Amy's First Threesome
I had wanted to get Amy hooked up with other guys since the beginning of our relationship. I met her online, both of us in our mid to late 30's, and we got together in person a few months later. After sucking my dick (and swallowing) on the second date she was officially my girlfriend. She's about 5'4", medium long brown hair, 34 C cup, pleasantly plump with the face of a beauty queen and outgoing personality to match.
We had joked about her fooling around with other guys early on, and I made a point to nurture this bit of fun.
"He's probably going to come over here looking for a blowjob or something now", I told her in a restaurant after she had pulled her top down in jest, exposing a black lace bra and a lot of cleavage. The gesture was ostensibly for me, but there was a younger guy sitting a few booths behind us who apparently got a great look at her tits too.
She gave a big gorgeous smile and blushed.
"He wouldn't" she said softly, eyes moving to the other guy briefly.
"Trust me, he would. Want me to go ask him if he wants his dick sucked?" I asked at a very low volume.
She blushed again and her eyes darting away sheepishly told me the idea was something she was possibly not opposed to.
She was too flustered to answer so I spoke again.
"We could charge him..." I said, voice trailing up in pseudo-question fashion.
We had discussed her fantasy of being a prostitute for me several times in the past.
"How much?" she asked, regaining her composure but still with a big playful grin on her face.
"50 bucks? 75 if you swallow."
"Well you know me. I always swallow", she joked.
"I know", I answered with a grin of my own.
I often look back and wish I had set up an encounter with the young guy, but at the point the conversation lulled and we didn't pursue it.
There was a similar exchange in another fast food restaurant where there were three guys in the booth behind us, this time visible to me but not her. They all had the same construction company shirt on.
They were too close to talk about, even at low volume, so I wrote her a note.
"Those three guys behind us are checking you out. I bet they'd like to take you some place quiet and get your panties off", it said.
She straightened her hair, this time not losing composure, and wrote her response.
"You must think I'm a whore", she wrote.
I started to shake my head no when she picked up the pen and added another line.
"Wouldn't you be jealous?", she finished writing and smirked.
"Nope", I responded in text with what I hoped was a confident look on my face.
I wanted to tell her I was imagining her in a triple penetration position, with one of the men enjoying each of her three inputs. But I decided against it.
It was a trip to Portsmouth, Virginia when she finally became my swinger girlfriend. We went to see a concert and booked a hotel in the area to stay the night.
On the way out of the concert venue I turned around and noticed two younger guys looking away and smiling. To this day I think she had given them some kind of flirty look or signal but I never bothered to ask.
I was pretty buzzed, having had at least 5 large beers during the show and we smoked some pot in the parking lot beforehand to boot.
I didn't hesitate a bit in turning around and speaking to them as all of us made our way slowly to the venue exit.
"You guys wanna hook up with my girl?"
"Yeah", one of them said.
"Hell yeah", chimed in the other, excitedly.
They were kids, possibly in their late teens. I looked back at Amy and she had not turned around. I suspected she heard me, but with the noise of the crowd it's possible she didn't, and it was another thing I never asked her about.
"We're staying at the Hampton Inn, room 315. Come on by later", I told them casually, and turned around, not waiting for a response.
I put my hands back on Amy's shoulders and continued slowly guiding her to the exit.
"I think I just got you a date", I whispered in her ear after kissing her on the neck through her hair.
"What?" She asked, seeming befuddled but with a slight 'what are you talking about?' smile.
"You have a date with those two guys later", I said as quietly as I could while remaining confident that she could hear me in the throng of people walking to the exit gate.
Her eyes lit up and she flashed a gorgeous, slightly coy smile.
"I do not..." she answered.
It was a good hour later when we finally made it to the hotel. I had gotten another beer into her, as she only had 2 during the show, and we smoked another bowl in the room.
I remember pondering whether the two would show up as we heard the knock on the door.
"That may be your date, hon", I teased her.
"What?" she repeated from earlier, again with a small smile.
I opened the door to find none other than the same two young lads, eagerly eyeing the room behind me, clearly checking for Amy's presence.
"Hey, Come on in guys! I want to introduce you to Amy."
She was her normal friendly self, with no signs of resistance or concern in her demeanor as she said hello. I offered the youngters some beers and they accepted.
It wasn't too much later when I invited the two of them to trade places with me and sit with her on the loveseat.
It was getting late and they hadn't made a move so I decided to jump start things by leaving the room.
"I'm going to get us some more drinks. Help yourselves guys", I said, gesturing to Amy, wondering if I was being too obvious.
Without waiting for an answer I turned and exited. As soon as the door closed I experienced brief pangs of jealousy but quickly worked through it. There was no doubt in my mind it was what I wanted.
I went to the hotel lobby and wasted about 10 minutes before going back upstairs. When I re-entered one of them was kissing her and the other was pawing at her breasts and crotch. The image of the two of them with their hands all over her is forever burned in my memory.
"Don't mind me guys. Have at her", I said as all three of them stopped and looked up at me.
One of them looked hesitant but was reassured when the other continued his groping.
"Apparently he wants to watch", she said, turning and smiling at the guy on her left, which also helped to inspire their continued efforts.
She put her hand on his chest as he put his tongue in her mouth. The other one started fingering her pussy through her Capris pants, to which she responded by opening her legs.
The one she was kissing was apparently ready to progress things because he stood up, unbuckled his pants and produced a raging hard erection, pressing it to her lips.
Amy has always been an eager little cocksucker, and that night was no exception. She quickly leaned into his crotch and began doing her thing with typical enthusiasm as he began moaning.
Not to be outdone the other began working on removing her pants and panties, the latter of which provoked a particularly intense erection on my part. He worked with quiet efficiency, producing his own throbbing organ and seconds later inserting it into her.
He didn't last long, announcing he was going to finish and then promptly doing so. I started rubbing the front of my own pants as I watched the young buck cum into my Amy's sweet little pussy.
Taking his load bareback seemed to increase her resolve. I could tell she was applying quite a bit of suction to the other lad's cock, and he finished in her mouth shortly thereafter. As per her usual, she didn't spill a drop.
The two kids immediately began looking around and at each other as if they were ready to leave, and leave they did a few minutes later.
I wanted to tell them to stick around, and maybe drop a hint about her not being opposed to taking it in the ass, but they made for the door before I could stop them.
"You were incredible", I told her with a warm smile.
"I think they liked me", she said coyly, looking away with a grin of her own.
"I hope this won't be the last time you hook up with other guys", I said quietly into her ear as I hugged her and placed a kiss on her head.
"It definitely won't be", she confirmed softly, putting her hand on my shoulder and 'hugging me back.
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