Jen and Brian – The Early Years.
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The Threesome
While soaking in a hotel hot tub a women joined us, this short story is not exactly erotic but it relates to the next short story. We struck up a conversation as we were the only three people in the spa pool area.
We were maybe a month into dating, a young couple in our late twenties. Her name, the other guest, was Wanda she was in her forties and looked good in her one piece swimsuit. We learned she was a business owner and was in town on a business trip. She was the mother of two teen adults and divorced several years. Wanda thanked us for sharing the hot tub and told us, two young people should be alone in a tub. I remember she kept eye contact with both of us the whole time, it seemed a little intense. As she was leaving she let us know her room number and invited us to visit her later in her room for drinks and “fun”.
Jen and I were still getting to know each other so we laughed, ‘Did that just happen?’ ‘Did she just invite us for sex?’ We did not take her up on her offer but months later we both agreed if a similar opportunity presented itself again we may not pass it up.
Several months later and I sort of created an opportunity. I used to work with my best bud Ernie, I actually got him the job but we worked different shifts in a public setting, and Jen would see me and Ernie around shift changes. Jen would talk to both of us, Ernie and Jen went out for drinks twice and I later learned ‘made-out’ once for a little bit but never had sex. Skip ahead a year
and me and Jen were engaged and the wedding was a couple months away. Before we tied the knot I got it in my head I wanted to see Jen fucked by another guy. I brought this up to Jen and suggested Ernie since he is going to be my best man anyway, Jen said she was curious and that she would have probably fucked him if we had not started dating.
I talked to Ernie, he was reluctant at first because we were buddies and not gay. I let him know it was alright, that Jen was interested in hooking up with both of us at the same time, that I was curious and cool with it too. I picked Ernie up in the evening and we went over to Jen’s place.
We put on a comedy movie and had some drinks and snacks and all sat on the couch with Jen in the middle, and nothing was happening, I guess we were waiting for someone to make the first move.
The movie ended and Ernie said, “I guess I should get home.”
I was thinking to myself no this has to happen so I took Jen’s hand and put it on Ernie’s bulge and squeezed her hand… Jen let her hand stay and continued to squeeze his dick through his shorts, it did not take much for him to get hard. “Since you guys have kissed before maybe you should start making out,” I suggested, I took on the roll of directing our little orgy my next suggestion was to start undressing and off went the shirts.
We were all bare chested and Jen’s tits became a focal point as they continued to kiss and touch, I was caressing Jen all over too.
I told Jen, “Get Ernie’s dick out and play with it,” she reached into his shorts and took hold of his shaft. Ernie pulled the shorts down and kicked them off, I stripped and because Jen was sitting in the middle of us she started slowly pumping both our cock’s at the same time.
Ernie and I have seen each other naked in the showers of our local gym, but never hard and turned on like we were now. Ernie had an inch on me but I made up for that with a larger girth. Jen turned toward Ernie and with her left hand took hold of Ernie’s balls and began to suck his cock while she reached back with her right hand and continued to pump on me alternating between my cock and balls. It was so hot watching Jen suck Ernie’s dick and see pleasure on his face. I reached over and placed my hand on her head so I could feel the up and down motion of her sucking.
I tossed some blankets and pillows on the floor in front of the couch.
“Lay down,” I asked Jen. Back then Jen was sporting a runway of hair above her slit but shaved on the sides and all the way down. I watched Ernie move to the floor and kneel between her legs, he got busy eating her out licking, sucking, and fingering her wet pussy, watching him pleasure Jen was such a turn on. I gave him a squirt of lube to rub all over his cock and Jen bent her
legs up as Ernie rubbed his dick up and down her slit then I watched his dick disappear into her pussy.
I moved behind Ernie and watched his balls hit her ass as he fucked her. I was pulling on my dick this whole time and I moved up by Jen’s shoulders, she took a hold of my cock again as I moved close enough for her to start sucking the head of my dick.
I was moving my hands all over Jen’s body, I placed my hand on her mound and could feel Ernie’s dick moving inside her as she had her first orgasm. Jen was on the pill so no rubbers tonight, Ernie was ready to cum and pulled out and shot his load on her belly, that was the first and only time I had seen another guy cum in person, I probably could have shot my load in Jen’s mouth but I wanted Ernie to watch me fuck Jenny as I had watched him.
I moved over and slid my meat into her very wet pussy and began my turn fucking Jen, Ernie kneeled next to us and Jen played with his wilting man hood. I told Ernie to feel her mound like I did so he could feel me moving in and out of her. After a while Ernie moved his fingers to either side of her pussy lips while I was fucking her and I could feel his fingers touch my shaft as I slid in and out, maybe I imagined it, but the slight touch of his fingers seemed warmer than Jen’s pussy.
Jen gasped, “OHH,” as she rode out her second orgasm.
I was there too and pulled out to shoot my load with Ernie’s on Jen’s belly, not sure if it was the excitement of this new experience but I shot way more cum than Ernie did, it mixed with his drying cum on her belly and was running down her side. Jen disappeared to clean up the mess we made on her.
We got dressed and both agreed that was amazing, we both gave Jen a kiss and I took Ernie home.
Funny side story, Ernie’s then ‘not so serious’ girlfriend called his flip phone and told him she needed to be fucked, if he said no he might not get another chance. We stopped by my place so he could take a quick shower, she met him at his house when I dropped him off. Ernie told later with a wink that she was impressed he lasted so long that night.
The Camp Site
Jen and myself discovered the thrill of public sex by chance. We were camping, I’d been camping most of my life, Jen not so much. We were set up in tents in an open area, in a part of the town around a monument type lighthouse. There were hundreds of others around us, tents just a few feet away on all sides.
Jen and I had only been dating for a few months and were fucking every chance we got. The night was late and we crawled into our tent and fell asleep pretty quick.
