3 comments/ 27789 views/ 25 favorites Double Teamed By: HockeyCH9 This is my first crack at story writing. Some of the details have been slightly exaggerated and the names have been changed to protect the identities of the not so innocent parties involved. Everybody mentioned in the story is above eighteen years of age. And being a hockey player my vocabulary is pretty vulgar. Be honest and leave some feedback to help me improve my writing skills and give you all a better experience. Thanks! ***** Only three more weeks until my best friend Tyler goes back up to school for the year and I have to wait another three months until we get to get drunk, watch sports, talk about chicks, and play video games for seven hours straight. It became something of a regular occurrence for us that summer going into our sophomore years of college. We've been inseparable since the eighth grade when both made the same hockey team. As we grew up we went from immature kids who talked about all the girls we wanted to kiss, to young men who figured out how to sleep with the hottest girls that our friends could only dream about. We were quite the one two punch when it came to slaying pussy until I started dating my current girlfriend of a year Robin. I knew everything about Tyler; his taste in women (he's an ass man), the moves he uses to pick up those behindly gifted women (he liked to use the sympathy act), and, after showering with him six days a week for almost ten years after hockey, his dick size (roughly six inches or so with medium girth much like my own). After a week of helping me move into my new apartment Tyler and I decided to finally relax and have one of those infamous drunken video game marathons. "SUCK MY DICK JESSE YOU COCKSUCKER!" Ty screamed in my face as I threw my controller across the room after he scored an overtime goal on me in NHL 15. After he calmed down he began to tell me about this girl from high school that he finally ended up fucking after years of trying. "Very selfish, it would've pissed me off if her pussy didn't taste so good." He began as I almost spit my water all over the room in laughter. Although this was exactly the type of comment I expected from him it was still just as hilarious. "I licked her pussy and ass for almost twenty minutes before she let my dick near it. I did all of the fucking work J. I was top for a minute then flipped her and fucked her from behind for another five minutes until I finally jizzed in her mouth." "At least you got to shoot it in her mouth," I replied. "Pfft, she spit the shit out Jess. Huge let down for eighteen year old me. I used to jerk off to the sight of her ass in her gym shorts as soon as I got home from school. So how are things with Robin?" as he tried to change the subject away from his disappointed fantasy. "Good dude, really good we just planned a vacat-" I was interrupted by a once again disappointed Tyler. "DUDE, I meant how's the sex? I don't give a shit about your corny ass couples vacation" I should've known, especially since we tell each other all of the details of our sexcapades." "You're such a douche," I joked. "But she's been on another level lately Ty. I don't know what it is but Robin has wanted to try all this new shit. She told me to finger her ass while I was fucking her from behind the other day. She bought some restraints and I tied her up and ate her pussy until she couldn't handle it anymore," I explained to a very intently listening Tyler. "I don't know what it is and I don't really give a shit either." We both let out a howl of laughter as the door cracked open and a short blonde girl who I immediately recognized as my girlfriend and roommate Robin walked in and let out a small chuckle at us and walked into our room to change out of her work clothes. She came out in tiny pair hot pink of shorts that showed the bottom of her tight little ass cheeks and a tight blue tank top which didn't have a bra under and her perky C cups were protruding out. I saw that her clothing or lack thereof, caught Tyler's attention as she walked right in front of him to sit on my lap. Seeing her tight body and my best friend's reaction to that body got me halfway hard and I wasn't exactly hiding it from Robin. "Well hello to you too," she said with a smirk as she sat down giving me a quick kiss and rubbed her ass on my semi hard cock. We were very open about our sex life especially to Tyler and Robin's best friend Sarah. Tyler decided he was going to spend the night and after a few more beers by all three of us and two hours of conversation most of which consisted mostly of sexual preferences, Robin goes into the other room to call her mom before she goes to bed. I leaned over to Tyler after watching him stare at my girlfriend's ass and readjusting the bulge in his pants and asked him if he'd mind if we fucked after we went to bed. In his charming Tyler way he answered with, "Nah man, take that pussy to pound town for me. Besides I'll be able to hear and rub one out myself so make it loud enough so I can hear," which made me almost fall off the couch in laughter. After I came down