My name is Ann and I’m 43 years old. I'm married to a wonderful man named James and I have known Jane for nearly 20 years. I am one of her few friends that know all her seedy details of her life - did you know she is a copy editor now Children’s books! I am as strait laced as you can get if you ever met me in person. I have 3 kids, 2 boys and 1 girl all under the age of 13. Been married for 20 years, work part time as receptionist and my husband is a banker, yes a banker. Jane also knows that my husband and I James have a kinky side that we keep locked away until the kids go to bed. Together we have a wonderful sex life but Jane knows that I am always willing to try new things and keep it fresh in the bedroom. Jane asked to to tell the story I told her about my first threesome.
I am no model by any means. I am about 5' 7" with long brown hair, C-cup breasts, with an pear shaped figure thanks to the kids. James is about 250 lbs. 6' 1"”with brown hair, not fat but not skinny, he would not stand out in a crowd but he keeps himself up. You however would easily accept that he is a banker by his looks. Glasses, chest hair, and no butt. He has a very average penis if not somewhat skinny.
Our closest friend in the world is Alan, we have all been friends since high school and know everything about each other. Alan and I would flirt on occasion and I would feel comfortable talking to him about all the things that I would talk to James about. Alan was the perpetual single guy for various reasons. The three of us have even been skinny dipping together, but I could have never guessed what would transpire one evening last June.
We decided to head down and spend the weekend with Alan at his cabin on the lake, he had been having a rough time at his job, as we all had been having, and we thought this weekend would be a good one to cut loose and just have fun. After spending most of the day on the lake with some light flirting I went topless for a while. Alan and James were set on being drunk for the night, and I thought I would tag along. After we got back to the cabin we wasted no time making drinks for ourselves. We sat around the table in the kitchen talking and then decided to play cards. We continued to drink playing crazy 8's and rummy 500, then James suggested that we play cards like poker. I have never played before so he had to explain it to me.
“We don't have anything to bet with I said, “You know were all broke... haha.”
“We could bet drinks, make it a drinking game.” Alan suggested.
“How about some strip poker or blackjack? My husband James chimed in. I was a bit shocked but not totally surprised since James knows Alan and I dated years ago and he knows we had sex more than 20 years ago also. James comment "It's not you have not seen her naked Alan".
Ya right! I am going to need a whole lot more of this if we decide to do that! ” I said gesturing to my nearly empty glass.
Without saying a word Alan got up out of his chair reached over and grabbed my glass with a smile. He quietly began filling my cup with another Vodka Tonic.
“I'm in.” Alan said sitting back down handing me a fresh drink. He commented back to James "Yea but that was 20 years ago James".
I could feel the warm feeling in my stomach start to grow and automatically got nervous. I couldn't believe that Alan and James wanted to do this. How could I refuse? It sounded a bit fun and the thought of seeing Alan naked intrigued me. He was a just a skinny dorky kid 20 years ago. But Alan had gorwn into a fully-fledged sexy man in the last 20 years, and with no family to tend to he had time to hit the gym every day and with a shirt off he looked good still. It was a hard to remember but it seems I also recall Alan having a sizeable tool in his pants.
If we are going to do this I would really like to lose the overhead light I suggested. Again Alan got up without a word and disappeared into the bedroom emerging with two candles, he also walked over and closed the blinds. He lit the candles and shut off all the other lights.
There, perfect he said with a smile. My husband commented "Shit Alan she's not naked yet". We played a few practice rounds and then it was time to get started for sure. James dealt the cards for black jack and I lost the first game. I discarded my shirt. Again black jack and again I lost. I discarded my undershirt revealing a white lace bra and I could feel the boy's eyes on me as I did.
You stink at this game, Alan remarked.
Shut up! I yelled with a smile. I couldn't help it, I was very aroused by the thought of their eyes on my body, but I wanted to see these two loose some clothing.
