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Sex Stories: Diary of my affairs. Chapter 5. My first anal experience
For those who haven’t read chapters 1 to 4 at this time here’s a little catch up first. I ended chapter 4 with the first time I blew my future husband Wayne while working as a barmaid at a local bar/poolhall where we hung out and getting my first ever taste of cum. After finding out Wayne and I were both interested in being more than just friends we had sex of some kind practically every day like we were trying to make up for lost time. It was anything from blowjobs when I was on my period to all day long Saturday marathons. Wayne never used a condom and always pulled out mostly cumming on my stomach or back. I’d only let him cum on my face in the shower for a long time after he gave me an unexpected facial that first time I blew him that I covered in chapter 4. The only times he didn’t pull out was when I was sucking him. He loves cumming in my mouth just as much as I love getting my pussy ate. At the time we were probably leading the world in oral sex scenes and did way more oral than actual fucking. Now on to the new. After about a month of fucking and sucking like nymphomaniacs I found out a few things. Wayne was like my first boyfriend Bob in the fact that he liked for me to squeeze his balls, sometimes as hard as I could but very quickly. He also liked for me to bite his dick but not as hard as I could. I also started noticing a jealous streak in Wayne. Every time he’d see me talking to a guy he would start asking questions. He never really got upset always asking in a nonchalant kind of way but I noticed and was actually happy knowing he was jealous. After I admitted to Wayne that he was the first guy to ever cum in my mouth he started asking about my past sex life wanting to know who I’d fucked and what I’d done but I refused to answer. I’d learn years later it was a turn on for Wayne to hear about these things but at the time I didn’t enjoy telling him especially going into details of who, how, when, where and how many times. Sometimes it pissed me off and I’d tell him it was none of his business. One night we were at Wayne’s and I started giving him a blowjob and he asked for anal saying he wanted to cum inside of me. I told him to put on a condom and cum in my pussy but he said it wasn’t the same. I told him I didn’t want to do it and he asked if I’d ever been fucked in the ass before. I didn’t answer so he asked again and I rose up asking him if he wanted me to suck him or talk to him. He said if I’d talk to him he’d eat me instead. It was the first time I ever talked to him about any of my previous sex affairs. Wanting still to keep as much of my past sex life to myself as possible while he ate me I told him that only one of my old boyfriends tried it but it hurt too much. He kept trying to get more information asking about it and I finally told him that at the most my old boyfriend may have got the head in my ass before I jumped away in pain. He asked who it was but I wouldn’t tell him until a few years later. I remember telling Wayne how my old boyfriend was so proud of his dick that the first time I fucked him he had me measure his dick and how he was just over 9 inches long. Wayne said that was probably why it hurt so much and I told him that my old boyfriend Joe (I refused to mention his name to Wayne at the time) may have been longer but Joe’s dick wasn’t any fatter than his. Wayne asked if we used any lubrication and I told him no. He asked about other things I did with other boyfriends but I refused to tell him anything other than about Joe. I told him how I deepthroated Joe hard one time hanging my head over the end of a couch and Wayne didn’t believe me at first but liked hearing about it. Wayne kept saying he wanted to cum inside me instead of shooting all over me and fucking air or his hand when he got off and that Vaseline would help. I finally agreed to let Wayne try it but told him he’d better eat me off before and after and make it worth my while. Naturally he agreed but said if he goy his dick in my ass and I stopped him before he finished he’d get pissed off. I reluctantly agreed knowing that if the Vaseline helped him get in my ass that I was in for a full assfucking until he was done. After draining my pussy dry a few times he said he wanted to watch me suck the dick that was going to assfuck me. As I sucked him he asked me a bunch of questions wanting me to bite if the answer was yes. He said how it would be a lot easier with the Vaseline and I was hoping he was right. The last question he asked was if I was ready and feeling horny and hoping Wayne was right about the Vaseline I bit him hard hoping my assfucking wasn’t painful. Wayne grabbed his jar of Vaseline as I watched him rubbing his dick in it. He got me on the bed with my feet hanging over the edge in doggie style spreading my knees apart and lowering me until he said we were lined up. I felt his dick touch the opening of my asshole followed by him trying to push it in. It hurt and I jumped away a few times before he finally got the head in my ass. When he got that far without me jumping away he stopped to let me get used to it and said he was going to fill my ass with cum. It felt weird to say the