told me is true also."
"Surprise" said Annette as she put her arms around me. "I said I might need some help with that cock of yours and help is here." Holy shit, I got a threesome? I lucked into one when I was 24 but didn't think it would happen again. Sandy grabbed me and kissed me. Then Annette and Sandy began making out.
"Like what you see" said Annette as she took Sandy's clothes off.
"Oh dear, he's wearing jeans, he's probably ready to burst" said Sandy who was down to her panties. Big, I mean D or DD tits. When she took her panties off, I could see the carpet matched the drapes. She undid my pants, Annette who was naked at that point took my pants off.
Sandy stretched my boxers to get my already erect dick out. "Jesus, nice cock."
"They looked at me slyly and began making out on their knees with their hands on each other's tits. "Wow," said Sandy" you weren't kidding Annette. Let me get some of that big boy. She practically devoured my cock, so we were in deep throat territory. What she couldn't get in Annette was licking. Wow, a nice double BJ. She took me out of her mouth and began kissing me, I sucked on her tits and made my way to the promised land. I ate her pussy out and she was screaming. "Shit, yeah, oh fuck, damn he's better some girls, I've been with."
"Told you"Said Annette as she joined me feasting on Sandy's pussy. Obviously, she didn't bother to tell me until now she was bi but I wasn't complaining as I fucked Sandy while she ate Annette's pussy. I came in Sandy's mouth who passed it on to Annette. Then they went at it until I was ready to tag back in. Annette laid on top of me, "Worth staying overnight" she asked me. That had to be a rhetorical question. I decided to remote Monday, so I didn't have to leave until noon. That gave us some more fuck time and a talk.
"I hope you enjoyed that. I am bi, Sandy and I hook up occasionally when her husband is away. She doesn't like to do their Saturday night thing without him, and I thought you might like that. That your first threesome?"
"I'll never tell."
"Well, I hope this was better than that first one. Another thing, their Saturday night thing is a swing club, they host about 10-12 people and yes, I have been there and partaken in it. Just so you know." I said that it was okay by me and jokingly said, don't let me hold you back, I'll go with you.
Well, the next weekend she actually took me up on my half-jokingly okay let's do it bringing me to Sandy and Andy (yes, her husband's name is Andy). We got there, and it was check your clothes at the door because everyone was naked except for some sexy lingerie for women (and one guy who was wearing women's yellow panties. Not to self, avoid at all costs), I met Andy, he was eyeing me head to toe. Hope he's not bi also. Annette was taken to one of the side rooms by a woman and man, so I was planning on joining them when I got sidetracked by this couple. Late 30's. She had brown hair, her smaller tits covered by her lingerie, and I noticed that a few people my age were not circumcised. "You must be Annette's new boy toy; I think she's somewhere enjoying herself and we figured we would take care of you ourselves."
Ourselves, I did not like the way he was staring at my cock. "You like cock" he asked pointedly to me.
"I like pussy" I shot back.
"That's okay, we can do it without him, he'll just stay on the side and watch us." What the fuck did I get myself into. Not only was I not doing him I would be doing her with him watching. I shook them off and went to look for Annette. When I entered the room, the woman was between her legs and the guy's cock was in her mouth.
"Oh baby, I thought we had someone lined up for you. I didn't mean to leave you high and dry."
"Don't worry Annette, I can take care of your boy," said the woman. So, I was having sex with some woman whose husband was fucking my girlfriend in the other bed. Not one of my best performances.
On the way home Annette said "I am so sorry. I forgot that you've never done that before and I shouldn't have walked off with them before I made sure you were set. If we ever go again, I will make sure I am there or someone has you, as long as we always come back to each other at the end of the night."
So, we went to sleep, and I woke up at 10 and showered. I got out and found she had cooked an omelet ,home fries and bacon and coffee for me. "Figure you needed a boost after last night." She sat down.
"You didn't warn me I would have a guy or two hit on me. I mean one guy asked me "do you like cock."
"I take it you didn't take him up on that?"
"No, I can't say I haven't thought about it but if I were to ever consider it would have to be about 10 things on the checklist."
"Like what?"