The next round that was dealt James lost and took his shirt off. The game went on until I was just in my bra and panties, my husband James was down to his underwear and socks and Alan still had his pants on. The next round was dealt and Alan lost. Off came his pants. As he took his pants down I could see his partially erect cock and it looked as every big as I recalled. James had gotten up and was getting a new drink at the time and I could not help but notice the bulge difference in each other’s underwear. Alan quipped ok ok, let's deal again I want to see her tits. The hands where dealt and I lost. I nervously stood from the table and had decided I would take my bottoms off first since I could sit back down and cover myself. I slowly rolled my white lace underwear down my legs to the floor revealing the most private part of myself to the boys at the table. I sat back down and James instinctively reached under the table and touched my leg, slowly moving up my leg, I stopped him. Not yet, I was thinking but I was somewhat nervous and horny all at the same time.
Again we continued and it was time for the boys to take their underwear off, as I won. I couldn't help but watch each of them strip down to nothing in front of me. Alan was built very different from James. Bigger, more toned, no chest hair and dirty blonde hair. He also had a nice cock, as his underwear came off his partially erect cock slipped out. Thick, long and tempting. Although we had been skinny dipping together I had never really gotten the chance to examine Alan naked, I could feel my sex tingling under the table. It wasn't long after we were all completely naked, sneaking glances of one another in the candle light.
Well, now that we are all naked what do we play for? Alan asked.
We can ask each other sex questions! ” James said, obviously excited about what was happening. Of course I lost the first game again and it was my turn to answer a question.
When you watch porn, what do you like to watch? ” James asked.
I couldn't believe he was going that in depth right away. I thought about my answer. Should I answer with something that a girl would say, or should I say what I really like?
Three-ways I answered with a confident smirk. To tell you the truth James and I had thought about doing a three way. I think that having two guys at once is so sexy. James had also asked if I could do a three way with any of his friends who would it be, and my answer was always Alan.
Three ways huh?” Alan said, again smiling at me.
Although I was drunk I could feel my face turning red. I would love to see what kind you like Alan said. He rose from the table went to his room grabbing his laptop. Here, find one you like, I want to see with a laugh he said. My husband James laughed and said "Oh this should be good." I snatched up the laptop and walked, stark naked, over to the couch in the living room. I searched for a suitable video and once I found one the boys came and joined me on the couch on either side of me. As the porno played in the background I knew that I was very wet, and I could feel the familiar pleasurable tingle that I knew well from being with James. I knew what might be happening here, but without talking to James and not being able to see his face I was unsure what was going to occur. We watched for a while laughing with Alan making snide comments.
James was filling his drink back and mine and Alan also stood up to refill his. I had avoided to much looking at Alan until now but I turned around on the couch to see both of their asses standing at the kitchen counter. Alan’s ass still looked sufficiently round for a 40 year old man. My husband James turned slightly and I could see his limp cock swinging around. Just then Alan turned around, my eyes tried t glance away but Alan was nearly fully erect. His thick long cock looked nice. Then my husband James turned and they walked back towards me.
I made some light conversation but it was only a ruse so I could see them both naked. The size difference with them both standing there was a sight to see. They both stood in front of me before sitting back down. Alan made a comment about looking at his cock. My husband James was a confident man laughed, and then commented about the size of Alan’s cock asking Alan if his dad was a horse. “How big is that thing for fuck’s sake Alan” my husband James asked. Alan quickly grabbed his cock while both of them stood in front of me. Alan answered “nine inches long, eight inches thick James”. My husband replied “That’s a big one, you like that hunny?” he asked me.
I was caught offguard for a split seacond. I don’t lie to my husband ever so I replied “Yes it looks good”. “It’s like the size of your dildo at home hunny but real”, James said. In my mind it looked every bit as big maybe bigger ad it was sexy, I only replied yes I think it is. They both sat back down Alan by now was slowly stroking his cock every so often. I felt my husband James slowly slide his hand up my leg and he didn’t stop until he had one finger inside of me as the video still played. I let out a small gasp and looked over at Alan who wasn’t watching the video anymore but staring my pussy and James fingers sliding in and out while stroking his big cock. I started to grind my hips into James hand and continuing to watch Alan stroke his cock wanting to reach over and take it from him and into my hand. Then suddenly James slid off the couch and knelt on the floor and started to go down on me.
