MILF Meets the Roofers

It's a long ride on your way to your first threesome.  No matter if you are driving 2 hours or 2 minutes, it seems like you are forever getting there.

You don't know if the thoughts in your mind or the blood in your cock will explode first.
 
You have nothing to go on but a few grainy photos; usually one, maybe two if you are lucky.  And the eyes... the eyes are always blotted out in those photos. No one wants to be recognized by friends or family.  They never realize that friends or family would have to be swinging to see those grainy photos in the swinger magazines.  Those "dirty" magazines hidden in the back of the combination book store/record shop.
 
Yes, you were nervous going to the checkout with those swinger mags, purchasing some mediocre cd or magazine to hide from the other patrons the depravity of the sex acts dominating your thoughts.  The relief you feel when you are sitting in your car with your treasure.  The thrill of looking through the candidates, sifting through the obese or obnoxious looking couples to find that perfect gem, the one couple that displays "couple or single male wanted."  You don't focus on the husbands, just the wives to see if they are hot.  Hell, they don't have to be hot, just the average to middling females who aren't looking for 10 inch cocks.  They nearly all ask for 10 inch cocks for a 7 inch cock holster.  You curse your parents for the mediocrity of your birth right.
 
You find a few candidates. You mail to the reference number on the photo c/o the magazine forwarding service, enclose your Polaroids....and wait.  You buy an answering machine...and wait.  You check your messages for two weeks...and wait.  You wait and you masturbate to the thoughts of what you want to happen.  The answer doesn't come by phone, but by mail.  The couple writes and expresses interest.  Apparently your cock pick wasn't all that mediocre, or it's your young flesh she desires more than the cervix pounding from the other bullish candidates.  
 
They send photos. Colored ones. Kodachrome.
 
They give you a phone number. A city two hours away. They are a better than average couple.  No heavy weights. He is bi, she is straight. Your are 24.  They are 33 and 35.  You haven't tried bisexuality before, but your heart is racing now, anticipating something new, something erotic...your first threesome.
 
You call the number. The wife answers and you give them the phony last name that you made up on the letter, and they give you the phony last name that they made up.  It's part of the game.   You banter nervously. They ask questions. You ask questions.  "What do you enjoy?"  "Do you like anal?"  "Do you like cum in your mouth?"  It doesn't matter.  If they said that they were going to cut your throat afterward, you would still go.  You are hooked. You set up a weekend meet at a motel at their location. King-size bed. Hard to explain to the motel clerk why you are asking for a king-size bed.  They don't ask. They've seen it all.
 
The husband picks you up at the motel. Nice guy. Personable. Not his first rodeo. He drives you to their place, which is a surprise, but you are so nervous that you don't remember the address or how to get there. You go in. You meet the wife and son. She doesn't disappoint.  She is a looker. The teenage son is off to a friend's place and you are just someone going to a party with his parents. He doesn't know that you will be soon fucking his mother.  After the son leaves, they show you photos of their past swinging adventures.  If you had doubts, then now you are sure that this isn't their first rodeo.  Your cock or your mind. Both are about to explode.
 
They follow you back to the hotel room that you rented.  Locked door, "Do not Disturb" sign.
 
She kisses her husband and it starts. The disrobing. You are nervous. What to do first. Follow their lead and try not to appear overbearing or demanding.  She's on the bed, and he dives into a mouthful of vaginal bliss. You nervously start kissing her, massaging her breast, kissing her nipples.  Then you get on your knees and present your mediocre cock for her to devour.  She doesn't hesitate.  She has your cock buried down her throat while the husband buries his tongue in her bush.  The husband comes up for air, and moves to her breast, teasing.  You move to the holy of holies.  You lick, suck, and drink in the juices, probing with deep tongue thrusts, tasting the walls of her vaginal cavity while she is licking the husband's cock. Your member is not much different than his. You are relieved.  
 
