Overnight sex

Sunday, May 25, 2014
Kris: I woke up in the middle of the night and saw that there was a lady laying next to me… 7:27 AM
Kris: I didn’t know her, but I could tell it was a female cuz she was lying on her back and had really big boobs! 7:29 AM
Kris: instead of being scared I started wondering what it would be like to have sex with her. 7:31 AM

Kris: I was a little nervous…but I reached over and started caressing her tits, gently rubbing, feeling, pulling a little on her nipples. 7:35 AM

Kris: her nipples got hard… 7:36 AM

Kris: she started to wake up… 7:37 AM

Kris: I got scared for a minute thinking she might beat me up…when she realized what I was doing… 7:38 AM

Kris: instead…she started humming when I moved over to lick her nipples  7:40 AM

Kris: …first one…then the other…back and forth…she kept humming and moaning quietly…made little “body jerks”…groaned “oohh” and spasmed quickly…body jerked a little. 7:46 AM

Kris: I wondered what was between her legs…in the movies I had seen it was always covered up… never watched much porn. 7:49 AM

Kris: So I took a chance…reached down to feel it… 7:49 AM

Kris: felt really good… 7:50 AM

Kris: slipped two fingers inside…she was already really wet, tight…thrust my fingers in and out…deeply…steady rhythm…in and out…she moaned… 7:54 AM

Kris: she rolled on her side, lifted one leg, as if inviting me inside her. she grunted something 8:00 AM
Kris: I thought “who cares?…i’ll just go in from behind and give her a good fucking that way…lying here on our sides” 8:03 AM

Kris: so I slipped my hard cock in her…from behind 8:05 AM

Kris: I was a little nervous about what she would do if she didn’t like it…maybe try to bite my cock off or something (though i couldn’t really see her teeth in the darkness). 8:10 AM

Kris: anyhow…I kept thrusting in and out from behind…she groaned and seemed to really like it… 8:12 AM

Kris: she was building in excitement…then suddenly exploded into orgasm…made loud noises and scared the shit out of me…never saw anything like it before (but always wanted to… 😉  8:16 AM

Kris: after she finished cumming I kept thrusting…then I came…it felt SO GOOD!…and then I thought of the words to an old pop song… 8:20 AM

Kris: …”We did the Mash, we did the Monster-Mash. We did the Mash, it was a graveyard smash!”… 8:23 AM

Kris: Alfalfa… 😉 8:23 AM

Kris: Boat fired right up! WHOOPEE!!! ROCK ‘N ROLL BABY! 1:45 PM

Me: Yay! I’m having lunch in the park with my niece. 1:46 PM

Kris: Sounds nice. My silly “story” was an effort to “normalize” your feelings about the whole sleeping with me all night thing.  Hope I didn’t offend or hurt your feelings in any way. 1:51 PM

Kris: Tell me if I did…even a little…so I can apologize. Never want to hurt you in any way. 1:55 PM

Me: Awww…You’re so sweet. The story was a little odd but the funny and sexy parts were hot! Thank you! ! 1:59 PM

Kris: Ok…long as it didn’t offend. “Odd” makes me laugh…be curious to hear you explain how so a little. 2:02 PM

Kris: Beautiful, sunny day…off to roto-till garden and cut huge lawn. Be fun to have you see it…which will be completely possible after June 16th…when wife is gone full-time. Maybe even an overnight or two…if u decide to venture out of your comfort zone. 2:09 PM

Kris: Off to gym for a bit…enjoying your day? 3:44 PM

Me: There’s something about a little girl that makes everything fun! 4:27 PM

Kris: Good! we all need fun…glad you’re having some! 6:28 PM

Kris: …and I bet you’re a fun aunt!…”Ahnty Sassy”… 😉 6:43 PM

Me: You betcha! Done with niece, heading out for supper. Chat later? 6:48 PM

Kris: Sure…had big ambitions for lots of chores…but not the strength today…so just “chillin” rest of night. Love to chat!…’bout what time? 6:53 PM