I groaned, grabbing two handfuls of James hair and grinding my hips into him. His warm tongue felt so amazing it was hard to focus on Alan. When I leaned back I felt Alan lean into me and grab one of my breasts. His cock was fully erect and I could feel it on my leg. My husband James looked up for a moment from eating my pussy and in a very confident tone said “You said you always wanted a big cock and doesn’t every women want two men at least once!”. Yes I replied and I shoved his head back into me and told him to eat my pussy. I then took control. Alan had grabbed my hand by then I gave him a reassuring squeeze and that was all he needed.
Alan pushed the laptop off and took both of my breasts in his hands. He then leaned down and gently sucked my nipples and kissed up my chest and neck. James continued to pleasure me with his tongue, I couldn't believe how amazing having four hands on my body felt. I ran my fingers through Alan’s course hair kissing his neck and scratching my nails down his back. I pulled Alan close onto me so I could feel his smooth chest on my tits. With one hand wrapped around him and the other in James hair I nearly climaxed. Alan soon stood up legs apart over me with his hard cock in my face. My husband James till continued to eat on me and by now he had several fingers inside me at the same time.
I wrapped my hands around Alan’s cock, at that moment I could feel the difference in size as my hand did not wrap completely around his shaft and with both hands on his cock there was still more of him than my husband. I wrapped my mouth around the head of his cock stretching my jaw wider open fr him that I had to with James. I began to suck on Alan as he held my hair. I grabbed at his huge low hanging balls. It was an amazing feeling having my pussy pleasured at the same time pleasing a big cock. Soon I had my first orgasm. I help Alan’s cock tight as a came. Once the wave of that first orgasm was over my husband James stood up next to Alan. James was only partially hard so I began to suck on him until he was fully erect. I felt like an aroused queen now two cos in front of me for my pleasure. I pulled both of their cocks close to one another; you could see Alan was nearly twice the man my husband was in size.
I took turns sucking them both for a while. Alan at one point would eat on my pussy just as James had done and I could orgasm several more times. Get on your knees Alan said at one point. Without hesitation I did as he said wanting to please these two like they had just pleased me. I knelt on the floor with James and Alan standing over me. They each had their erect cock in their hands. James grabbed the back of my neck and pulled my head onto his cock. I slowly sucked at first only letting the tip enter my mouth. While I was teasing James I started to stroke Alan’s cock with my other hand. Finally I took all of James cock into my mouth and he let out a loud groan. Then I switched and I began to suck Alan. Alan said “Can you take all of me?” I tried but he was too thick and long, I pulled him out and told him he was too big for my mouth. Alan ran his fingers through my hair pulling his cock in and out of my mouth slowly at first and then he began to pick up pace. My husband stood there stroking his cock. I still couldn’t believe that my fantasy was coming true. And this side that I was seeing of Alan was so sexy it made me even more excited!
“Let’s go to the bedroom! James said.
“Yes! Alan responded out of breath has I slid him out of my mouth. Both of the boys helped me off of my knees and into the bedroom. Alan picked me up and slowly laid me down on the bed. The cool sheets felt wonderful against my bare skin. James crawled over on his hands and knees until he was over me and in between my legs. I was so wet and I wanted him inside me so badly! Even though I was so excited to have James I was wondering where Alan had disappeared to, hoping that our encounter in the living room wouldn’t be the only one, I wanted his bog cock in me bad.
“You ready babe? ” James whispered.
“Yes! ” I said without hesitation. Knowing my response to his question James plunged into me. His cock drove down deep inside me all the way to the bottom. I let out a loud groan and he thrusted in and out of me on Alan’s bed. In the midst of the familiar pleasure I had felt many times with James I began to feel Alan’s large warm hands on my smooth legs. He had retreated to get more drinks.