The position changes. She lays on her side. He enters her vagina from the rear, leaving her clitoris exposed. She discussed this with you on the phone.  Licking her while her husband fucks.  You go down and start to lick that clitoris, less than a inch from the pounding cock. You remember that he is bi. He wants this. You hesitantly reach up, and start to cradle his jewels, all the time her juices mingles with the fleshy taste of cock.  You can't bring yourself to put his cock in your mouth, so you go on licking the clit and fondling the balls until he grunts and fills her with cum.  He withdraws. You switch position.  His cum lubricates her vagina.  There is nothing sloppy about these seconds. You pound her while he licks and returns the favor of cradling your balls.  He doesn't suck you off, not sure if you will be offended. It doesn't matter he says. They just love fucking.  
 
You release your semen into her, and you all relax, sitting and talking while a double load of cum streams from her pussy. You regret what the hotel maids will have to clean up. She pees. Returns. The ritual starts again. This time the cunnilingus is mixed with unfamiliar flavors. His cum. Your cum.  You don't give a fuck.  The thrill of the three-way has over ridden any social mores that you were raised with.
 
More sex. More bi touching. This time you pull out and shoot your cum over her.  With that baptism, the holy rites have been completed. There are photos and kisses given. Promises of future sex.
 
This was your first threesome.

Like many people, I was really mad, confused, upset and various other emotions after my divorce from first husband. He cheated often. Constantly saying it would never happen again, and of course it did. Then we separated for a bit. Once we got back together he said it wouldn't happen again. At this point he talked me into swapping a couple of times. I went along with it thinking it would help the marriage, of course it didn't. And I soon found out that he was once again screwing his secretary. So I knew divorce was looming so I went out and a brief affair with a married coworker of mine. To be honest he was a nice guy and I felt bad being the other woman. I felt really guilty one time we were on a business trip together, we had been in meetings all day and were back in his room and had a drink or two. I had removed my blouse and he had removed his pants and I was on my knees giving him oral when the room phone rang (cell phones not that common back then). It was his wife....for some reason I felt sorry for her. The affair soon ended after that. 
 
Fast forward a few months, my divorce is final and I had just moved into a apartment. Across the street from the apartment was a shopping center which was handy, because there was a grocery store there and a dry cleaners that I would use.
 
After a couple of long weeks at work (I had attended back to back conferences) I had a weekend to myself. I had made no plans because I just wanted to rest up after the road trips.
 
Saturday afternoon I decide to walk over and grab some things at the store. While walking down one of the aisles a man comes walking towards me. We just smile at each other, no words spoken. Well it was at that point things startled to tingle. I was now horny and realized I had made no plans to go out Saturday night or Sunday. So now I'm feeling bored and horny.
 
As I'm walking out of the store, I noticed the guy I smiled at getting into what looked to be his work van. Not sure what came over me (maybe the new sense of self-empowerment after the divorce), I simply walked up to his van and motioned for him to roll down the window. I simply smiled and said, "Not sure if you are busy with work, but if you have time for a quick fuck I live in apartment 212 right across the street". Didn't wait for a reply, simply turned and walked towards my apartment.
 
Needles to say my heart was beating a bit fast as I walked across the street and up the stairs to my apartment. I went into the kitchen and put the few things I bought away...and then heard a knock on the door. Now my heart rate skyrocketed.  I opened the door and said something like, "I'm glad you had some time to spare." I barely gotten the words out when he had grabbed me and pulled me close to him and next thing I know our tongues are entangled and our hands are exploring each other's bodies.
 
Once the door closed I thought we would head to the bedroom but I guess we were both so hot and horny we ended up fucking right there on the living room floor. Never made to the couch let along the bedroom. Clothes were off in a matter of seconds. We barely said a word to each other the entire time he was there....which I guess was 45 minutes or so, it seemed to go by so quickly. I was wet the moment he touched me and he went down on me instantly. Now he didn't go down for a quick lick and then expect a blowjob he stayed down there until I came, and I came hard. I returned the favor and went down on him....he fucked me from behind, me on top of him and missionary. I knew I came at least one more time. I'm sure he came but I just remember him being hard all the time lol.
 
After my second orgasm I was out of breath and thought I was about to pass out. At that point he got up and said he had appointment he had to get to. He dressed and left, I was still nude, sweaty and hot and just laid on the floor for another half hour trying to put my thoughts together on what happened. I tried not to over analyze it, just took it for what it was. A great fuck session with a guy I never saw again.
 

