The sensations I was feeling as Jake’s cock slid deeper into my ass were everything I hoped they would be. I could feel my sphincter stretch as the head of his dick passed through it. I looked at my naked wife sitting in the bedroom chair, her legs splayed open, her hand pumping her fingers into her pussy. As Jake’s hips bumped into my ass cheeks I moaned from the fullness I felt with all his 8 inches of cock buried inside me. I smiled as I wondered back to the night this all started.
It had only been a week since that night I had tried to fuck Mandy in her ass and her response to it. Mandy and I had married a little over a year ago. We were great together in everything we did. Including sex, but we had never engaged in ass play. Then one night when she was out with her girl friends I was surfing the internet and decided to check out some porn for kicks. When I opened the page the first video thumbnail showed a woman on her knees taking a big dick up her ass. I felt my dick stir as I looked at the image on my computer screen. I knew about anal sex but had never considered it appealing. There was something about the image in that that thumbnail that drew me in. I clicked on it. When the video started the couple were in the typical missionary position and he was giving her all he had. The camera angle was a close up from behind so her legs were spread wide and his dick was shiny with her juices as he pounded into her wet pussy.
Suddenly the guy withdrew and sat back on his heels and told the woman to turn over. She turned over and got on her knees. The man guided his cock to her pussy and ran the head through her pussy lips until he was completely between her legs. When he pulled back his cock slid through her lips then up her crack until the head stroked across her asshole. The woman moaned loudly and pushed back against his cock. He slid it back down and entered her wet pussy. The camera angle had changed to an overhead shot as he pistoned in and out of her. As he slowly fucked her he wet his finger and slipped it into her asshole to the first knuckle. The woman moaned as he fucked her in both holes at the same time.
Then I heard her ask him to fuck her in the ass. I was intrigued, wondering how she was gonna be able to take him there. His cock looked too big to fit in her tiny asshole. The guy stroked her pussy a couple more times then pulled out and positioned the head against her asshole. He slowly pushed forward and her anus expanded to except the head of his dick. When the head was completely in her he stopped. After a few seconds the woman begged him to put it all in her and fuck her. My dick was hard and there was a wet spot on my shorts from the pre-cum leaking out of it. I watched entranced as the guy slowly pushed the entire length of his cock into the woman’s ass.
Without realizing it I had pulled my dick out and was stroking it as I watched my first ass fucking. I was ready to cum before the guy in the video so I stopped masturbating. I couldn’t believe how turned on I was. When the guy was ready to cum he pulled out and shot his load all over the woman’s ass cheeks. That was it for me. I turned off the video and went to the bathroom to finish getting myself off. As I stood over the commode jacking my cock I imaged how it would feel to fuck Mandy in the ass. When I came it took five or six forceful streams to empty the cum from my balls. My orgasm exhausted me to the point of having to sit down or fall from my weak knees. I knew right then that I was gonna try and talk Mandy into letting me fuck her in the ass.
That night I put my plan into action. When we went to bed I started the usual fore play and before long we were naked in each others arms. Mandy is passionate and loves sex as much as I do so before long I was enjoying the feel of her mouth as she sucked my cock. Usually she likes to suck me until I cum for her then get me hard again so our session lasts longer for her pleasure.
Tonight I had other plans. I stopped her blow job and went down on her. I really enjoy eating her pussy until it is sloppy wet and she has orgasmed at least once. I got her off one time then slid up her body until my dick was pressing against her crotch. Mandy reached between us and guided me into her. The walls of her pussy were hot on my cock as I penetrated her. I fucked her like that for several minutes with the image of the video filling my head. The wondered of what I was about to do had me on the edge already so I slowed down.
After I calmed myself I pulled out of her and asked her to turn over and get on her knees. Mandy likes it from behind so she readily agreed. When she was in position I imitated the video and stroked my cock through her pussy lips and over her asshole. Mandy didn’t moan like the woman in the video, but she did wiggle her hips as I rubbed my cock through her crotch. She did moan when I slipped my cock into her pussy though. With my hands on her ass cheeks I pumped my cock into her slowly.