Kris: Text me when you’re home & ready to chat… 🙂 8:40 PM

Me: I am home and ready to chat. 🙂 9:13 PM

Kris: K. 🙂 9:15 PM
·       May 25 9:18 PM Kris: Hi!
·       May 25 9:18 PM Sassy: Hiya Kris sweetie honey darling dear
·       May 25 9:18 PM Kris:  : ) 
·       May 25 9:19 PM Kris: you make me laugh!
·       May 25 9:19 PM Sassy:  : ) 
·       May 25 9:19 PM Kris: wassup?
·       May 25 9:20 PM Sassy: Very quiet. How’s your chillin going?
·       May 25 9:20 PM Kris: ok…watching a movie and chatting with you!
·       May 25 9:20 PM Sassy: I wish you were here so I could fish your beautiful cock out of your plaid boxers.
·       May 25 9:20 PM Sassy: What movie?
·       May 25 9:20 PM Kris: wait let me back up…my my…you’re Sassy tonight!
·       May 25 9:21 PM Kris: Gettysburg
·       May 25 9:22 PM Kris: just checked…boxers ARE plaid again…I think once they were solid
·       May 25 9:22 PM Sassy: There was some big anniversary this year.
·       May 25 9:22 PM Sassy: They were light blue/gray once
·       May 25 9:22 PM Kris: you’re too funny!
·       May 25 9:23 PM Sassy: But not the night I attacked your belt buckle and sucked on you within the first 3 minutes you were in my room
·       May 25 9:23 PM Kris: Mmmmm…you Sassay girl!
·       May 25 9:24 PM Sassy: I am not funny. I am Sassy!
·       May 25 9:24 PM Kris: Right!
·       May 25 9:24 PM Sassy: and sexy
·       May 25 9:24 PM Kris: right again!
·       May 25 9:24 PM Sassy: and sultry
·       May 25 9:24 PM Kris: Mmmmm!
·       May 25 9:24 PM Sassy: and a lot of other S words!
·       May 25 9:24 PM Kris: like what?
·       May 25 9:24 PM Sassy: Smart
·       May 25 9:25 PM Kris: yes!
·       May 25 9:26 PM Kris: whatcha thinking lately?
·       May 25 9:27 PM Sassy: trying not to. Except for you and me and BOOM!
·       May 25 9:27 PM Kris: OK!
·       May 25 9:27 PM Sassy: Did you get the back 40 mowed?
·       May 25 9:27 PM Kris: no…just went to gym, came home, covered boat, ate…nothing more
·       May 25 9:28 PM Kris: tomorrow wife’s going to mow while I roto-till the garden
·       May 25 9:28 PM Sassy: I had so much fun with my niece. She is so amazing!
·       May 25 9:28 PM Kris: watcha do?
·       May 25 9:29 PM Sassy: We picked up lunch from McD’s and sat in the park to eat
·       May 25 9:30 PM Kris: what was so amazing and fun…like what?
·       May 25 9:30 PM Sassy: She showed me how the various playground equipment works
·       May 25 9:31 PM Sassy: She has taken gymnastics and gone rock climbing so she was explaining how what she learned from that applies to this
·       May 25 9:31 PM Kris: did that make you laugh…because she’s so smart?
·       May 25 9:31 PM Sassy: I try to take her seriously… she is so grown up sounding.
·       May 25 9:32 PM Sassy: Then we went to RiteAid and I let her buy stuff!
·       May 25 9:32 PM Sassy: We got a bead kit to make jewelry and CANDY and… a Hula hoop!
·       May 25 9:32 PM Kris: Wow! You really ARE a fun aunt!
·       May 25 9:33 PM Kris: Does she call you “aunt” or “auntie”?
·       May 25 9:33 PM Sassy: No. Just my name
·       May 25 9:33 PM Kris: Just your first name?
·       May 25 9:33 PM Sassy: yes
·       May 25 9:34 PM Sassy: She made a necklace with her name. 
·       May 25 9:40 PM Sassy: Hubby came out and showed niece how to play with kitties… it was very fun
·       May 25 9:40 PM Kris: came out to where?
·       May 25 9:41 PM Sassy: of his office to the living room
·       May 25 9:42 PM Kris: gotcha…was that a little different…or something he would normally do?
·       May 25 9:42 PM Sassy: very different. He usually hides when I have company
·       May 25 9:42 PM Kris: well…that was nice then!
·       May 25 9:42 PM Sassy: She bought three bags of candy, and she carefully opened them and took three pieces from each and went in to share with him
·       May 25 9:43 PM Kris: did that help lure him out?