Sue and I both decided to take the part-time jobs as there were only two months left in the semester.  For the next eight Saturdays I bussed tables while she waited on tables in short shorts and an apron from the waist down.  It was an incredible experience that would make me hard watching the number of guys that got to see her 34C tits and light-colored nipples.  And that would last for 4 hours every Saturday. 
 
As we were coming to our last Saturday of the semester and subsequent return to our home state I thought it would be cool to let the guys of our dorm know about the job she had had the previous two months.  Initially some of them were in disbelief but didn't want to miss out on seeing her tits as many had probably imagined what they looked like since she was primarily braless during the semester. 
 
On the way to work on her final Saturday I told her to expect some surprise visitors.  She gave me that look of "now what did you do?" and I told her.  After some make believe "I can't believe you did that!" she settled in with the realization that she would be seeing a number of guys she had gotten to know, and more importantly, they would now actually see her naked breasts for the first time. 
 
Sure enough about 12 guys from the dorm came in, a few of which were friends and not even from our dorm.  After the initial uncomfortableness she became totally at ease with the situation and didn't mind the outright staring at her boobs. 
 
Little did I know what this would evolve into, until our following Junior school year as we went on another student exchange program to a school in northern California.  Sue and I ended up in different dorms but I had become friends with Dan who lived on the floor above me.  He was a senior and had a single room.  The three of us were listening to music and just visiting in his room one night and Dan dropped a deck of cards on a table and asked, "Want to play cards?"  He and I had preplanned this and I responded with, "All I know how to play is poker."  Sue replied she knew Crazy 8's.  Dan said, "I dare you guys to play strip poker."  Sue looked at me and said, "Be honest with me - you guys have already talked about this, haven't you?"  I replied, "Honestly, yes - how'd you know?"  She just shook her head and said, "Who is dealing first?"  I immediately started getting hard and Sue gave me this look that I didn't quite understand.
 
Eventually we were all down to our underwear with Sue having a bra on (for some reason) and panties.  She then lost a hand and as she stood up to unclasp her bra from the front I told her to stop.  Sue asked "why?" to which Dan replied with a laugh "yeah, why?".  I then said that part of the game at this point is that the guys got to take her bra off as slow as we wanted.  I'm guessing the beer we had been drinking had something to do with it but Sue willingly smiled and said "guys are perverts" and put her hands to her sides. 
 
Dan and I each took one side of the clasp in the front of her bra and slowly unhooked it and dragged our hands across each tit.  Sue was now letting Dan feel her up and was actually getting into it.  After about 15 seconds or so she said that was enough and time to deal another hand. 
 
So the three of us were now all sitting on the bed with Dan and I having obvious hard-on's and Sue's nipples were erect.  The next hand Sue also lost and as she stood up, Dan and I also stood up and said, "We get to take these off."  I asked Dan, "Do you want the front or the back?" (knowing full well he would take the front). 
 
As we pulled her panties down, Dan slowly ran his middle finger down the slit of Sue's cunt, and then right back up it.  She said that was enough, but that it was our turn to lose our underwear to end the game.  We told her the game was over as she had lost all her clothes.  She jokingly said that it wasn't fair.  I then said, "I tell you what, we'll play one more hand and if you win, we'll take our underwear off, but if you lose the hand since you're already naked, you have to lie down on the bed and Dan and I can use our hands only on you." 
 
She didn't fight that idea at all and simply said, "For how long?"  I said, "We'll draw a card from the deck and whatever the card is it would be for that amount of time in minutes, face cards would be ten minutes, Aces would be 15 minutes,  but the Queen of Spades would be an hour." I has said the last one as I envisioned that card looking a little like her pussy. 
 
Unfortunately the card she picked from the deck was a 6 so for the next six minutes Dan and I were feeling her tits and pussy.  Dan tried to insert his finger in her cunt and she said that wasn't part of the game.  With that the night ended and Sue and I went back to our respective rooms.  The next day when I saw Sue I told her I had trouble sleeping as I kept thinking about what had happened.  She admitted the same thing and said she was surprised at how  much it turned her on as she was thinking about it in bed.  I had been worried a little bit that she was going to wake up the next day and be mad about it.  Little did I know it was just the beginning and within a couple of weeks things were about to change.
 