“Ann, tell Alan you want him James whispered. Alan it seems had told James that he would not go any farther unless I gave him the command.
“I can’t.” I said. I didn’t know if I could. I had never had sex with anyone that large I was unsure if Alan would take his time. I liked some pain but not a lot and although James believed my dildo I had used many times was the same size as Alan was bigger much bigger. I knew this my how I had held him and sucked him.
Do you want this Ann, James asked. I whispered as he fucked me that he needs to go slow at first he’s big. James leaned up and commented “You want his big cock?” “I said yes” I then told him to fuck me some more to loosen me up.
I looked over at Alan, he had one hand rubbing my leg and the other stroking his smooth large cock.
“Alan, ” I stammered, I want you now.” James pulled out of me and walked around the edge of the bed watching with wanting eyes. Alan took his place over the top of me. We made short eye contact and I slowly bit my bottom lip feeling the butterflies rage inside of my stomach. Slowly, Alan entered me. He started very gently glancing at my face to make sure that I was ok. His cock was different from James, I could feel me stretching wider and I could feel his very thick head the ridge rubbing me places James does not. The difference felt amazing. This was the type of sex that I wasn't used to. James and I would usually make passionate, hard sex. Alan was slow and steady at first, soon I asked for all of him. I gasped for air as he thrust all nine inches of thick cock in me. He did this hard only a few times and soon I orgasmed over and over. Alan drove his cock deep inside me and I felt a new sensation deep inside my pussy and with his thickness I could feel him rubbing my G-Spot with every thrust.
The orgasms felt new and different with Alan. I had never had multiple orgasms with James but Alan was delivering one Orgasm after another. Also at this time my husband James had come over my face and I was sucking his cock as Alan fucked me hard and harder.
I took my husband’s cock out of mouth, turned around as I was in doggy position and looked up into Alan’s eyes and said, “Harder! Fuck me with that big cock” I told him. Alan’s eyes lit up as his speed increased. By this time my husband was jacking off in front of me. I could no longer suck his cock with Alan fucking me so hard. Again I said, Harder! James asked me if I liked that, by now I could no longer retrain my lust, feelings or mouth. I looked up at James and said “YES! I love his fat long cock!” I turned to look at Alan and I saw a smile come over him as he continued to go faster and deeper, Alan commented “You liked this fat cock babe!”. All I could say is yes over and over.
Yes! Yes! Don’t stop! ” I could feel a new warm feeling building inside me. My husband James I would suck occasionally and he was playing with my clit by now and sucking my tits off and on. Alan was pushing me to the brink of something new, James was squeezing my tits and kissing my neck.
“Are you going to cum hard baby? James asked me. Yes! ” and as I said it I exclaimed Alan jammed his cock deep into me and I climaxed harder than I had ever before with Alan deep inside me. I shivered all over and felt my legs go limp on either side of him.
Oh, were not done with you yet!” James said with a smile.
Alan pulled out of me and flipped me over on the bed. He then grabbed my hips and plunged into me fucking me missionary style. James cock easily slid inside me since Alan’s big cock had stretched me out. The sensation of James small cock easily slipping in and out was new also. As James continued to fuck me I began to suck Alan again holding his huge cock with both my hands. I’m not how much more I could take, it seems James fucking me would get me close to orgasm again but it would not come.
James asked if I wanted Alan again and I said yes. Suddenly James stopped and walked around the edge of the bed to switch places with Alan. I gave Alan one more suck licking all the way down to his balls with my tongue. Alan then shoved his cock in me deep and began asking me if I needed it deep again. I said yes and James then took his cock and put in in my mouth.
Alan commented that I sucked cock good! James had always said that I was good at giving head, but it was so hot hearing it from someone else. I wanted to keep going, I wanted Alan to keep fucking me hard. I didn't think the night would get better. Get on top of me! ” Alan leaned over and whispered in my ear pulling out abruptly.
