Page 16 of Festive Flings

~ Tim ~

I set Jamie up with an old friend of mine called Conor. He reminds me he isn’t looking for anything serious, but I don’t think Jamie will mind. We have reservations at the Italian Kitchen in Oxford Circus, and with our window table, we should be able to see the big reveal when the Christmas lights are officially switched on.

Jamie’s friend Iris is nice enough. She is medium height with brown hair that falls in waves down her back, and she has a very slim and slight figure. She isn’t my usual type, but she seems likeable. I am looking forward to seeing Jamie and Conor together and therefore, one date with Iris will be okay.

Jamie seems excited until we approach the restaurant and her nerves kick in.

“Tim, what was I thinking? I can't do this! I am a wreck. What if he doesn’t show up or he doesn’t like me? What will I talk about?” I drag her into the restaurant before she can change her mind. Thankfully, Conor is already inside waiting for us.

“You must be Jamie? Tim has told me a lot about you. What can I get you to drink?” Conor is charming. I watch as Jamie relaxes in his company, and I take pleasure in knowing I am helping Jamie move on from her dickhead ex, Carl.

This isn’t going to be some big love affair. I can tell the chemistry isn’t there between them, but this date serves to boost Jamie’s confidence in dating. If they can have a bit of fun in the process, all the better.

We share a bottle of wine, and the banter between the four of us is brilliant. When the Christmas lights are officially switched on outside, we cheer. After we have finished eating, we walk hand in hand with our dates, soaking in the festive atmosphere and cheer.

“Come back to mine,” Iris persuades me, looking at me seductively through her eyelashes and wetting her lips with her tongue. It is an open invitation for extra fun, and so we say goodnight to Jamie and Conor and head back to her place.

As I walk into her apartment, she presses her lithe body into mine, her dress is off in one swift movement and by the time we have our first proper kiss she is already naked. Within minutes she is on her knees in front of me, she frantically whips my cock out of my jeans and slowly wraps her tongue around my hard head. I groan in appreciation as she licks all the way down to the base and then all the way back up before taking me fully into her mouth. She works wonders with her tongue, her warm mouth is inviting and sends tingles of satisfaction right down into my balls, which she is now grabbing and holding.

“Slow down, sweetheart, or I’m gonna cum right down your throat,” I warn her, but that seems to encourage her all the more and after a couple more minutes, I shoot my hot load. However, to my great shame, something weird happens in those moments just before I do. Her face seems so clear in front of my eyes, but it isn’t Iris’ face.

It is Lauren’s.

It freaks me out a bit, but I feel bad running out on Iris after she has just given me a pretty decent blow job, so I stay and reciprocate. As I run my hands over her thin body, I don’t feel desire. Not like I did for Lauren. Iris’ bony hips and skinny legs leave me scared in case I break her. I long for the soft, plump body I know Lauren had hidden under the clothes she didn’t remove.

My thoughts about Lauren fill me with guilt about Iris, who is lying next to me. I want her to feel good and satisfied, and so I fuck her with my fingers, bringing her to orgasm before thanking her for a lovely time and leaving.

I walk a couple of miles to try and clear my head. I really like Lauren. I know she isn’t the conventional ‘pretty girl’ but to me, she is perfect. It is frustrating and confusing that she seems to be avoiding me. She was so unsure of herself and vulnerable that night we kissed and part of me just wants to go and knock on her door and tell her how I feel. Knowing that I sound weird and overbearing, I stay away and hope with all my might that she will eventually agree to see me again.

Until then, I think I’m best keeping my cock to myself.

~ Jamie ~

After Iris and Tim leave, Conor invites me back to his place. At first, I am a little unsure. I have never had a one night stand before and I don’t envision anything more than tonight happening with Conor. He is nice enough, but the spark isn’t there between us.

“Come to mine, we can have a bit of mutual fun, nothing heavy. It's been such a good night, I can't think of a better way to end it.”

So, with anticipation building up inside my body, I agree. A bit of fun is what I have been looking for, and no-strings-attached sounds like a good option.

“Okay, I’ll come back with you. But look, I don’t do this kind of thing; I’m not really sure what I am doing.” He takes hold of my hand and tells me to relax and to trust him and that he will take care of me.

Carl and I had quite an active sex life until that last year, so I am not a shrinking violet, but he is still the only person who has carnal knowledge of me. I hate that he is the only man I have ever been with.

The prospect of sharing someone else’s bed is scary, but I have been feeling horny and unsatisfied, and Conor seems to know what he is doing. I am hopeful that he can satisfy the itch that has been bugging me.

As we walk along Oxford Road, we kiss until we manage to flag a taxi. Heading back to his house, things quickly get hot and heavy between us.

Heat rises within me, and the ache between my legs begins to burn and grow. Conor is a decent kisser, and as we trundle along in the taxi he deftly slips his hand up my skirt and into the side of my panties.

“I know you want this, Jamie; I can feel how hot and ready you are. What do you like?” I do want this, and the more he teases me, the more I want him.

The taxi pulls up outside a new development and Conor quickly pays. He shows me to his second-floor apartment, which is on the small side but modern and tidy.

He pulls me into his bedroom, and we undress each other in between hot kisses. I am so tightly wound up now that it wouldn’t normally take me long to cum, but we don’t seem to hit a good rhythm between us. Conor is decent enough, but the sex is off-kilter, unfamiliar and awkward.

I don’t cum, but he does. And once he does, he thanks me for a good time and kisses me goodnight.

Once my Uber turns up, I let myself out of his apartment. Feeling cheap and deflated, I consider my evening. Although I don’t regret what I did, this night has confirmed to me that I am not that sort of girl. One night stands are not for me. I have got that out of my system and I will no longer wonder what that would be like.

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