A couple weeks later Dan talked to me about the upcoming spring break.  He had his own car and was thinking about going down to visit Tijuana, San Diego, and then hitting the tourist spots in Hollywood and trying to see the Tonight Show live.  He had a proposition for me that he was hoping Sue and I would go along with.  Sue and I were planning on staying on campus as we didn't have a car.  He offered to pay for all the gas in his car and also he would pay for the hotel rooms wherever we stayed if for the entire week Sue would be willing to act as if she had two boyfriends the entire time, including having sex with him. 
 
The idea alone got my mind racing and I immediately told him I was definitely good with it and that I'd talk with Sue.  When I told Sue she was initially surprised that Dan would suggest such a thing but with a nervous smile she said, "I'm not going to say yes, but I'm not going to say no," and to give her a day to think about it. 
 
The next day she said she only had one question for me and that was if I was sure that I'd be ok with it and that if she at any time got too uncomfortable with it, that we could stop it and pay our fair share.  I enthusiastically said that wouldn't be a problem and that I was excited to see what it would be like.  When I told Dan her response he was obviously very excited as well but he felt it was important for us to get together in his room the night before spring break started just to make sure Sue was still ok with everything and to talk things out.
 
The night before we were to leave Sue and I went up to Dan's room and it was obvious everyone was a little nervous and there was some nervous chit chat until Dan finally broke the ice and said, "Look, I don't want us to get to Tijuana and Sue gets cold feet or that she feels pressure for the rest of the week to do anything."  With that he looked at Sue and said, "Can I kiss you?" 
 
Sue said, "I guess we might as well find out now before we've driven 12 hours to Mexico," and she went up to Dan and started making out with him.  Within seconds he was taking off her clothes and laying her on the bed.  As he was feeling her up, he then slid his hand onto her pussy and said, "If you want to fuck me during the week, spread your legs right now and raise your hips." 
 
Sue looked over to me for approval and with that she spread her legs and tilted up at the hips.  Dan stood up and pulled his shorts down.  He told her to grab his cock and to slowly slide it in her but that he wanted her to tell him something...and with that, as Sue slid him inside her moist cunt, she said, "This pussy is going to be just as much yours all week." 
 
Dan told her that he wanted to own it all week and Sue stared directly in his eyes and replied, "I want you to own it, I want both of you to own all of me." And with that, we left the next day for Mexico.
 


 

My girlfriend was raised in a very strict family.  We started dating our junior year in high school.  She was/is a beautiful blond with blue eyes and a fantastic body. 
 
Although she had previous boyfriends I was the first to feel her up.  By the time we went to college she was ready to be away from parental supervision.  This was back in the 1970s where it was fairly common to see tube tops and bralessness.  Her college roommate seldom wore a bra and when it was time for the first dorm party of the year I dared her to be braless.  Little did I know that this would be the start of an exciting number of years. 
 
She wore a thin yellow tube top.  Although it wasn't sheer, I (and everyone else) could tell she was braless.  Later on that night she told me it was kind of exciting catching guys looking at her boobs. 
 
Our school had a student exchange program and we both talked to our parents about going to the U of Miami for one semester.  Not surprisingly her parents said "no" as they wanted to see how her grades would be during her freshman year. 
 
Our sophomore year she finally got permission from her parents.  We went during the 2nd semester.  In Florida, braless is pretty much the normal look and she seldom wore one. 
 
There was a posting in our dorm looking for a female model for an event for Undercoverwear.  Undercoverwear was similar to Fredericks of Hollywood.  A woman sold Undercoverwear the way you would sell Tupperware, except it was lingerie.  I told Sue I thought it would be kind of fun doing something like that but only if I could go. 
 
Sue contacted the woman looking for a female model and met with her.  The "event" was going to be at a community hall that she had rented and the attendance would be exclusively for males.  The expectation was Sue would wear a variety of lingerie but there was no nudity required. She'd also get paid $100 for about 2 hours of work, and I could go. 
 