from my hyena-like cackling, I had an idea that I never thought I'd get away with: I want my girlfriend, the love of my life, to suck and fuck both of us at the same time. I mentioned it to Ty and with that same bulge in his pants he was all for it. The hard part was getting Robin on board. My only shot was that she has been extremely horny and open to new stuff lately and maybe she'd go for it. After twenty more minutes of anticipation Robin came out of the room relieved to be done with that conversation and she came to sit on my lap on the other end of the couch opposite of Tyler. It was getting late so I grabbed a few more beers for everyone and put on the Wolf of Wallstreet on Netflix. Two minutes into the movie I shoot a look over to Tyler and we both nodded. I pulled my arm out from behind her and slowly moved it toward her pussy. As I started rubbing her clit she let out a soft moan and leaned in and whispered a word of resistance because Tyler was three feet away but didn't pull my hand from her moistening pussy. I whispered back, "Let's just do it. He won't care." "That would be torture to have to watch that," she rebutted. I finally decided to just go for it, "Then let's have him join in." She wasn't sure it was a good idea but after some more massaging of her pussy and to my surprise she finally just gave in. Besides she wasn't hiding much with all of her moaning and squirming, all Tyler could do was laugh because he knew what I was up to. After ten more minutes of getting her ready to go she slithered off the couch onto her knees on the floor. She unzipped my pants pulled them all the way past my feet which showed me she was all in, and whipped my five and a half inch with a slight right hook fully erect cock out. She slowly flicked her tongue across my head then lowered her mouth onto my shaft. Bobbing her head up and down on my cock I can feel it slipping down her throat. At this point I'm not even trying to hide my pleasure letting out sighs every few seconds to the point that I almost forgot Tyler has been watching this whole thing unfold. I nod my head and motion for him to scoot closer so Robin could reach him and get my whole fantasy started. She reached over and pulled his dick out with one hand without even breaking stride on my cock. No surprise to either of us he was already hard. He was a half an inch bigger in length but slightly smaller in girth. Tyler helped her in the spirit of what was to come and pulled his pants past his ankles. She stroked his cock faster and faster without losing even a step on me. She finally moved over to Tyler. It was so erotic to watch my girlfriend suck my best friends cock. I almost came just watching that so I had to recoup so I didn't blow my load before we even got going. For the next ten minutes she alternated between sucking my cock and jerking off Tyler and vice versa. This was by far the most erotic and pleasurable experience I've ever been a part of. By this time all three of us were completely naked. I wanted to switch things up a bit, so I stood up while Robin had her mouth around his big hard cock and pulled her ass up bent over so she was now standing but her mouth never left Tyler's pole. I stuck my finger inside her pussy to loosen it up a bit. From previous experience with her I know that her tight pussy in combination with my above average girth isn't always best combination when it comes to initial penetration. I could feel her loosening up just enough for my cock to fit as I continued to finger her. I couldn't wait any longer. Watching my girlfriend's mouth go up and down on my best friend's cock was so erotic. It turned me on to a level I've never been before; my cock was just throbbing while I was jamming my fingers in Robin's tight dripping wet pussy. I pulled my two fingers out and the air became filled with the smell of pussy. I wedged my rock hard dick inside of her dripping hole and she let out a moan meanwhile not stopping sucking Tyler's shaft. I could tell that we were all having the time of our lives. Tyler had his head tilted back breathing heavily on the couch, Robin was standing bent over so she could blow a strange cock while having a familiar cock pounding her from behind, while I was horny as hell watching my girlfriend get face fucked. In and out I thrusted as my prick barely fit in Robin's pussy. She loved when I was forceful and made sure she knew that that was my pussy. My right arm was wrapped around rubbing her clit just inches above where was she was being pounded ruthlessly and my left hand was palm down on her back as I thrusted softer giving her a chance to catch her breath before I caught her by surprise and sped back up and pounded her from behind until she let out a screaming orgasm onto to cock that was shoved deeper in her mouth. She continued to breathe heavy and her yells got softer and softer until she reset and prepared herself for the next orgasm. After two more intense orgasms in a span of five minutes I decided that what was happening wasn't enough. Against my original plans I pulled my now sore but still fully erect cock