least and after a minute or two I felt him slowly pushing his dick farther and farther in knowing I was about to get assfucked for the first time. I asked him a few times to stop and hold it there and he did but he never backed any of it out until he was balls deep in my ass. Once he was all the way in he started talking dirty and said how much he was enjoying the view of his dick in my ass. He left it there for a minute or two before he started slowly going in and out saying how good it felt making love to my ass. I thought to myself maybe it feels good to him but my first assfucking wasn’t doing anything for me and it still hurt. I was hoping he’d get off quick and get it over with and was almost in tears from the pain I was going through just to satisfy his wish of cumming inside of me. Every time he went balls deep I would grimace and moan while clenching my teeth. I almost told him to stop it altogether a few times but knew it would piss him off and only asked him to slow down or hold it a few times pretty much letting him do his thing trying and not to bitch about it. Later he would speed his pace up for a while only to slow down again and kept telling me how tight my ass was. I hadn’t came anywhere near close to cumming and was actually more turned off by getting assfucked than turned on by it. Although after a while I wasn’t in as much pain as I was at first I wasn’t anywhere near comfortable either. Finally he said he was close to cumming and started drilling me faster as I moaned. It hurt and I would have asked him to slow down but knowing he was close I wanted him to hurry up and cum in my ass and get it over with. The next thing I knew he had his hands wrapped under me a little on the sides of my stomach and he was thrusting forward while pulling my hips to him going back and forth in my ass as hard and fast as he could go asking me if I was ready for him to cum in my ass. Of course I said yes as I kept hearing the sound of his balls slapping against my pussy with every stroke. When Wayne first started he said he was making love to my ass but he sure as hell wasn’t now. He was fucking my ass now and setting it on fire drilling me as fast and hard as he could go. I kept moaning out loud in pain and he kept on plowing away never once asking if I was ok. He was on a mission to cum in my ass and I knew he was going to keep pounding me until he was through. Then Wayne pulled my hips to him hard and held them there as he shoved it all in leaving it there and let out a loud moan as I felt him cumming in my ass as deep as his dick could shoot. My first assfucking was finally over with and I felt so relieved when he was done and went straight to the bathroom trying to lose some of Wayne’s load. When I returned he asked if I was ok and I said yes but not to plan on getting anal again anytime soon. I made him eat me again and he did but once I got off he started to climb on top of me to fuck me. I told him no, not yet saying after what he just put me through he was going to eat me until I decided I was ready to fuck. I purposely made him eat me off a few times until I was tired of hearing him beg to fuck me. Wayne had quite a few other times where he asked for anal offering that I could be on top and in control but I always refused telling him to put on a condom and cum in my pussy. He offered to pay for my prescription if I’d go on the pill but I declined. About a month before my birthday Wayne asked if I’d like to go on a vacation to celebrate it and I said I would if I could get off work. It didn’t hit me right away but once I remembered that he was planning on proposing to his old girlfriend Debbie on her birthday I got excited. Luckily for me they broke up a few weeks before her birthday. We were in love with each other and I was prepared to say yes thinking he might propose while we were on vacation. Even though we’d only been dating for a few months we’d known each other for about three years and marrying Wayne did cross my mind a few times but I didn’t know if he ever thought about it. As it turned out it was him who couldn’t get off work but just for a week. The very first night on vacation we were in the hotel fucking with him on top of me and he said he was ready to cum and I was real close to cumming too and told him not to stop and wrapped my legs and arms around him not wanting to let him go knowing I was taking a risk of getting pregnant. I’ll never forget the conversation that followed. While continuing to fuck me Wayne asked if I’d marry him and in the heat of the moment I said yes. Wayne started drilling my pussy even harder and when I felt his warm cum filling my pussy it sent me over the edge and I started cumming like crazy. I always imagined being proposed to me by a guy on his knees and not fucking me at the time. As it turned out I didn’t get pregnant, at least not that time and the next day we were off shopping for wedding rings and eloped a few days later while we were there. My next chapter will be about the next time I gave up anal to Wayne. It didn’t happen until after we’d been married for a few months. Thanks for reading Mary
See also other stories on: anal sex, blowjobs, couple, getting pregnant, girl, oral sex, pregnant, sex.
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