When we got there Sue was taken into a back room where there was a rack full of lingerie sorted out according to the level of sexiness and sheerness.  There were about 20 guys sitting at round tables of 5 that she'd have to walk around like she was on a catwalk so they could see what the outfits looked like. 
 
Sue had come out in a variety of sexy teddy's and negligees.  After the first couple outfits, the clothes became more revealing.  Toward the end she came out in an outfit that although not totally sheer you could see a hint of her nipples.  All the guys started clapping as she did her walk around all the tables. 
 
It was now the end of the "fashion show" and the guys started chanting for her to come out one more time.  The woman running it came up to me and told me that Sue wanted to see me in the back room before the show was officially over. 
 
I went into the back room and Sue could tell I had really enjoyed everything.  Sue then pulled off a "harem outfit" that was the furthest one on the clothes rack, indicating it was the most revealing.  She said she was fine putting it on as the last outfit if I was OK with her wearing it in front of all the guys.  I said, "Are you kidding me, I'd love it."  I then walked back to my table and the woman announced that Sue was coming out with one more outfit to end the night and asked for the guys to finalize their order sheets but that they may want to wait for the last outfit to add to their orders. 
 
Sue then walked out in a light pink harem outfit that was totally sheer exposing her breasts and nipples as if she was topless.  The guys went crazy.  They started yelling "tits for tips" and with that Sue looked at me and with a sly grin I nodded my head and she proceeded to take her top down and did a final walk around each table being completely topless.  When she got back to the room she was changing in, the woman walked in and handed her another fifty dollars in tips and said she had done a great job. 
 
As Sue and I were walking out to head back to the dorm a man who was at the fashion show was waiting for us and said that he owned a restaurant and if we both were looking to make a few extra dollars he could use us for about 4 hours every Saturday from noon to 4pm.  The restaurant was called "R Donuts".  The job for me would be to buss tables, and for Sue it would be as a topless waitress (hence the "R" Donut name). We told him we'd think about it. 
 
See part 2 as this story of the journey from shyness to hotwife continues.

My fantasy has always been to watch my wife get fucked by another man. We have been with another woman before which is a whole story in itself that I’ll tell you about later.
 
One night several years ago my wife and I had gone to a club. Not your ordinary club, but a good club for swingers and singles. The night had started out rather slow and we were not finding any action that I had hoped. My wife knows what she wants and that is what we go with. And that night we found what she wanted and it was such a great experience she knew she wanted to do it again. She had gotten fucked by a black guy and she had enjoyed it. So, when we got the chance, she wanted to try it again.
 
Being at a swinger’s club isn’t really her thing, but fucking in front of people or listening to them fuck is a big turn-on for her. Since we don’t live close to any swingers’ clubs or anything of that nature, we don’t get many opportunities to do anything like this.
 
A couple of years ago we got a chance to go to another club. Yes, one of those clubs. We were looking for a little fun and hoping to find something as good as the last time we were out. We talked to many people as the night went on and my wife was trying to figure out what we were going to be doing to have fun that night. There was a hot blonde that was interested in us and kept on grabbing my cock which my wife was loving because this was getting her going. My wife and I decided that this was not what we had in mind for tonight, so we just kind of let that slide and we went on to pursue something else. She said she would know it when she saw it.
 
My wife had put a couple of drinks down and was feeling pretty good now. She was a little more daring and said she wanted to go change outfits like she did when we had been to a club previously. We had brought the very same sexy outfit that was see through, so she went and changed into it. When she came back out, there was not one guy's eyes on anyone but her. Even the women were looking on in awe. She is a beautiful woman that knows how to control a room.
 
One guy came up to me and told me he was jealous. He said he would do anything to get to fuck my wife, but she just didn’t feel right with him, I guess. As we were standing around, in came this well-built younger black guy and I think she almost came right there. The look on her face was almost mind blowing. She got this horny grin and told me she was ready to start our night. As he walked by her, she gave him this dirty smile and took her hand and rubbed down by her cunt. He stopped walking and came over to her and asked if he could help her with anything. She just smiled and said that I think you already know what you can do. They danced around a little bit, but I could tell she couldn’t take it anymore, so she quickly unzipped his pants and took out his cock and grabbed it and lead him into another room like a dog on a leash.
 