out of Robin's steaming pussy and walked over to the loveseat where Tyler was sitting and tapped him on the shoulder because his eyes were closed and mouthed, "Go fuck her" and pointed to the back end of her body that was now kneeling. Of course he didn't need to be told twice as he jumped up and ran up behind her and stuck his saliva-lubricated subtly longer cock in her slit. She opened her eyes and looked up to put a dick back in her mouth and was slightly shocked to see me there while realizing that it was Tyler's penis inside her. After a look of approval and a nod of acceptance from me she sucked my cock and sucked all of her own juices off of her man's dick. Her lips were tight around my shaft bobbing up and down faster and faster while she got slammed back on a strange dick. I'm not sure if it was the new experience or if he was just that good, but he made her cum within a minute and a half. She let out constant peaks and valleys of ecstasy and relaxation trying to recover for what seemed like every ninety seconds for the next ten minutes. Robin's moans turned me on so much that I knew I wouldn't last much longer. I ponytailed her short blonde hair with my hand and pushed her mouth onto my cock to the point where she was almost choking, which she loved going back to how she wanted me to make sure she knows she's mine. "You want me to cum down your throat?" I exclaimed while still holding her hair almost as if I wanted to make it known to the world. Between breaths she let out a soft yes before another harsh orgasm came bubbling to the surface. With a fistful of hair in hand I controlled her head as I neared closer to my breaking point. She knew what was coming and opened her throat to allow my cock to slide down. My cock jerked and my warm cum shot out like a canon firing. I moved my dick shallower in her mouth so that she could get the taste of my cream in her mouth and she sucked the last few drops of cum from my dick like a straw but she didn't swallow and she spit my cum back on my own cock which was a favorite move of hers. She waited a few seconds and let my jazz slide down my shaft then flicked her tongue and slurped it all back up and swallowed it, which of course I loved, the sloppier the better in my opinion. After she finally let me get up and I walked away while she was still getting fucked by Tyler he kept thrusting his hips into her for another two or three minutes until he voiced that he was also getting close to finishing. Tyler looked over to me and asked where I wanted him to cum because he didn't want to cross any boundaries. Instead of addressing the question directly I decided to give her one last command; "Grab those titties and let him cum on them." She nodded in understanding and right on cue he pulled his dick out that was layered with pussy juice and stroked his dick until his cum shot out onto her perfect C-cup boobs and pooled up in between them because she was squeezing them together. She let out a few more moans as he squeezed the last few drops of cream from his shaft. I tossed them some toilet paper because I was the only one dry enough to go get some without tracking a trail of cum through our brand new apartment. They wiped off and we all just collapsed all over the couches and floors in exhaustion. We just sat there with Wolf of Wallstreet still playing in the background and just let out sighs of satisfaction until we finally fell asleep sprawled across the living room butt ass naked. I rolled over the next morning to see a pair of tits, a bare and abused pussy, and a dick hanging out attached to two naked bodies. Just as I shook off the fog of sleeping the two previously sleeping nude people began to stir and awake from their respective slumbers. I was expecting a bit of awkwardness but everything was as normal as it could be. We got up threw some clothes on and conversed a little, mostly about how crazy we were about last night. There was no mention of if this would happen again but I'm sure it was on everyone's mind. After a few minutes of conversation followed by two hours of video games Tyler had to leave to go back up to school. We said our goodbyes and he went on his way. Just as he was about to walk out the door he gave Robin a quick slap on the ass and just before he turned the corner in the hallway he turned back and shot me a wink and a quick salute that only Ty could. And just like that the most erotic experience of all of our lives was officially over. But this would not be the only time... Double-Teamed Mom I'm going to give the background quickly -- not because I can't expound on it or don't remember details, but because I want to get to the action because everytime I think about it I smile and get hard.. I'm Jason, 20, and have an identical twin, Justin. We go to different colleges. We are so identical only our mother can tell us apart in daylight; no one can at night, or by our voices. My father was a domineering asshole who ran roughshod over my no-self-esteem-mother, and left when I was 15. The only good thing about him was that he made a lot of money and set up college trust