"I don't know. I guess it would be with you, I don't think I'm ready or able to solo. It would have to be someone I don't know and someone I don't have to see again." "I guess a foursome with Andy and Sandy is out?"
"Not only that but I want a clean shaven, not hairy and circumcised. I don't think I can handle a foreskin'"
"So those take Andy out of the running for sure. I mean I've been with guys both ways and I think I get the appeal of circumcised cock."
"Oh, I definitely don't take it in the ass."
"Okay but I have to tell you, I enjoy it and I don't have a prostate to get rubbed." She laughed; I gave her a look like, not happening.
The following weekend I had work I had to do on site, so we didn't get together, I did get a call from Jon asking if I wanted to go out for drinks Saturday.
"So, you still fucking my cousin" he asked.
"Yeah, I mean it's just sex, it's not a lifelong commitment."
"Uh, do you know about some of her friends?"
"You mean do I know she got into swinging with her ex-husband, and she still does from time to time?"
"Yeah, I don't think he dragged her in kicking and screaming. And she does like younger men, and she has always been a bit sexually adventurous, in fact I don't think I should tell you this but remember when I was 18 I told you I lost my virginity?"
I thought for a second "Yeah, you were kind of excited and ....oh shit, did she pop your cherry?" He nodded. "Your own cousin?"
"Third cousin. Once removed."
I went to her the following Friday night. I asked her if she did that and she said that Jon was kind of down in the dumps so She'd figured she would cheer him up for his birthday and that was the best way she could. I was starting to wonder if I should get out this when I get a chance except, she is so fucking good in bed. She can give a blow job that would suck the chrome off a motorcycle. Her snatch grabs my cock, and her legs just pull me in further. Not sure if I want to give up that just yet,
Saturday, she said she had a surprise for me. I figured we were going to Sandy and Andy's, but we weren't. There was a knock on her door. A guy I don't know came in. "This is Ben, he meets all your checkboxes. I figured I would let it be a surprise than let you stress over it."
"Hi, nice to meet you" said Ben shaking my hand. Am I going to actually have sex with this guy? Annette said to me to do what I want to. At worst we would just spit roast her. Now like I said, I was ready to bail but I figured what the hell. I don't know this guy; I won't have to see him again and I take it he meets all the checkboxes. So after some alchohol and ecstacy Annette did a strip for us and pulled me up to her and kissed me as she took my shirt off. Ben came over and kissed Annette and then...kissed me.
I surprisingly didn't recoil all that much. Annette kissed me again and then we had a threesome kiss. Annette had loosened my pants which I stepped out of and next
thing all three of us are naked. Annette grabbed our two cocks and began rubbing them together. Then she dropped to both knees and began sucking us both off. Then Ben dropped down with her and holy shit... he's blowing me. And not too badly. Annette came back up and began kissing me while he blew me, and I sucked on her tits.
I went down to her pussy and was met by Ben's cock in my face. Annette got down with me began blowing him and then passed the joint to me. I hesitsted but between the alchohol, ectasy and generl curiousity I opened my mouth and began sucking.
"Yeah baby, you're doing a great job" she said. She was making out with Ben who was enjoying himself. I got into the rhythm of sucking cock, and she kissed my ear while I did it. He was rock hard, and he stiffened and he splooged over my mouth, Annette's mouth and I ended up swallowing some. She licked the cum off my face and then the two of them blew me. I was very hard, and he asked me "want to put that in my ass?" Condom on, a little lube and I was in him. Fucking a guy. In the ass. And I like it, after a while I pulled out, he sucked me until I came, and he swallowed, and we kissed.
He left a little while later and Annette sad "I had a feeling you would go for it when you gave me that checklist."
"I didn't think it would actually happen, but I guess my curiosity has been satisfied?"
"Satisfied?" she asked.
So, the following week we're at the swing cub. Annette introduces me to a guy; I don't know and meets the checklist and I soloed while she ate his girlfriend's pussy out in the same room. The girls would throw out tips to us as a joke and when I bent over and took it in the ass Annette came over, buried her pussy in my face and asked me if I liked it. I told her I would have to try some more times to make sure.
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