·       May 25 9:44 PM Sassy: Yep
·       May 25 9:44 PM Kris: cool!
·       May 25 9:45 PM Sassy: He was “talking for the cats”
·       May 25 9:45 PM Sassy: It was hysterical
·       May 25 9:45 PM Kris: I bet!
·       May 25 9:45 PM Kris: was she really amused?
·       May 25 9:45 PM Sassy: Yes. She was giggling and talking back “to the cats”
·       May 25 9:46 PM Kris: had she played with the cats before?
·       May 25 9:46 PM Sassy: not like this. Last time she sat and petted them, but she had them jumping and chasing string and really interacting this time
·       May 25 9:47 PM Kris: sounds like lots of fun…and nice that hubby joined in…
·       May 25 9:48 PM Sassy: I was sitting in the recliner
·       May 25 9:49 PM Sassy: Remembering your kissing me there
·       May 25 9:49 PM Kris: when were you remembering it?
·       May 25 9:49 PM Sassy: this afternoon
·       May 25 9:49 PM Kris: when your niece was there…and hubby was playing with her?
·       May 25 9:50 PM Sassy: She was in the room, working on her necklace
·       May 25 9:50 PM Kris: hope it’s a nice memory…sexy memory…
·       May 25 9:50 PM Sassy: Very
·       May 25 9:50 PM Kris: good!
·       May 25 9:50 PM  Sassy: sensual
·       May 25 9:51 PM Sassy: Kind of astonishing for a man who was like… kissing… eh… when we started talking
·       May 25 9:51 PM Kris: workin on it…lol
·       May 25 9:52 PM Sassy: yum. adore helping you practice. 
·       May 25 9:52 PM Kris: I think you converted me within about a couple of hours of the very first lunch meeting.
·       May 25 9:53 PM Kris: starting when you kissed me right outside the restaurant…completely took me by surprise…mesmerized…in a trance…you’re a snake charmer!
·       May 25 9:54 PM Kris: then got hotter in the parking garage…can’t believe I did that…but glad I did!
·       May 25 9:54 PM Sassy: me too
·       May 25 9:56 PM Kris: glad you like helping me practice…more “practice”…Tuesday…then day together Thursday…been thinking about that
·       May 25 9:57 PM Kris: sure you want to use up so much of your vacation time with me?
·       May 25 9:57 PM Sassy: Definitely!
·       May 25 9:57 PM Kris: alrighty then!
·       May 25 9:57 PM  Sassy: Did you read the story I sent?
·       May 25 9:59 PM Kris: not yet…but I will…do you want me to now…or later?
·       May 25 10:00 PM Sassy: whenever
·       May 25 10:00 PM Kris: give me a couple of minutes. I’ll go read it right now…hold on…
·       May 25 10:08 PM Sassy: Took a bathroom break… be back soon… keep typing if you like and I will catch up
·       May 25 10:10 PM Kris: Wow! You’re a great writer and that was a really sexy story. It was fun to see “some parts of you I’m starting to know” in the story…as well as looking for “little clues” about what turns you on…what you might like to do when we’re together…the only thing is that the pics didn’t display…maybe if I copy and paste them separately into my browser…yummm!
·       May 25 10:11 PM Kris: the woman in the story got herself off…something I’d still like to see you do…which so far you’ve still replied with “we’ll see”
·       May 25 10:13 PM Kris: when we were in the shower together…and you started to…you stopped…you said it was because “you didn’t want to fall”…but I think you got self-conscious…maybe you won’t be at some point.
·       May 25 10:14 PM Kris: then there’s me “telling you a story” or “talking to you”…while we’re lying together naked on the bed…kind of weird to have you “write a script” for me…but could use at least a LITTLE help…with what would turn you on…you’d want to hear.
·       May 25 10:15 PM Kris: ok…I’ll wait for you to get back…read this…and reply…
·       May 25 10:18 PM Kris: Oh goodie!…tried again and the photos DID display…very sexy…sensual…whole setting…leads me to think again about Thursday…know how the boating part will go…just wondering about sex that day…how/when/where…
