The first time I cheated on my girlfriend was with a work colleague who had spent months making a play for me.
I've mentioned this on a couple of stories in the past, but as a younger man I date a stunning 21yo who, unfortunately for me had a year in USA as part of her Uni course. Left back in the UK, I was completely devoted to her, but as the year passed we started to drift and contact became less frequent and often strained - this was in the late 90s and web cams/instant messaging was only in it's infancy...
Becca and I had been dating just over a year when she left for America. Initially I threw myself into work - a dead end Government job in an office full of 40-somethings and zero social life. Just after Christmas we had an influx of new recruits, most of them girls/women in their late teens and early 20s. The new people brought a new vibe and despite me supposedly saving for a trip out to the US, I started to socialise more with the new group.
There was one of the girls (Kerri) who took a shine to me - she seemed sweet and friendly. We chatted and flirted a bit during the office hours, me enjoying the attention in lieu of contact from across the pond. Kerri made it pretty obvious she was in to me, even though she knew I had a girlfriend. She invited me to her flat one Friday, which I declined because I was determined to stay faithful.
As the months rolled on, I started to get the feeling Becca maybe had something going on over there as the contact was infrequent and she showed no interest in talking about "us" and absolutely no interest in talking about sex.
One work night out we took a ferry ride across the river to a nearby town where we hit some busy bars and took in more than a few drinks. On the way across, Kerri's friend cornered me in the cabin and told me how much Kerri was in to me and that she was going to make a move that night. I told her friend that she shouldn't and that I was committed to my girlfriend, but have to admit that my cock thickened at the thought...
Kerri was a small girl, 5'3" maybe, slim, nice eyes and a lovely smile. Smallish breasts, but a great figure and she knew how to maximise her assets. Dressed in a tight fitting dress, hair up and nice eye makeup, she looked stunning that night as she smiled at me from across the cabin.
The night progressed as expected, drinks dancing and general merriment. Kerri never left my side, albeit the promised "move" never appeared. When it was time to leave and get the ferry home, I assumed she had thought better of it.
Although it was a cool spring night, I decided to stay up on deck for the short journey home. Kerri joined me a few minutes later, cuddling into me to protect herself from the cool night air. I noticed her nipples were erect through the sheer fabric of her dress and she caught my gaze as I was looking.
"You know she's having sex over there don't you?"
"What?" I stammered
"Your girlfriend. She's having sex and you shouldn't feel guilty about having some fun too"
As she spoke, she leaned in to kiss me, but I backed away...
"Kerri. I shouldn't.....you know my situation."
"You shouldn't have been looking at my nipples...but you did. Are you telling me there's nothing going on down there.....?"
As she uttered that last sentence, she lightly grabbed my crotch where my slowly thickening cock was starting to respond
Kerri leaned in again and this time I had no defenses left. Our lips met and our tongues swirled. I grabbed her round the waist and pulled her into me as we kissed deeply and passionately.
I had one hand on her bum, pushing her into me where my now rock-hard cock was pressed up against her hip.
"I told you there was something going on down there," as this previously sweet girl suddenly flashed mischief in her eyes as she parted our bodies and gently caressed my cock through my jeans.
"Kerri....oh my god, don't stop," I stammered, feeling the warmth of touch of another human being after so many months.
She dragged me to a secluded part of the deck and her hands unbuckled my belt as I fondled her breasts over her dress, feeling her rock-hard nipples that I'd gazed upon previously.
"I've wanted this in my hand for a long time," Kerri whispered as she delved her hand into my boxers and wrapped it around my throbbing cock "...and it was worth the wait," she said with a wicked smile on her face.
By now, the ferry was starting to come into dock and I knew there were only a few minutes until people would start to disembark and file past us...
Sensing this, Kerri, who had been gently and slowly jerking me, increased her pace as I moaned against her neck. My legs started to wobble as that familiar feeling started to grow, Kerri now jerking me at super speed whispered, "Cum for me, baby," in my ear.
That tipped me over the edge as I exploded all over her hand, her dress and my stomach. Rope upon rope of cum that seemed like it would never stop.
I grabbed the rail for support as she withdrew her hand and tried her best to clean up - it was a dark night, so the large wet patch on her black dress wasn't visible, but my pale blue shirt had a visible dark patch.
As people started to file past to leave the boat, we regained our composure and started to leave the boat. Kerri's friend from earlier walked by, looked me up and down and gave me a big grin as she took her friend's arm and they disappeared into the night looking for a cab.
It wasn't the last encounter we had, it turned out she had been right about my girlfriend all along...
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