funds for Justin and me, and my mom got enough in the divorce to live fairly comfortably. However, his leaving turned her into a drunk and made her chronically depressed. She always wore just sweatsuits, inside or outside the house, no makeup, wild hair, and didn't tend to her appearance in any way. Mom, now 42, was brought up strictly and I found out recently Dad was the only person she had sex with, and only a few dozen times in 16 years of marriage, and all slam, bam, thank you ma'am experiences; and no one had ever eaten her pussy. She thought it was because she was deficient. Therefore she wasn't looking for someone else after he left. Justin and I have always been completely well adjusted despite our parents, maybe because we had each other. We did well in school and sports, and got our fair share of tail. By the start of the summer of 2010, we both had gotten several dozen blowjobs, and fucked (with condoms) at least eight or ten girls each. Our only bareback experience was when we were 18 with a 33 year old neighbor, Jiant Jugs Jenny. She had a homely face and just above average body, except that she had the biggest natural tits for a slim-waist woman you could imagine. She had a twins fetish so we double teamed her, one doing her doggy when massaging those geological wonders on her chest while the other got a blowjob, and then switching. Then we would each suck a tit for about half an hour while lying next to her as she chatted away. We were real sorry when Her Jiantness moved after about ten encounters. Her tits became my screen saver. Anyway, Justin and I went to a shrink on our Mom's behalf the summer of '09 and blackmailed her into getting help. At the shrink's urging we told her we would never come to see her again after we went to college unless she enrolled in a drunk program and saw the shrink about her depression. It worked. By the time we left for college in September '09 she was making progress on both fronts. I heard about a special spa not far from her house from a friend at college, and Justin and I bought her the first two months membership for Christmas. She seemed to be making such good progress that both Justin and I got summer jobs in our home town and told her we wanted to live at home during the summer. We hadn't seen her since Christmas. I got home early June, a few days before Justin. I had only a suitcase and my laptop, having left everything else at my off campus apartment, and got dropped off by a friend at the end of our block. As I walked to the house, I saw a real Babe outside the house working in the garden. At first I thought it must be the wrong house -- but it wasn't. She had long slender legs with a light uniform tan, that ended in a Kim Kardashian ass, covered only by some skimpy jean shorts. Her tanned midriff was bare. She had long nicely combed radiant light brown hair, and a skimpy tank top that seemed to be --as best I could tell -- barely covering a real nice set of bonkers. When I got closer I still didn't have a good view of her face, but what I could see looked real nice, highlighted by light makeup. Being a horny red-blooded male who hadn't had a good screw in a month and no prospects for the summer, my mind was in full blown fantasy about fucking the Babe's brains out as the crotch of my pants was starting to tent. When I approached the Babe from behind I didn't want to startle her so when about 20 feet away I said "Hi, I'm Jason, Joyce's son. Are you a friend of hers?" When she spun around I almost shit my pants -- it was MOM. She apparently thought I was just being nice with my comment, smiled, ran up and hugged me tight. I hugged back with my head on her shoulder, trying to gain my composure and suppress my rising tool at the same time. When I finally thought I had sufficiently succeeded in both, I released my hug, told her she looked fantastic, and we went inside arm-in-arm. I'm not sure how coherent I was while we sat at the transparent kitchen table, drank lemonade, and chatted for the next three hours. The glass table was a joy and a curse -- it made it easy to ogle her body, but shit, it was my mother! My mind was addled; but I remember the most important information. For brevity, I'll summarize the relevant parts of our discussion. Mom's shrink pronounced her cured of depression. She hadn't had even one sip of alcohol since August 15, '09. The people at the spa were miracle workers (she got that right) and she had gone there at least three hours a day six out of every seven days since Christmas. She realized that her appearance had changed dramatically (understatement of the decade). The exercise and clean living regime she was following made her feel fantastic but horny (not her word, but I was so shocked she would even talk with me about stuff like that I can't remember her exact words), but she still had no confidence to date. That night we went out for dinner at a restaurant she used to like but hadn't been to since the asshole left. She wore a mid-thigh length sleeveless yellow sundress, a pushup bra, three inch yellow heels, and gold choker. Except for stress lines in