·       May 25 10:18 PM Kris: lots of content above…don’t miss anything! LOL
·       May 25 10:19 PM Kris: ok…I’ll really wait now…for you to reply…
·       May 25 10:20 PM Sassy: I’m baaaaack!
·       May 25 10:21 PM Kris: great!…plenty to catch up on.
·       May 25 10:21 PM Sassy: You are so fun… I disappear for a few minutes and you bring up 6 different ideas!
·       May 25 10:22 PM Kris: because you’re smart enough to not miss any…except any you might want to avoid…then you’re really good at “subtly dodging”…wink!
·       May 25 10:22 PM Sassy: thank you for reading my story, and liking it
·       May 25 10:22 PM Kris: it was GREAT!
·       May 25 10:23 PM Sassy: I don’t know where these things come from… they just pour out of my head
·       May 25 10:23 PM Kris: and maybe some other parts?
·       May 25 10:23 PM Sassy: Ha ha. Naughty man
·       May 25 10:23 PM Kris: so you get turned on thinking/writing it?
·       May 25 10:23 PM Sassy: I will try to help you with talking more
·       May 25 10:23 PM Sassy: Yes
·       May 25 10:24 PM Kris: do you get off?
·       May 25 10:24 PM Sassy: tingle a bit
·       May 25 10:24 PM Kris: not to orgasm?
·       May 25 10:24 PM Sassy: Not usually
·       May 25 10:25 PM Sassy: It’s a little short and cute for that
·       May 25 10:25 PM Kris: but you can get off just using your imagination…right…without even touching yourself?
·       May 25 10:25 PM Sassy: Oh yes
·       May 25 10:26 PM Sassy: Sometimes videos help
·       May 25 10:27 PM Kris: I just can’t imagine that…I was actually thinking about how you could do that when I was taking a shower today…amazes me…no way I could do that…without at least SOME physical stimulation.  I can get a little “pre-cum” flowing…but not all the way to an orgasm without some kind of touching.
·       May 25 10:27 PM Sassy: What do you think about, when you’re taking care of yourself.?
·       May 25 10:28 PM Kris: women I’d like to fuck…sometimes from the past…sometimes from the present…usually someone I know well…but I’ve also looked at porn in the past…not so much recently.
·       May 25 10:29 PM Kris: sometimes past sexual experiences…like with wife from years ago…when we were younger…a variety of things…
·       May 25 10:29 PM Sassy: Cool
·       May 25 10:29 PM Kris: now…sometimes YOU!
·       May 25 10:29 PM Sassy: Really?
·       May 25 10:29 PM Kris: Sure!…why would that surprise you?
·       May 25 10:30 PM Sassy: I like to inspire you
·       May 25 10:30 PM Kris: you do!
·       May 25 10:30 PM Kris: you do more than that too…up close and personal!
·       May 25 10:31 PM Kris: what kind of videos help you?
·       May 25 10:32 PM Sassy: It depends. Sometimes snippets from TV shows of people kissing… very tame. Other times, very raunchy outdoor sex or BDSM with ropes and stuff…
·       May 25 10:33 PM Kris: would watching something with me be fun…or not?
·       May 25 10:34 PM Sassy: Could be… never done that.
·       May 25 10:34 PM Sassy: I’ve shared videos and emailed comments back and forth, but never watched with a man
·       May 25 10:35 PM Kris: why watch a video when you can grab the real thing, eh?…but might be fun…something different…
·       May 25 10:36 PM Sassy: Have you watched with a woman?
·       May 25 10:38 PM Kris: years ago with my wife…we watched porn…like rented a movie in a hotel room…when we were just staying someplace…and porn was something you could buy there.
·       May 25 10:38 PM Sassy: As foreplay?
·       May 25 10:39 PM Kris: yes…not during…would naturally fuck after…but not during or to get off while watching…actually helped make the sex hotter…but then she’d always “feel guilty” after…oh well…
·       May 25 10:39 PM Sassy: guilty for what?
·       May 25 10:40 PM Kris: good girl “stop it I like it” syndrome…like how the demure lady might feel…if she was too much in charge at a given moment…suppressing Sassy.