When she started asking me to fuck her harder I complied. As I fucked her I watched her asshole anticipating what I was about to do. I pounded her hard and fast for maybe thirty seconds and slowed down again. I decided that was the moment so I wet my finger. I rubbed it on her asshole and pushed the tip into her. Mandy moaned so I got bold and slipped my finger in to the first knuckle. Mandy stopped moving and asked me what I was doing. I told her about watching the video earlier and that I wanted to try anal sex if she would like to try it. That’s when things got surreal. Mandy pulled away from me and lay down on her back. I lay down beside her.
“Okay, if you want to fuck me in the ass you have to let me fuck yours first. I want you to know exactly what it will feel like for me. If you don’t want to let me do you then that is the end of it. We will not be having anal sex. So what do you say now?”
I was taken back a little. I definitely didn’t expect that response. I really wanted to experience fucking Mandy in the ass, but was I ready to let her fuck mine? I had never wondered about fucking an ass much less having mine fucked before watching that video. It had really got me aroused and I certainly wanted to try anal with Mandy, but this was a big step. No one had ever even played with my ass before.
“What do you mean you want me to experience what it will be like for you?”
“I want you to know exactly what it is like to be fucked in the ass. I have had it done to me once before and I swore it would never be done again unless the guy experienced it first. I have to tell you, I did like it after we got started, but if I never experience it again I will be alright with it. So, if you want to continue down this path here’s what we will do. I will get my dildo and use it on you. If you let me do you I will let you do me. You don’t have to decide now. You can think about it and if you still want to do it all you have to do is let me know you are ready to try it.”
Wow. Even the conversation about it was turning me on. My dick was rock hard and throbbing. I didn’t have a clue why, but I really wanted to try this. I made my decision.
“Okay, get your dildo. I’ll let you show me how it feels first. You have a point when you say I should know how it feels. If I don’t like it or it hurts too much I shouldn’t expect you to let me do it to you.”
Mandy rolled over and opened the bedside night stand. She took out her dildo and a tube of KY jelly. Her dildo was about the same size as me. She told me when she bought it that she didn’t want anything enormous. Just something my size so she could satisfy herself when I wasn’t available. We had used it quite often during our sex play too. Mandy loved to suck my dick while I used her dildo to fuck her.
She turned back to me with a smile on her face.
“Here’s the deal. I want you to get on your hands and knees so I can get you ready to take this. I’m going to use my fingers to loosen you up before I put this in you. Are you sure you want to do this?”
Instead of answering her I rolled over and took the position. With my legs spread slightly and my ass in the air I felt totally exposed. My hard cock was pointing straight down. I looked between my arms at it and saw the drop of pre-cum beading on the tip. I saw Mandy’s hand appear from below my balls. She encircled my shaft and spread the drop of pre-cum over the head of my dick with her finger. As she did that I felt her other hand on my ass. Then I felt the coolness of the KY as she pressed a finger against my anus. I was surprised at how good it felt as she circled my anus as she pressed gently. When her finger tip slipped inside me a small moan escaped my lips. It felt even better when Mandy started sliding her finger deeper into me. When she had her whole finger in my ass she asked how it felt. I answered with a moan, letting her know I liked it.
Mandy started sliding her finger in and out of my ass. Before long I felt her adding a second finger. As I felt my sphincter expand to accept the second finger a wave of pleasure washed over me. Mandy was slowly stroking my cock as she used her fingers to fuck my ass. My level of arousal was mounting rapidly now. Within seconds my asshole felt loose around her fingers. Mandy removed her fingers and replaced then with her dildo. I felt the cool jelly as the head of it slipped through my relaxed sphincter. My god did that feel good. I would have never imagined that having something like Mandy’s dildo pushing through my sphincter could feel so good. As inch after inch of her dildo filled my ass I moaned from the erotic pleasure it was giving me. When she had all of it buried in my ass she stopped and asked how it felt.
“Oh my god! I can’t believe how much I like how it felt as you were pushing it in me. Right now I feel so full. Not really uncomfortable at all. I can’t wait to see what it feels like when you start fucking me.”