her face, she could have passed for 30. I said "Mom, you're one of the hottest women I have ever seen!" She blushed slightly, and dismissed my comment as a son's prejudice, but she was obviously pleased. At the restaurant I pointed out to her all the guys who were ogling her. Each time she had the same reaction as to my "hottest" comment, but clearly got more and more pleased and confident. On numerous occasions I put my hand on her bare knee, stroked or squeezed it. I stared into her big blue eyes every chance I got. The restaurant had a dance floor with a great DJ, and after a wonderful meal, I asked her to dance. Time for another shock! She danced like a pro -- lessons at the spa she said -- and the movements of her body, whether intentional or not, were as seductive as a courtesan's! My circuits were close to overload. We didn't leave the restaurant until midnight, three hours after her bad-old-days bedtime. She was still lively so we went sightseeing in our own city, something we hadn't done since I was a child, and took a long walk along the river park. I put my sport coat over shoulders, and we held hands and chatted like we were on a date. We got home after 2 a.m. By then was she a little bleary-eyed. Having just come from keeping late hours at school, I had a distinct advantage over her, and for better or worse used it. She gushed about how tonight was the most fun she had since she could remember, but then tears welled up. It was then she laid on me her lack of sexual experience, including the bad-to-nonexistent marriage sex, I reported earlier and said tonight made her feel like she really deserved a real sex life but she had too much fear to progress in reality, and she started to sob uncontrollably. I would like to tell you that what I said to her next was motivated by pure interest in her well being, but you would know it was a lie; it was about me, with the hope that it would also be about her. I asked her if she thought she could start a sexual relationship with someone she knew loved her and would never hurt her until she gained the sexual confidence she needed. She interrupted her wild sobbing, and looking directly at me through her running mascara and weary eyes said that would be great but she didn't know anyone like that. At that point I stood, lifted her off her chair, planted a lecherous kiss on her lips, and started carrying her to my room. I know that given her fatigue and lack of confidence, and the abruptness of my movements, at first she was puzzled. However, as I laid her on my bed she started to realize that I was not acting like her son, but like her lover. She protested, but was too tired, emotionally spent, and overwhelmed to put up a fight as I pulled off her panties and started tonguing and licking her cunt. She cried the first few minutes I was ravishing her clit and pussy lips, but as soon as I penetrated her with two fingers and found and started abusing her G spot, all sounds stopped except for pleasure moans and screams. She orgasmed at least twice in the first minutes -- maybe the first real orgasms of her life -- and by the second climax I knew she was mine to please or punish as I saw fit. I gently undressed her while constantly paying attention to her pulsing underused pussy, sucked her glorious tits while undressing myself, and then told her she was going to get a real fuck from someone who really cared about pleasing her. I turned her on her hands and knees, and jammed my tormented rock hard dip stick between her succulent lips, causing her to shriek. I pumped slowly at first, listening to her reaction. No more sobbing, just sounds of pleasure and "Oh My God". I started pounding like a jackhammer. Once she climaxed again and I unloaded every ounce of joy juice I could into her, I laid her down on her side with my throbbing dick still filling her snatch, and wrapped my arms tightly around her while nuzzling her neck. Not only was I as serene as I ever was in my life, I could sense her contentment too. We both fell into a blissful sleep within minutes. When I awoke the next morning, except for the involuntary withdrawal of my now flaccid penis from her pussy, we were in exactly the same position we fell asleep in. I gently kissed her neck, shoulders, and cheek and she started to come out of her sex-induced coma. I continued my gentle assault on her body parts until she finally gained enough awareness to realize where she was and remember what had happened. She turned over in the bed briskly and stared into my eyes. Before she could say anything I pondered "How does the hottest woman in the world feel today?" She blushed, opened her eyes even wider, but then in a somewhat choked voice said "Jason, what did you do to me?" I responded "I loved you like you deserved to be loved your whole life and should be in the future. Did you enjoy it?" Her eyes started to softly well up with tears again as she stammered "It evoked the best, most intense, feelings I ever have had in my life, but it is so wrong...." Without letting her finish, I put a finger on her lips and said "What is wrong is the way you've