·       May 25 10:40 PM Kris: that make any sense?
·       May 25 10:40 PM Sassy: Yes
·       May 25 10:41 PM Sassy: I talk with a lot of guys in chat who have very repressed wives
·       May 25 10:41 PM Kris: my wife actually LOVES sex…what’s weird is…she doesn’t like to talk about it or admit it…and I tease her mercilessly about that…
·       May 25 10:42 PM Sassy: I like all three… sex, talking, admitting!
·       May 25 10:42 PM Kris: I’ve noticed
·       May 25 10:43 PM Kris: I like talking here…but not used to talking “during”…which you’ll need to help me with a little…and I’ll have to get used to…just not used to it…but willing to learn…grin!
·       May 25 10:44 PM Sassy: Maybe we can try sex during talking. 
·       May 25 10:44 PM Kris: talking about what?
·       May 25 10:45 PM Sassy: probably… the weather?
·       May 25 10:45 PM Sassy: 😀
·       May 25 10:45 PM Kris: now you’re teasing me!
·       May 25 10:45 PM Sassy: ayup
·       May 25 10:45 PM Kris: ok…so back to something we said we were going to do…
·       May 25 10:46 PM Kris: I’m going to put my cock in your mouth as your head is over the side of the bed and lick your nipples while you suck on me and grab me…how’s that sound?
·       May 25 10:48 PM Sassy: Yummy
·       May 25 10:48 PM Kris: but only as foreplay (hopefully)…
·       May 25 10:48 PM Sassy: right
·       May 25 10:49 PM Kris: I had a little fantasy about using one of the toys at the same time…
·       May 25 10:49 PM Sassy: I am just too good at bj?
·       May 25 10:49 PM Sassy: OH my… you have good ideas
·       May 25 10:49 PM Kris: yes…I might not want you to stop…but then I’ll be “done”…and don’t want to be that soon.
·       May 25 10:49 PM Kris: my “recovery” time is much longer than the guy in your story…lol
·       May 25 10:50 PM Kris: I was thinking the fake cock in you might be fun to try…since you’re a “vagina girl” (that word you don’t like)…
·       May 25 10:51 PM Sassy: Interesting. Remind me to get it out, with the lube, so it’s there if you want to grab it
·       May 25 10:52 PM Kris: ok…in your story there was “front and back”…was back anus?
·       May 25 10:52 PM Kris: ass…hole…whatever!
·       May 25 10:53 PM Kris: language is funny sometimes
·       May 25 10:53 PM Sassy: don’t think so… where was that?
·       May 25 10:54 PM Sassy: Wait… I see it.
·       May 25 10:55 PM Kris: a few sentences above the last picture…
·       May 25 10:56 PM Kris: “added my fingers inside her front and back”
·       May 25 10:56 PM Sassy: Yeah
·       May 25 10:57 PM Sassy: You do catch the sassy details
·       May 25 10:57 PM Kris: “until she came again” (AGAIN!  I’m still waiting for once!…not your fault…combination teasing…”self-deprecatory” you told me to stop)
·       May 25 10:58 PM Kris: so I was thinking of putting my finger in your ass sometime…but know you had a bad experience…and with me it will be gentle and not hurt…lots of lube…slow…in there without hurting…if you want to try it…could do me again too…but need more lube next time…or not…whatever
·       May 25 10:59 PM Sassy: sure
·       May 25 11:01 PM Sassy: check in first… I am having… um… intestinal problems today but I hope they’ll be healed soon
·       May 25 11:02 PM Kris: ok…will check in first…on a different subject… I may have to wait till Tues…to get this out of you…but any thoughts about sex on Thursday?during… after… boating… when/where? We could “fool around” just about anyplace…but would like more comfort for “full sex” than I can picture on boat…and thoughts about that?
·       May 25 11:02 PM Sassy: What would you consider ideal?
·       May 25 11:03 PM Kris: a comfy bed someplace
·       May 25 11:04 PM Kris: one option would be get a room after boating…but you go home after…if you’re not comfortable spending the night.