Mandy was stroking my cock and the feeling of that while my ass was full of her dildo was incredible. She started withdrawing and I could feel it slipping through my stretched sphincter. When only the head remained in me she stopped and changed direction. This time she slid it all into me in one motion. Not stopping until it was completely buried in my ass. Mandy stroked her dildo in and out of my ass as she stroked my cock. She got faster and faster as my moans increased in frequency and volume. I was pushing back on every out stroke, trying to get more of her dick in me. It only took minutes before I felt my orgasm create to the breaking point and I ejaculated all over the sheets below me. Mandy jacked my cock and fucked my ass until I finished cumming. She slowly withdrew the dildo all the way out of me and I suddenly felt the empty void.
“Slide it back in me baby. I want to feel it as it goes in.”
Mandy obliged me and slipped it back in. There was no resistance now. In fact it felt incredible as it entered my ass. I loved the sensation as her dildo filled my ass. She pulled it all the way out and reinserted it several times causing me to moan with each penetration.
“You really like having this shoved in your ass don’t you, Paul? I bet you weren’t expecting that were you?”
“No, I wasn’t expecting that. The feeling is incredible though. You can do that to me anytime you want from now on, but now I want to know what it feels like as my dick slips into your ass. We are going to have to wait a while for that though. My orgasm totally drained me and I don’t know if I can even get hard again tonight.”
“Oh, I think we can get you hard again. Doing that to you and seeing your reaction has got me so turned on that there is no way I am going to sleep without getting off tonight. I am going to suck your dick until it’s hard and then you are going to fuck me. I bet it won’t take three strokes to get me off either. After that you can have my ass if you want it, but right now I need to cum.”
Mandy got on her knees and bent over my waist. She took my flaccid cock in her mouth and fondled my balls as she sucked me. It wasn’t long before her ministrations had my dick stiffening. I could feel it getting hard as less and less fit in her mouth. When I was fully erect again Mandy threw her leg across me and guided my hard dick to her hungry cunt with her hand. As my dick penetrated her wet pussy I could feel the heat. She was right too. It took about a half dozen strokes into her and she was cumming hard. She sat down hard, capturing my fullness inside her. She rocked back and forth rubbing her cervix with the head as she came for what seemed a full minute. When her orgasm subsided she collapsed on top of me and sighed.
“Oh my god, that was fantastic, Paul. If you are ready to fuck my ass I am ready for you.”
I kissed her and rolled her over onto her back. I got between her legs and buried my face in her crotch. Her pussy was wet with her juices and I sucked as much as I could as I tongue fucked her. I used a finger to play with her asshole as she moaned under me. I wet my finger and inserted it in her anus. Mandy moaned and raised her legs giving me more access to her bottom. When I had her loose enough to use two fingers on her I got up and positioned my myself so I could get my dick in her. As the head of my dick touched her asshole Mandy moaned and told me to go slow. I pushed and the head popped inside her. I could feel the tightness of her sphincter around the head of my dick.
I pushed more and a couple inches slid into her ass causing her to moan again. I worked myself in and out of her, letting a little more enter her with each stroke until I was completely in her ass. It felt fantastic. I remembered how good it felt when she buried her dildo in my ass as I began to fuck her. The more aroused I became the more I found myself wishing it was me being fucked instead of fucking. It was over in minutes. My orgasm overtook me and I sprayed her bowels with my cum as my balls emptied.
We lay there with my dick going soft in her ass. “Well, did you like fucking me as much as you liked being fucked?”
“Damn, babe. I can’t decide which I like more. I really am surprised how much I loved your dildo in my ass.”
“I know you liked it and I enjoyed your reaction too. I think we just found something to add to our sexual repertoire. Now let’s get cleaned up so we can get some sleep.”
Two nights later as we were having sex; me on top and buried deep in her wet pussy, Mandy put her hands on my chest and asked me to stop. I held myself fully inside her hot pussy and asked why.
“Because I have been constantly thinking about what we did the other night and it has awakened something in me that I have to talk to you about. I can’t get over how much you liked it when I fucked you with my dildo. Now I can’t stop thinking about how much you might enjoy the real thing. We have talked about my fantasy of having two men at the same time before. I remember how you thought you might like to see me getting fucked. I am thinking that we could kill two birds with one stone if we could find the right guy. I would love to watch you getting fucked in your ass and you could watch me getting fucked too. What do you think about it?”