I stayed back a couple of minutes to give them some time to get to know each other. When I did finally get to the other room, they had already undressed and she was sucking his cock. It was larger than mine. Not much longer, but thicker. I could tell she liked it.
 
My wife had picked a room where people would be able to watch if they wanted to. I stayed back in the wings and was kind of hidden so she really didn’t know I was even there.  As I watched my wife in action, I could tell she was enjoying every second of this guy’s cock. She was sucking it like there was no tomorrow.
 
Now it was his turn to return the favor. He got his face down to her pussy and started licking like it was candy. She was turning red and I could tell she was already about to cum. She was squirming and shaking and he was getting her cunt all ready for his big shaft. But before he fucked her, he now spread her legs out and started fingering her pussy to the point that she started squirting fluids all over the sheet they were laying on. It was like the flood gates had opened up and all the juices were flowing.
 
She finally had all she could take because I’m sure she had cum multiple times already and I could tell she just wanted to have him inside her. I heard her say to give me your big, black cock. He asked her if she wanted him to put on a condom and she told him no, she wanted to feel him inside her cunt.
 
He took her and spread her legs wide and slowly inserted his bbc into her tight cunt. She told him to go slowly because she said it was so big that she needed to get used to it. After several minutes of the slow movement, she said she needed him to fuck her harder so he started to go full penetration into her dripping wet cunt. She was telling him how good his cock felt, and how she loved fucking him.
 
They switched positions multiple times with her sitting on top of his cock and riding him like she has never ridden before. My wife took his whole cock inside of her as deeply as she could, rubbing back and forth and cumming time and time again.
 
They finally switched back to missionary style and were fucking hard when I heard her say to him, she wanted him to cum in her pussy. She said she wanted to feel his cum drip out of her pussy all night long. When he heard her say that, he started to pick up the pace and finally started moaning and said he was about to cum. My wife was now cumming herself and as he shot his load inside of her, she started squirming and shaking with every pulse of his exploding cock. Her body was red from all of her orgasms, and I could tell she was getting worn out. They had gone for almost 40 minutes of nonstop action. Not to mention that all the other people that had gathered around to watch started going to other parts of the place as they had gotten a show that they would remember forever.
 
When he pulled his now soft cock out of my wife, I could see the cum dripping down her ass. She was getting what she wanted, I guess. She would be able to feel his cum dripping out of her the rest of the night. But I didn’t realize that she was not done yet. She wanted more. My wife took his cock and started sucking on it again. I guess he was young enough that almost instantly he got hard and she took his cock and guided it into her cunt and said she needed more of his cum. He fucked her for another 10 minutes until he exploded with more cum inside my wife’s pussy again. Again, as I watched the cum drip down her ass, she was getting what she wanted. She was going to feel this the rest of the night.
 
They both started cleaning up a little and I slowly came out of the crowd that had gathered. She saw me and gave me that dirty little smile she sometimes gets. My wife asked me if I had enjoyed her show. She said she needed to have a little more cum in her pussy tonight and she now wanted mine. Her new little friend just kind of sat back in the corner and decided to watch us.
 
I knew I wouldn’t last long because I had almost cum multiple times just watching her. With some of the crowd still watching I got undressed, and slid my wet with pre-cum cock into my wife’s cum-loaded pussy. I fucked her until she started cumming. Her cunt convulsed so hard that it squeezed my cock and made me start to cum. I came in her pussy, mixing my cum with my wife’s new fuck buddies cum. I pulled my cock out and watched it all slowly slide down her ass. She got up and went over to our young fuck buddy and she gave him a long passionate kiss and said thank you for such a great time. He gave her one last little finger fucking and handed her a card of his if we were ever in the area again.
 
He left after he got dressed and we got cleaned up and went out to the main room. I had multiple people including women and even the bartender say that my wife was one of the women they would like to fuck if they ever got a chance after seeing her in action. I guess I’m the lucky one here.
 
Later that night when we were driving to our resort, she slipped her hand down pants and put her fingers in her pussy. She brought them out and rubbed them on my face. She smiled and said we gotta do this again sometime as we pulled into the parking lot to call it a night.
 
And what a night it was.