A trip out of town doesn’t disappoint

I went away for a weekend with a girlfriend to New York City. this gf is also a divorced mom w kids and we get together to tear it up. this weekend ended up a little differently though…

i have a guy from my first job after college with whom i’m friends – he was in product development and i was in marketing communications. we were never intimate but there seemed to be a bit of the good ‘ol sexual tension in the air. although nothing ever happened with that because he got engaged & married right away. it’s been YEARS since we last saw each other but through the magic of fb we stayed friends. we don’t live in the same city anymore and in recent years he’d gone through a separation and subsequent divorce from that college sweetheart. he happened to be in NYC the same weekend we were and so he invited my gf and me over for drinks at his pied a terre. we went and all of us caught up on our lives and were enjoying the nice bottles of red and the charcuterie plate he set out. lots of good times and laughs.

when he went in for another bottle, my gf leaned over to me and said, “you guys need each other. he’s very lonely. and i know despite your tough act you’re lonely too”. that actually made me choke up! she was right. i’ve been wanting to spend time with one person and while fully aware this friend was not that goal, i knew she was right. he returned and she politely bowed out, taking a cab back to our hotel.

we chatted for a while longer and a few more glasses later we both acknowledged that it was getting late. he offered me to crash there and i took him up on it. i changed into a borrowed T shirt and crawled into bed. he got ready for bed as well and crawled in next to me. we snuggled for exactly 2.5 seconds before the kissing started. it was very niiiice.

i must give a lil background here: Brand is a brainy guy. hot, successful, a dream in many ways. he shared with me that he had not been with another woman since his wife – and they were together for 19 years. um, WHAT?! that’s a helluva lot of pressure to lay on a girl. given i was not expecting this i did not have supplies. given that he was not a player he did not have supplies. Anita don’t bareback ANYONE, not even a celibate man who hadn’t had sex in the last 3 years with his wife and who’d been divorced for a year. He’s a real great guy who focused on work and trying not to be depressed at his lack of intimacy – can you imagine relying solely on masturbation for getting off?? I can’t. well, i told him it was up to him if he wanted to have sex, that i was up for it if that’s what he wanted. but if that’s what he wanted we would need to go somewhere and get condoms. he absolutely did. ok, so now at about 3 am on a saturday night, we got out of bed. i put on the tshirt and my heels and my blazer. he dressed in somewhat normal clothes. we jumped into the cab and drove to CVS.

at CVS we must have looked like total idiots. uh huh. you KNOW why we’re there based on what i’m wearing. we find the condoms right away and guess what was playing on the Muzak? Damned Lionel Ritchie singing “Eaasaay. I’m easy like Sunday mooorn’aan, yeeeaaah”.

i nearly peed my pants. it wasn’t bad enough for me to be doing the “strut of fuck yeah” (the walk of shame to those of you used to slut shaming, sex-negative terms) in a Tshirt and heels but I gotta hear that too?  so funny. we bought the condoms and got out of there pronto.

when we got back home, i made sure to let him know once again we did not need to continue if he didn’t want to. this *was* his maiden voyage post divorce and all. but he insisted this was what he wanted. tell you the truth, i was honored. and in an odd way i felt like this was really safe. we knew each other. we grew up together in that first career; goofy hang outs at happy hours, weekends with lots of mutual friends, things you do in that first job and when you’re young just out of college. kind of beautiful.

so we climbed back into bed. we start kissing again. things arise to the occasion so to speak. there in the dark, we cracked open a condom. I rolled it on to his cock and wondered if i’d done something wrong because it wouldn’t roll to the base. we kept going and when it got to the point where he penetrated me… holy… what was that?? um, wow. big. too big? whatever equipment this guy was given I didn’t due diligence before hand to gauge what I was going to be dealing with. this thing was HUGE.

he seemed to enjoy himself (i sure did) but we were both tired from the long day/ night and I was drowsy from a little too much wine so neither of us orgasmed – BUT THAT WAS FINE! we vowed to pick up where we left off in the morning.

so we wake up together. I’ve GOT to find a toothbrush – why didn’t i buy one of THOSE at CVS at 3 am?? when i got back to bed after brushing my teeth and taking a quick pee, we began kissing again. we got another condom and I unrolled it onto his cock … so THAT’s why it wouldn’t roll to the end of the shaft! He had two hands worth AND THEN SOME! ok, i’m no size queen but this was too much. he’s not a tall man so it just goes to show you, you can’t judge a book by its cover. that’s for sure. i have to admit though, it was not long (pun intended??) after penetration that i squirted. just a little. we knew it was me because he had the condom on. when the time came (too many puns) he came in a spectacular fashion; very loudly and i love it loud.

in those moments after we both were too tired to continue, he shared with me that he’d wanted to have sex with me since we were both new starts together. so you see? dreams really DO come true.  lol


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