“Holy shit, Mandy. Are you serious? You really want to bring another man into our bed and have him fuck us both? I mean, yeah, I would love to see you getting fucked and joining in so you could experience two dicks at the same time. As for him fucking me, I don’t know. I did enjoy your dildo, but that was something between us. I need to think about that more before I can give you an answer.”
I realized my dick was still hard inside her and even without moving the conversation was getting me close to cumming. I thought what it would feel like to have a hot dick slipping into my ass as my wife watched and my dick throbbed. I could feel my cum rising so I pulled out and shoved my dick in Mandy’s face. She took it in her mouth just as I started to cum. She moaned as I ejaculated in her mouth. She swallowed my load and kissed me. I could taste my cum on her tongue.
“Okay, mister. You owe me a good pussy licking for that. Get down there and make me cum, baby.”
I did what she demanded and ate her to two climaxes before she begged me to stop because she was so sensitive it hurt to be touched. As I ate her I was thinking about what she had brought up. By the time she stopped me I had decided that I wanted to try letting a man fuck me in the ass. Just the wondered of it had me hard again. I sat up and looked down at Mandy. She was so hot laying there naked and flushed with her orgasms.
“Alright, Mandy. I think we should try to find someone that we both like to join us for a threesome. I really have no idea how to go about it though.”
“Oh goody. I know you will love it as much as I do. As for finding the right guy, I do have someone in mind. Do you remember Jake? The guy at my work that is always talking to you at our company get togethers. I’m not sure, but Darla told me he is gay or bi-sexual. She wasn’t sure which. I think I can talk to him and figure it out if you want me to. Would you be okay with him being the one?”
“He is very friendly with me every time we are together. I like his personality so yeah, he would be okay if he is into guys. I don’t know what to expect because this is all new to me. I’ll trust your judgment on this one.”
The next day at work all I could think about was what if Jake accepted Mandy’s offer. That would mean that come the weekend a man’s dick would be entering my ass and it excited me. That night Mandy told me that she had talked with Jake and he was indeed bi-sexual. He readily agreed to a threesome with us because he had been trying to hit on me ever since we met, but was afraid to be too forward about it. The next day at work was even harder. It was three days until Friday night and our date with Jake. My thoughts kept filling my mind with images of Jake fucking Mandy and then me. My dick stayed semi hard all day. The more I wondered about it the more I wanted to experience his dick entering my asshole as he fucked me. I thought how big he was and if I would be able to take him if he were bigger than Mandy’s dildo.
By Friday I was so horny I could hardly wait for the evening to get here. Finally the work day passed and I was headed home. I took a shower and dressed casually for our date night. Then I waited impatiently for Mandy to get home from work. The hour passed slowly, but it passed. Mandy got home, showered and dressed with a half hour left before we were to leave to meet Jake at our favorite restaurant.
We had a great dinner. The conversation was engaging, but the main subject of the evening was avoided. We all knew what the evening had in store for us later so we got to know each other a little before dinner was over. Jake followed us to our home after dinner. Once in the house and I had fixed us a drink Jake looked at me and asked if I was sure I wanted to continue the evening. I said of course and he turned to Mandy and kissed her; his hands planted on her ass. When he broke the kiss I saw that Mandy’s hand was holding his cock through his pants. The bulge looked enormous.
Mandy looked at me and suggested we take our drinks to the bedroom. She took Jake’s hand and walked down the hall to our room. I followed. My dick growing as we approached the point of no going back. In the bedroom Jake started to undress Mandy. He told me to come help him. As I approached he removed her blouse and unhooked her bra. I got behind her to unsnap and unzip her skirt. As I kneeled to pull her skirt over her hips Jake removed her bra exposing her gorgeous tits. He bent and sucked a nipple into his mouth. Mandy moaned. I let her skirt pool at her feet as I slid her panties down her legs. I kissed her exposed ass cheeks. Mandy turned to face me and I put my face in her crotch. I could smell her juices as they leaked from her pussy. I was eating her pussy and Jake was alternating sucking her tits. Mandy was moaning loudly as we worked her over. I heard her asking Jake to fuck her. I sat back on my heels as he guided her to the bed. She sat on the edge and Jake pushed her onto her back. She lay there as Jake started to undress.