been treated the rest of your life. If I could have made you as happy as you were last night some other way, I would have done it, but that wasn't going to happen. Now, I'm going to teach you everything I know about how to fulfill a lover and only when I've done that will I stop -- unless you are so fucking amazing that I have to make love to you the rest of my life." With that, I started kissing her open mouthed while tweaking her nipples with my left hand, and rubbing her stupendous ass with my right. She made a token effort at resisting for about two or three minutes, but realized it was futile, and ultimately submitted and groaned like a rusty water wheel as I fucked her senseless in the missionary position. For the next few days we fucked like minks whenever I wasn't at my summer job and she was home from her part time work. I had never seen her so upbeat at any time in my life, although she mock complained several times that I was keeping her from the spa when I demanded an afternoon carnal session. The day before Justin was to arrive, at breakfast she said "What are we going to do when your brother gets here?" I said I wasn't sure but after a few days I might have to tell him flat out what was going on and I knew what his reaction would be but didn't want to tell her yet. She got a quizzical look on her face when I said "When he comes home tomorrow, wear the same outfit you did the day I showed up." She wasn't happy with my response, but didn't push it, and nodded. Justin and I told each other everything. I had already informed him about Mom's transformation and told him I was fucking her twice a day. At first he didn't believe me, but I convinced him when I told him if he didn't like it he could move elsewhere during the summer, but if he was amazed as I was about the change in Mom he could get his own piece of the action since she was exhausting me. I told him there was no similarity between the woman I was porking now and the mother he remembered. Justin's arrival worked out as I had hoped. When he saw Mom's ass in her jean shorts -- he was even more of an ass man than I was -- her perfect pelvis, her perky tits, and how happy and content she looked and the ease with which she conversed with us, he took me aside and demanded his "cut". That night, he pretended to go to bed in his room before Mom and I, which made her feel better since she thought that then he might not figure out that she and I were sleeping in her bed. Shortly after we went to bed and I started foreplay, I excused myself to get a drink of water, and she requested some too. Per our prearrangement, Justin was waiting for me in the kitchen, he took two glasses of water into Mom's dark bedroom, and he started in where I left off. I voyeuristically listened at the door as I heard her muffled screams as he pounded the shit out of her twice. When the banging subsided I went to my room, only to be awakened about 7 the next morning with more banging. I got up and was reading the paper when Justin came into the kitchen with a mile wide smile. His words "wholly shit, bro, that was the best sexual experience of my life. I never got it up three times in eight hours before, and certainly not with that much cum." My loving brotherly response "I don't want to hear about your sexual inadequacies. Did Mom figure out it was you?" He retorted, "Not last night, when she kept calling me Jason. But in the morning light she recognized me instantly and looked distressed when she asked if that were me last night. I told her 'you figure it out for yourself Mom' as I dove for her pussy, licked up a storm for ten minutes, and then made her ride me while I pounded her harder than I ever pounded any other woman in my life, including Jiant Jugs Jenny." Mom came out to breakfast about ten minutes later. I had prepared her favorite - strawberry waffles with whipping cream, two strips of bacon, and a pot of tea. Her initial sheepish look turned to one of joy upon seeing the spread, and as I helped her to her seat she smiled. After a few minutes of small talk about the breakfast and the weather, she asked if she had any say in our plans for her. I responded, "Mom, as you already know, you are the hottest woman in the world. Too much for either one of us, but we would love to alternate days as your lover to keep you happy and our plumbing in good working order. PLEEEEEEASE". Seeing the looks of expectation on our faces, she laughed, and said "Wow, in less than two weeks I've gone from being incapable of getting laid to being too much for one 20 year old to handle by himself. As long as you give me one day off a week to go to the spa, I'm in." What followed was the best summer of our lives. Mom got Thursday off, but every other day Justin and I fucked her at least twice each day, and ate her whenever the opportunity presented itself. Just when we thought things couldn't get any better, about ten days before we both had to go back to school, while sitting at breakfast naked, Mom posited "I've heard that anal can be fun; you boys know anything about that? I've also heard that some women dream about