·       May 25 11:06 PM Kris: just a thought…money’s tight…but this is going to be a “really fun fantasy” for me…so trying to play it all out in a certain way would be worth it for me.
·       May 25 11:07 PM Sassy: I am worrying about money. And it being commencement weekend down here, will have to get far away to even find a room
·       May 25 11:07 PM Sassy: Let me think some more
·       May 25 11:08 PM Kris: I’m strapped for cash right now…but get paid next Friday…if you could afford to put a room on a credit card I could reimburse you as soon as next Saturday.
·       May 25 11:09 PM Sassy: Sure
·       May 25 11:09 PM Kris: Do you want to stay near Boston?…go on the Charles River…out to Boston Harbor…or go to the Cape?
·       May 25 11:10 PM Sassy: in the boat?
·       May 25 11:10 PM Kris: yes
·       May 25 11:11 PM Sassy: It’s very hard for me to decide
·       May 25 11:11 PM Kris: why?
·       May 25 11:11 PM Sassy: I don’t know anything about this
·       May 25 11:12 PM Kris: what’s to know? where would you prefer to go…see…be…to see things? if you haven’t been to either (which you haven’t),,,,both would probably be equally fun for you.
·       May 25 11:13 PM Kris: I would prefer the Cape…but you might like to cruise the Charles… seeing the city from the river is very different…fun.
·       May 25 11:13 PM Sassy: I think up here. Would be fun to see places I know from a different perspective
·       May 25 11:14 PM Sassy: I’ve never been to the cape
·       May 25 11:15 PM Kris: ok…we’ll stay up here…and you’re right!…it’s fun to see places you know from a different perspective.  I think you’d love the Cape…very beautiful…but we can do that another time (hopefully).
·       May 25 11:15 PM Sassy: Sure
·       May 25 11:15 PM Sassy: If I survive this trip. 
·       May 25 11:15 PM Kris: You mean live…as in not die?
·       May 25 11:16 PM Sassy: Right… or get horribly sunburnt or seasick…
·       May 25 11:16 PM Sassy: What I am supposed to wear? I don’t think I have any boating clothes.
·       May 25 11:18 PM Kris: Whatever you’re comfortable in…just for being outside in general…nothing special for “boating” per se…cover up if that helps with concern about sun…plus I don’t think it’s going to be too hot…so you can probably cover up and be comfortable.
·       May 25 11:18 PM Kris: have you been on any kind of boat before at all?
·       May 25 11:19 PM Kris: you mentioned concern about getting sea sick…that”s why I asked if you’ve been on a boat before.
·       May 25 11:21 PM Sassy: Here and there… whale watch, ferries, glass-bottom boat in the Keys
·       May 25 11:22 PM Sassy: The Lake W tour boats
·       May 25 11:22 PM Sassy: Attempting to water ski with cousins in NC as a teenager
·       May 25 11:23 PM Kris: ever get sea sick any of those times?
·       May 25 11:24 PM Sassy: Yes
·       May 25 11:24 PM Kris: easily…sometimes? a lot?
·       May 25 11:24 PM Sassy: sometimes
·       May 25 11:24 PM Sassy: If I stay above decks where I can see the horizon, I’m usually fine
·       May 25 11:25 PM Kris: there’s no “below deck” on my boat…in fact, you’ll probably be sitting on the front bow…out in the open…
·       May 25 11:26 PM Kris: I want this to be fun for you…if it’s not…we’ll turn around and do something else…don’t worry…no point otherwise.
·       May 25 11:26 PM Sassy: I plan to be fine. 
·       May 25 11:26 PM Kris: I want you to suck on my cock…not throw up on me…LOL
·       May 25 11:27 PM Kris: I don’t know what’s gotten into me tonight…some “Sassy” wearing off maybe?
·       May 25 11:28 PM Sassy: Hope so!
·       May 25 11:28 PM Kris: how u doin…getting tired?
·       May 25 11:28 PM Sassy: Yeah…
·       May 25 11:28 PM Sassy: didn’t sleep much again
·       May 25 11:28 PM Kris: ok…let’s say goodnight…Mwah!
·       May 25 11:29 PM Sassy: So good talking! Sweet dreams!
·       May 25 11:29 PM Kris: Same…you too!

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