Trying to not be an asshole [MFF] [Poly] [conflicted]

TL/DR: tempted to make a previous partner my new fuck buddy / mistress but that wouldn’t be right.

Update: Barbara just sent a nice “how are you” text this afternoon

Names changed to protect me.

After my divorce, I dated multiple people openly and discovered polyamoury (which just seemed to be a buzzword / label for what I was doing).

I had two relationships, one a woman my age who matched up on so many levels especially sexually (Anna), and one in her mid 20’s (Barbara) who was incredibly kinky, a bit more skilled and curvier (much bustier) than Anna.

Anna had no interest in threesomes, Barbara was openly bisexual. Two years ago Anna broke up with me because she didn’t want to be “one of” my girlfriends. Immediately she was who I compared anyone new I dated too, and she was even on my mind when I was with Barbara.

A month passed, and I started and ended a relationship with someone who immediately got possessive even though I was clear in dating multiple people. I began to reflect on what I wanted.

In the final discussions with Anna she explained she didn’t expect monogamy but she didn’t want her face rubbed in the fact I was dating someone else. She was okay with an open relationship / sleeping with others but wanted an emotional monogamy.

After about two months of thinking on it, I broke up with Barbara. It hurt her badly and I still felt for her but felt I was doing her a disservice constantly thinking about Anna. I tried explaining to Barbara what was my thoughts and emotional process.

Only then did I contact Anna, who 3 or 4 months later was very happy to hear from me and happier to hear I was fully single.

Sex was great, everything was great and I knew I had the freedom to date others, on the down low (as did Anna).

Several months later, swiping on Tinder, I see Barbara. I irregularly used the app, but hadn’t seen Barbara on it before. We matched chatted a bit. She no longer seemed angry or hurt and suggested we hook up for a threesome with a friend of hers.

The night arrived, I went to Barbara’s place and reacquainted myself with her friend Charlene. After a drink the girls began making out, I joined Charlene in undressing Barbara, Charlene disrobed as Barbara pounced on me, pulling down my pants. I removed my shirt as I realized I have never truly experienced cock worship before.

Both deepthroated me, Charlene was more a cheerleader though, topping Barbara, even grabbing the back of her head to force her face to fuck my cock.

I had to slow things down or I’d pop too early, I pushed Charlene back and shoved Barbara’s head between her thighs. That’s when I saw Barbara’s new buttplug. I slid two fingers into Barbara’s cunt and was furiously sloshed away in her incredibly wet pussy. I grabbed my flogger (which I hadn’t used since we broke up) from my toy bag and started flogging her as Charlene berated her between moans.

After Barbara’s ass got bright red I had Charlene suck me and put my condom on and I went behind Barbara again. I slipped in so easily and she clamped down, her kegels massaging my cock… She came with just me entering.

I could feel the plug along the top of my shaft through the thin perineum wall with each stroke. It was then that Charlene wailed loud and then growled “fuck her ass”. She got up, came around pulled the plug from Barbara’s ass. I pulled out and Charlene grabbed my cock, ripped off the condom and guided my cock to Barbara’s asshole.

They had obviously lubed before the plug because I was shaft deep in one stroke. Barbara was incoherent as Charlene had reached under to play with her clit. I had my left hand on Barbara’s hip, my right holding Charlene close when I felt Charlene push the handle of the flogger up into Barbara’s pussy. Barbara’s ass was convulsing, the braided leather handle, with the knot at it’s base adding a new texture sensation on my frenulum.

In moments I came like a geyser deep in Barbara’s ass.

Charlene gave me a hug, kissed Barbara deeply then gathered her things to leave. Barbara and I moved to the bedroom and cuddled.

She began to cry, saying she had missed me so much. That she doesn’t want to be “my dirty secret” but if that was the only way to have me, she would.

I felt so horrible. I stayed until morning, holding her and letting her cry, but I explained I couldn’t be with her like that. I didn’t tell her it’s because I still love her.

18 months later, work & family schedules (Anna has two kids and a much more demanding job) makes alone time precious. Not scarce, but we both have high sex drives. I am so tempted to text Barbara, but I know I would only end up hurting her / make her compromise herself again…

Source: reddit.com/r/Erotica/comments/asosw0/trying_to_not_be_an_asshole_mff_poly_conflicted