a Double Penetration. What do you boys think?" Since all our blood had immediately rushed to our dicks we had none in our brains to allow us to think. Plus we were shocked, but had to play it cool since we were the ones teaching Mom about sex in view of her horrible love life prior to June, 2010. However, since both Justin and I were 100% certain that she was the best fuck in the world we needed to snap out of it. God, we loved everything about her, her passion, her soft vibrant pussy lips, her supersensitive glistening half inch clit, her easily stimulated G-spot, her hemispherical ass, her tight vagina, her succulent tits, her high libido, her infinite kindness -- shit she was the whole enchilada! Now that we had brought her to a sexual epiphany, we had to follow through even though we were getting past our comfort zone. While we each had a few condom anal experiences, we were by no means experts, or even entirely comfortable. Especially since we knew some women hated anal, and one of our main goals was to treat Mom with the utmost respect, we had to proceed carefully. I started out by directly answering her questions "I've heard that anal can be fun; you boys know anything about that? I've also heard that some women dream about a Double Penetration. What do you boys think?" My thoughtful response "Mom, anal can be fun, but you have to proceed carefully because it can be painful, and some people don't like it. As far as a DP is concerned, if someone really likes anal and has two partners they are comfortable with, a DP can be very satisfying. Justin and I are more than willing to help our phenomenal sex goddess Mom test these out -- we just need to be careful." With that, she smiled broadly, got up, put her arms around my neck and kissed me, and said "Well you're up tonight Jason. Let's give anal a try." I smiled back, grabbed her bare ass and said "You're on". While Mom went to get dressed for work Justin said "Dude, I hope you know what you're doing. The idea of doing a DP with Mom has hijacked my brain, but we've got to be really careful." I responded "I know, bro, we will be; but the satisfaction we would get by doing it successfully is worth the risk. It will make our experience with Jiant Jugs Jenny ho hum." Despite my bravado, I was really apprehensive, so at lunch time at work I got on the Internet and read as much about anal as I could. I bought the perfect lubricant at a drugstore on my way home, did more research after work, and was ready. I was especially attentive to Mom that night, helping her prepare dinner, and gently kissing her neck, and stroking her ass, every chance I got. After dinner the three of us played a board game, and about a half hour earlier than normal I put my arms around her neck, kissed her, and whispered in her ear "I want you real bad tonight you sexy goddess. Can we get between the sheets now?" Without a word, she stood up, kissed Justin good night, and had her top off before she got to her bedroom. I impressed upon Mom the need to be sure to tell me everything about how she was feeling while I was handling her anus because we had no idea what to expect. She smiled and said "I will, but I'm not a fragile doll. Do what you need to, we can post mortem it afterward." I rolled her on her stomach, kissed and squeezed her firm bulbous ass cheeks for a few minutes, then ran my tongue over her rosebud. She flinched at least a half dozen times as I flicked her asshole. Then I spread lubricant on her brown hole with my fingers, and slowly inserted a first lubed finger until it was completely buried. Mom gasped, then purred. Over the next fifteen minutes I lubed and gently inserted a second and then third finger, and moved them around. She gasped with each new finger insertion, and then purred as I moved my fingers in reciprocating and circular paths within her tight hole. By this time my cock was rock hard, and in need of attention. I told Mom it was time to go all the way, and she raised her ass in the air, I straddled her, and slowly inserted my lubed cock head. After minor resistance and a small moan from Mom, my dick slid right in and we both exhaled with relief and pleasure. Double-Teamed Mom I pumped gently, never even approaching the rough pussy pounding that Mom had come to love. While Mom had an unusually tight pussy, as is normal her asshole was even tighter, and it wasn't long before I was ready to blow. When I did I felt Mom had a minor climax herself. After depositing my complete load, I stayed stationary in Mom while gently massaging her tits and kissing the back of her neck, until I became flaccid enough to easily withdraw. Once I did withdraw, Mom grabbed me by the neck and said "Thank you Jason. I feel your love so intensely and I trust you completely. I loved your gentle approach and want to do it again some time." We got up, showered, and after cleaning each other off completely, I lifted her up by her thighs, pushed her back against the shower stall wall, and fucked her pussy hard. We had a virtually simultaneous climax that was dangerous because it almost collapsed my legs. After drying