Without hesitation I stopped and crawled on top of Alan’s huge cock. This was my favorite position, I love to be in on top and in control and it was the position where penetration felt the deepest. I wrapped my fist around Alan’s huge cock and guided it slowly into my wet pussy. We both let out groans. I began to move hard and fast grinding my hips to meet his, I had my hands on his chest. Alan felt even deep and bigger in this position, I moaned knowing I would cum again. I knew by now the friction Alan’s huge cock made could easily make me cum. Soon I felt James behind me, his hands on my ass. I could feel his hard cock touching my ass. He positioned himself outside of my ass. I let out a groan. I couldn't believe I was going to let this happen!
This was one of my biggest fantasies coming to life. James leaned down and kissed my neck and shoulder and slowly pushed inside of my pussy as Alan slowed his thrusts. A swell of pain shot through my body. It was all so tight, and the boys could tell it was painful at first. Alan, like a gentleman, started very very slow at first waiting to see if I would be ok. Once the initial pain was gone it was unlike anything I had every felt before. Everything was so tight, so full. Soon Alan was moving at the perfect rhythm working together with James so that they were alternating going in and out of me.
This was the loudest I had been since the evening began, I had never felt such pleasure in my life. I looked down into Alan’eyes biting my lower lip. This is amazing! More Don’t stop… Yes!” Half the time I didn’t even know what I was saying. Slow and steady they fucked me.
James slid his hand up my back and neck and then grabbed a handful of my hair pulling my head to the side and kissing my neck. I could feel each ones cock, Alan’s deep inside me with James stopping short of my G-Spot. Again I felt the familiar feeling deep inside of me. It was building fast! I’m going to cum, don’t stop! I’m almost there.”
Hearing my words the boys started going faster. Alan leaned up and began to suck one of my breasts, James gave my hair another tug, and with that I exploded! I shook on top of both of their cocks spinning into the most intense orgasm of my life. I felt my body go limp and I collapsed on top of James. Alan and James then began to kiss my neck, back and chest.
Was that a good one baby? Alan asked with a smile.
Not being able to form words at the moment I just looked at him and smiled. After resting a moment I crawled back on top of Alan reverse cowgirl style. Even though my body was tired I wanted to make each of them cum the way I just did. I positioned myself up on top of James and slid his cock into my pussy very slowly. He felt amazing once I put it all of him inside me.
I gestured for my husband James to stand in front of me as I fucked Alan I leaned back and told him to cum, I then looked at James and told him the same. I was sandwiched between my two best friends feeling pleasure that I had never known. I hoisted myself up and pressed my naked body into Alan’s. James had his hands on my head fucking my mouth.
I could feel Alan’s breath deepening, breathing deep. Are you close? ” I asked him.
Yes, “Alan said. I asked him if he liked that pussy. Yes as he commented about how tight I felt, I replied I don’t get big cocks like his all the time. Tell me when Alan, I want to know when you cum!
Oh god Ann I’m coming nowhe yelled, I could feel the tip of his long cock hit my cervix! He said as he thrusted into me sharply two more times and then he popped. As Alan orgasmed my husband James pushed his cock deep inside my mouth and thrusted also, soon James pulled out and as Alan was finishing his orgasm as James would cum also pulling out of my mouth and squiring his cum my chest. Alan let his body sink down I slowly lifted up letting Alan’s still large limp cock slide out of me.
I then rolled off of Alan and, James collapsed on top of the bed. How was that love? James asked.
That was spectacular! ” I said not trying to hold back any of my excitement. I could had lost count of the orgasms and I could feel inside me the lingering sex.
James kissed me lightly on the lips and we all lay on the bed, sweaty and satisfied. We soon fell asleep together and I dreamed of the night that had just occurred wanting to wake the boys and do it all over again. It was a perfect night with people I love and I can only hope that it will happen again one day!
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