We both woke up a little later, there were people up all hours of the night just chatting and sitting around fire-pit fires, of course I woke up with an erection and spooned myself up against Jen, she reached back and started to rub my cock through my shorts. I reciprocated by putting my hands on her breast and mound.
Jen was wearing a long t-shirt and panties. She turned around and began kissing me and touching herself, I loved watching her masturbate while I stroked my cock, we were whispering our pleasure noises. I repositioned myself, Jen was on her back, I moved on my side her legs draped over my hips we formed a T shape my upper torso facing her right side and my legs and feet facing her left, this let me enter her pussy and watch her play with her tits and pussy while I fucked her, it was very dark and people were moving around the tents it was exciting and we were both quick to cum.
The Doctors Office
Some of our sexual adventures were spontaneous and some planned, another quickie was in my doctors exam room. We were married by then and Jen went with me to my appointment.
This doctor has a history of keeping patients waiting, thirty or forty minutes was common, after my vitals were taken we settled in for the wait. I noticed Jen was wearing her jean skirt, I could see her panties and that made me hard. I was wearing a t-shirt, shorts and flip-flops and Jen noticed my tenting cock, she was a little embarrassed that the doctor would see and suggested I should quickly jack it off.
I pulled it out and stood in front of her face and started masturbating. It did not take long and Jen had her mouth on my cock helping to excite me. I told her to take her panties off and sit on the exam table as it was just the right height to get my cock in her while she sat on the edge with her legs slightly spread. I shot my load in her just in time as the doctor showed up five minutes later.
The Ferris Wheel Fuck
We planned the ‘Ferris Wheel Fuck’ in Chicago, it was a huge Wheel where they load two baskets at a time and you end up at the top, stopped for a minute. When we were a couple baskets up we started rubbing on each other. Jen was wearing a short dress and had taken her panties off before we got on the Wheel. When we stopped about two baskets from the top Jen started sucking my cock and when we were stopped directly on the top of the wheel she moved over and sat on my lap allowing me to enter her love hole.
I was able to fuck her for a couple of minutes before we moved down a couple of cars. Jen covertly kept her hands on my dick, when the wheel was full and we started our continuous ride I started to whack on my cock while I watched
Jen finger herself, just before I shot my load, I let Jen know and she bent down and took my load in her mouth, as we needed to keep it clean for the next rider.
Storm sex
This adventure was a long time in the planning, at least 5 years since I got the idea. It was only fourteen months before Jen died that we pulled it off, a lot of circumstances had to converge for my plan to work.
I wanted to fuck Jen during a thunder and lightning storm, it’s all about the adrenaline rush and heightened senses while fucking.
So we have a hot July evening -check, we have a thunder storm warning -check, we have the twins at summer camp -check, we have backyard privacy -check, we have a ground cloth and a patio couch cushion at the ready -check. Quick run for some grocery store flowers and Jen’s favorite candy and of course, a big glass of wine, now I just had to get the wife on board.
“Hey babe it’s going storm soon and we have the house to ourselves.”
….”What?”…
“You know? Screwing out in a storm.”
“Are you serious, are you still thinking about that crazy stunt?”
“Yeah babe, look I got you some flowers and your favorite candy, here have some more wine babe.”
“Brian, you know I don’t like storms, what if we get struck by fucking lightning?”
“Well that’s one way to get on the TV show ‘Stupid Ways to Die,’ come on I think it’s going to happen tonight, It’s warm and were alone.”
“Ok, maybe, but if I fall asleep don’t be waking me up at 2am.”
“Ok babe how’s your candy?”
There was a thunder clap and the rain fell. I really wanted Jen to enjoy this experience like she did the many others. I was rubbing her neck and shoulders and giving her little kisses on the same, this always got her in the mood.
I took my time, I was pretty good at neck and back rubs, after all, I have twenty years experience with the same and only woman. I unbuttoned her blouse and helped her undress, I was naked too. Jen was laying face down on our futon and I was giving her the full massage treatment while letting her feel my hard meat rub against her butt crack.
The rain was pouring now and the thunder was getting closer.
I asked Jen, “Are you ready?” I did my job of getting her relaxed and turned on. It was dark and the rain felt cool but the summer heat made it comfortable.
I put the cushion down on the tarp and Jen kneeled down and took my cock in her mouth, her hair was soaked by now and I moved it off her face. I watched the rain drizzle down her face as her mouth moved over my cock, she concentrated on my dick head while tugging on my balls, it was sooo good, sooo hot to watch.
There was a flash of lightning and clap of thunder. Jen paused her sucking and I knelt down with her and kissed her passionately our tongues lashing around the rain water mixing in our mouths. Jen’s nipples were rock hard, I needed to suck them and flick them with my tongue. Another flash of lightning and clap of thunder, Jen jumped, she laid back and I moved my mouth down to her mound and pussy lips, Jen was shivering a little but not with cold, she was frightened.
I stopped my licking of her cunt and moved up to her ear and asked, “Do you want to stop?”
Jen told me no that she wanted me to have my fantasy and to hurry and fuck her now. I slid my meat into her and fucked her hard and fast my senses were raw with exhilaration. The wind was swirling furiously now and as I continued my penetration of Jen I heard a tree branch crack and fall nearby.
Jen begged me to fuck her harder. So much rain had fallen that our little ground mat was flooded with a couple inches of rain, we were so wet our bodies were slippery against each other, Jen cried “Oh my God, I’m cumming so hard.”
I continued my furious hammering of her pussy and shot my load deep in her and grunted “Oh baby – Oh baby,” with each contraction of my cock. I collapsed on her and we lay in a heap, breathing heavy letting the rain wash away the cum running from her fuck hole. We had plenty of sex after that but that was our last great adventure.