There’s been very little playing in my life lately and I can’t believe it’s taken this long for something to happen that I feel is worth writing about.
I’ve been to only one swinger’s party with my husband in a month and a half. We’ve done normal vanilla stuff, which is fine, but I haven't even been in the mood for that and, on top of it all, the Covid vaccine kicked my ass.
Just when I thought it couldn't get worse, I heard from Jackie. She’s featured in a few of my journal entries and she’s had coitus with my husband on and off for over a decade. She’s fun and I really like her. So, when I got a text saying she needed a favor, I waited until we were both out of work.
I know she’s having marital problems — it’s been going on as long as I’ve known her. Ryan is a cool guy but I hope I don't have sex with him again. Not that he’s bad — he's just not that good!
But Jackie’s favor didn’t involve Ryan. She asked me to be her wing girl at a gangbang she’d set up through a lifestyle guy we know named Ed. I said I wasn’t in the mood but she assured me I didn't have to have sex. She needed somebody to make her feel safe. We’ve done it before and it always ended well but I said my guy wouldn't let me.
“Let me handle that,” she said.
When I got home, hubby asked, “So Jackie needs a wing girl again huh?”
“Yes, but I don't really wanna go.”
“You should go. She needs a friend to watch out for her and, who knows, you may get lucky, too.”
“You'd let me play?” I asked.
Hubby said he’d noticed my recent misery and maybe this was my chance to have some fun. I said I’d talk to Jackie and think about it.
She’d arranged it for Monday at a hotel just south of Boston and I was talked into when she said, “It’s only four guys and I really need it.”
After a long boring weekend, I texted Jackie that I’d got my period. It wasn't true but I didn't want her or the guys thinking I could be persuaded to play. She seemed bummed but understood and as I pulled into the parking lot at 7pm I got two texts. The first was from my guy. ‘Have fun if you want and make sure Jackie is safe.’ The second message was from Jackie: ‘Room 416.’
I walked past the reception desk to the elevator with that guilty feeling of eyes on me. It was silent and the place seemed empty… until I got to 416.
Jackie was there with Ed and another guy and I said I needed a drink. The wine wasn't that good but I’d got my first glass down when two more guys showed up. “Waiting on one more,” Jackie said.
I knew two of them — Ed and Rob, who was kind of creepy but well hung. He always wore swishy pants and paid for laser hair removal everywhere. The guys couldn't wait so they disrobed and I guess Jackie had warned them that I had my period. The average penis size looked around seven inches, maybe bigger.
Jackie is a champ. I watched her handle her business in all three holes for about twenty minutes before there was a knock on the door. I was told, “That’s Blake,” and I went to the door and looked through the peephole at a guy standing in the corridor.
I opened the door and said, “Blake?”
“Yes. Lindsay, right?”
“How did you know?” I asked as he walked in and grabbed a beer.
Blake apologized for being late, saying he’d come right from work. “Are you playing?” he asked.
“No. My period came today.”
“Damn,” he said. “I’ve been dreaming of it with you for a year or so.”
“You don't know me,” I said.
“I’ve been to ESC and on both websites you’re on. I’ve seen you and I think you’re beautiful.”
I thanked him. “Maybe another time.”
He went to the bathroom, turned on the shower, disrobed, and got in. Curious, I looked in and saw his perfect body and large fat cock. Yes, he was good-looking and hung like a thermos — so, he was definitely my type. But, no, I wasn’t playing.
Jackie got them all to cum but Blake really pounded her, just the way I like. I watched his cock go in every hole Jackie had and she seemed so happy. He asked me, “Are you sure?” and I told him I was sure, no playing for me tonight.
He said he hated when too many people were watching; it made him self-conscious and he couldn’t perform the way he wanted.
“Oh sure, Blake,” I grinned, “whatever you gotta tell yourself.”
Each guy gradually dropped out. Jackie seemed happy after getting up for water breaks and not being sore dealing with Viagra men. The pair that arrived together left first.
Blake finally filled his condom and was all sweaty and glistening. Jackie kissed him and I was a little jealous but he went for another shower while I sat with her. She hugged me, thanked me for being there, and said that she really needed the session. I noticed it had been just over an hour — I prefer longer!
I talked to Ed while he dressed and I heard Blake call out, “Is there any chance one of you is going North of Boston? It’d help if didn't have to take a uber or the subway.”
Ed was local and Jackie said, “Sorry, south shore here — but Lindsay is North.”
I asked Blake, “Where ya going?”
“Revere.”
It’s a city I drive through to get home so I agreed to give him a ride. After we all said our goodbyes, Blake walked to my car and told me exactly where he lived and we chatted and laughed on the way. He was cute and I asked how old he was — and he was three years older than I imagined.
I asked if he smoked weed and I pulled out a joint. “But I don’t smoke in my car,” I said.
He said we could smoke in his driveway. I was impressed that he lived on the beach and not in the gross city. He’d moved in a few months ago and, after I’d parked and we’d smoked, he said, “You might as well come up to my place.”
We took the stairs up one floor and his home was clean and I complimented him on it. He said he'd dreamed of having me in his place.
“Oh, really, why?”
“I’ve chatted with you on AFF and I always masturbate.”
“Oh my god,” I said. “I know you now.”
By now, we were stoned and he offered me a drink of bourbon. We clinked glasses and he said, “I need another favor. May I kiss you goodnight?”
The fact that he’d asked, made me somewhat horny — and he was a great kisser. He looked me in the eyes, held me tight, and said, “God you’re so beautiful,” and squeezed my ass while kissing me again.
It was enough to make me whimper and I pulled back from the kiss and said, “Blake, I lied.”
“About what?”
“I don't have my period.”
He stared at me, then picked me up and kissed me all the way to his bed. I straddled him and we made out like teenagers, undressing each other. We locked in a sixty-nine and my jaw ached to suck his cock. I hoped it would still taste of Jackie but, of course, it was clean from his shower.
I moaned as he did a great job licking and fingering me. He pushed me off, sat on my chest, and said, “I know you like this,” and fed me his cock. He told me I was beautiful before raising my legs high and driving inside me.
“You’re on Viagra, aren’t you?” I said.
“Yes, I am,” he admitted and really fucked me harder and faster than he did with Jackie.
I wanted him to last longer but he pulled out and came all over my stomach and tits. It felt so good to cum and make somebody cum like that. It was just what I needed and he hoped we would play again. I took his phone and put my number in it.
On the drive home, I blasted loud music as I was still stoned. I told my husband what'd happened. “I played for ten minutes with someone good,” I said, “but the ending was too fast.”
He laughed and after I showered, we made love while I thought of Blake. I wanted to be fucked not made love to. Well, let’s see how I feel in the morning…