each other off, we returned to bed and fell asleep in each other's loving arms. The next night was Justin's. I told him everything I had done and suggested a repeat of the anal part, which he was happy to do since he had been even more apprehensive then I had. After the two introductory nights of anal, I decided to give Mom a preview of a DP and went to a sex store and bought a string of small diameter ass beads. That night I told Mom we would have a kind of dress rehearsal of a DP, and with her ass in the air I stimulated both of her rear orifices with my tongue, fingers, and lips. I then gently inserted the lubricated ass beads to a combination of pleasure and pain moans and groans, and then inserted my stiffy in her waiting slick cunt and started pounding her doggy style really hard, which she loved. As she started her climax I gently but continuously withdrew the ass beads. She squirmed, bucked, screamed, and shuddered for a good sixty seconds - until at least ten seconds after the last ass bead had popped out. Her reaction turned me on like a lighthouse, and after I discarded the ass beads I grabbed her firm boobs and pounded her like my life depended on it. When I blew in her, she screamed again, and then collapsed. I lay with my dick still in her for about two or three minutes, but there was no movement from her, only a few muffled sounds. Concerned, I withdrew and rolled her over to attend to her. Her eyes opened in a few seconds, and then she took a few deep breaths and said "Wow. I passed out. What a feeling. Every nerve in my body has been overloaded. Thank you a thousand times." With that she pressed her lips hard against mine for a few seconds, and then literally collapsed again. It was clear that we would have no second fuck tonight, as we normally did, but I was almost as drained as she was, and could care less. As I drew her into my arms I let out a sigh of ultimate contentment, and fell asleep. The next day was Thursday, her day off from Justin and I harassing her. We talked with her before she left for the spa, and we all agreed we would do a DP on Saturday when we were all off work, and that Justin would do anal with her again Friday. We agreed that Justin would enter her pussy and I her anus when we performed our DP. With great excitement and anticipation by the three of us, Saturday arrived. Justin and I took Mom to a great breakfast buffet. Then we went and sat by the community pool for a few hours, had a nice swim, and then agreed it was time for FUN. Mom looked radiant as she exited the shower. She had shaved her legs and armpits, used her favorite shower gels and shampoo, and smelled and felt fabulous. She insisted on wearing a fake pearl necklace Justin and I gave her when we were teenagers. Per our agreement, we laid her on new silk sheets that we had put on her bed, and I stimulated her pussy while Justin licked then lubed her anus. As I continued to work her pussy she insisted on taking Jason into her mouth. Once she sucked him steel hard, he lay down on the bed and she pussy mounted him. After pumping him a few minutes she bent over and stuck her butt in the air as high as she could. I was rock hard myself when I straddled her ass, and slowly inserted my lubed dick into her anus. Justin lay still as she shook her ass to help the insertion, and once I was fully inside her I said "Mom, don't move, and if either of us is pumping too hard, tell us to slow down". I took her "Oh my God!" as understanding. Justin started bucking upwardly while I was pumping forwardly. We started out slowly, but after a few minutes increased our pace. Mom continuously let out a low guttural sound. After a few minutes we were all sweating profusely but in emotional heaven. About ten strokes more and I was ready to cum. Justin told me to slow down, and in another dozen strokes he was ready and let me know. We came in Mom almost simultaneously and she let out a banshee scream the likes of which we had never heard before, and completely collapsed on top of Justin. He stayed in her while I gently withdrew and wrapped my arms around her. When Justin went flaccid we rolled Mom over. She was smiling, but virtually comatose. We tenderly gave her a sponge bath with warm water, turned on by her coos and sighs. Then we gently covered her, and let her sleep. It was the best family bonding experience in our history. Justin and I went out to shoot some hoops, and when we returned there was Mom in an outfit highlighting all of her sexy features preparing what she knew was our favorite dinner. We thought she was happy and fulfilled before, but that was just the tip of the iceberg. She was the most bubbly, effervescent, truly satisfied person we knew. After dinner, as she was serving us home-made key lime pie she put a hand on each of our crotches and said "I'll be visiting you boys at school this year. I hope you'll be ready for me." Knowing that there was no girl either of us had met at school that could hold a candle to our sexy Kim-Kardashian-ass mother, I don't know what grew faster. Our smiles or boners! My screen saver is now my mom's pussy.