2nd try at anal sex
My sugar daddy and I had agreed do's and don't when we made our arrangement and I was happy with that, what I didn't know was he wasn't, but one day he brought it up, we were in bed after some rather enjoyable sex, just chilling out....
"so, there's something I've been wanting to ask, I know you told me no, but I'm hoping you'd reconsider?" he started
I put my phone down and said "reconsider what?"
"basically? I'd like to have anal sex with you" he said
"I told you I'd tried once and it didn't go well, which is why I'm not keen on it" I replied
"I get that, and a bad experience can put you off for life, but you should try again to decide if you're really not keen," he said "The guy you tried with had no experience and I've had anal sex with a number of women and while some didn't enjoy that much, no-one said it hurt or was painful. It was their first time with 2 girls and they both enjoyed the experience."
"So, you want to try it with me?" I asked
"I'd like you to try, if it's not for you or hurts at all then we can stop and I'll never ask again"
I thought about it and decided to get mercenary. "OK, but only if I get to buy that dress I liked!" I said - we'd seen a dress I wanted earlier but it was out of our agreed budget.
"Babe, let me fuck you up the arse and we'll go get the dress today" he said.
I laughed "oh hell no, we go get my dress, THEN we'll try."
"Deal!" he said and we got dressed.
On our way back from shopping we stopped at the supermarket and he bought coconut oil, he said to me "lubrication, there's all kinds of expensive things you can buy but honestly this is best and long lasting"
So we get back to the hotel and things start happening, and by now my sugar daddy knows how to turn me on so much I can orgasm before him, he purposefully does that and I have a very nice orgasm doggy-style, and then I flop on the bed face down, and then he goes "ok honey, pull your knees up under you and we'll give this a try.
I think to myself oh god this is a mistake, but I'm stil feeling warm and fuzzy from my orgasm so I comply and present my ass to him... now last time I was like this and a guy was trying to butt-fuck me he just pushed so when I felt something touch my anus I tensed up.
"it's ok baby, just relax" he said and continued to run his finger around my ass. Very slowly he pushed his finger into my bum each time.
He kept going and I was still all fuzzy from the orgasm, and then I felt his hard cock against my pussy and he gently pushed himself inside me and kept it there, I like that feeling and then I felt his finger slide about an inch into my bum and I tensed, he felt it and just held his finger still and then moved slowly in and slowly out, after 5 minutes of that I was getting horny again as his hard cock was moving slowly inside me...
I think he could tell because he said "feeling in the mood again?" and I went "hmmmmm"
I felt his finger slide out and then he massaged my anus again, more oil this time and then I felt something larger go into me, his cock was still in my pussy so I said "what..."
He replied "just more fingers sweetie, it's fine..." and carried on slowly.
After a few more minutes he started moving against me cock and fingers slowly going in and out and while it was a little bit weird it was fine and I was enjoying it. then his cock and fingers withdrew and I felt his hard cock against my ass and he gently pushed, I tensed up a bit and he said "just breath out and relax" and so I did and he entered my anus, it felt much bigger then his fingers but not too big, I continued to relax and I felt it go about 1/2 way in.
"there baby, good girl" he said and slowly started moving back and forth, taking it slow, adding a little oil now and then and it was still a little odd but not painful or uncomfortable. This continued for a few minutes and each time he went a little deeper until he slowly stopped inside me and said "how do you feel now?"
"hmmm yeah, it's ok" I replied
"my entire cock is inside you now honey" he said
I was honestly surprised! I didn't think he'd gone that far. Before I would reply he slid out a little and in again, always slow and if I tensed he stopped and said to breath out.
After about 5 minutes he'd managed to get a good rhythm going, not fast but in and out almost all his length, he started gripping my ass harder and going a little faster, but I tensed up and he said "play with your pussy, it'll help you relax" and so I did, it did help and was a very nice feeling, that and his cock inside my backside.
He slowly went faster and I was masturbating quite hard, I felt him shudder and knew he was about to cum, and he quietly said "ooooooh god Lauren" as he came inside me.
I didn't orgasm but he gently withdrew his cock and I lay down, I was expecting his dick to smell or you know, be like brown or something, but it was clean! I didn't get it, but he said later the first section of about 9 inches of intestine is clean so it's not like that.
I turned over and I felt a sudden urge to poop, I dashed to the loo and sat down and I let out a huge wet fart and his cum dripped out my ass, but I didn't poop. I cleaned up and it was a bit fragile, but not at all painful.
Later that evening I asked him who Lauren was, he looked surprised but just said "oh just some girl" I knew I'd shocked him, and he wasn't being honest - this isn't a relationship, I know he's married with k**s so I'm not going to rock the boat, I'm there to make him happy.
After my first experience we did it more and I've now been able to orgasm through anal sex and masturbation and recently (not with him, that's a story for another time) I've had an orgasm through anal sex alone.
"so, there's something I've been wanting to ask, I know you told me no, but I'm hoping you'd reconsider?" he started
I put my phone down and said "reconsider what?"
"basically? I'd like to have anal sex with you" he said
"I told you I'd tried once and it didn't go well, which is why I'm not keen on it" I replied
"I get that, and a bad experience can put you off for life, but you should try again to decide if you're really not keen," he said "The guy you tried with had no experience and I've had anal sex with a number of women and while some didn't enjoy that much, no-one said it hurt or was painful. It was their first time with 2 girls and they both enjoyed the experience."
"So, you want to try it with me?" I asked
"I'd like you to try, if it's not for you or hurts at all then we can stop and I'll never ask again"
I thought about it and decided to get mercenary. "OK, but only if I get to buy that dress I liked!" I said - we'd seen a dress I wanted earlier but it was out of our agreed budget.
"Babe, let me fuck you up the arse and we'll go get the dress today" he said.
I laughed "oh hell no, we go get my dress, THEN we'll try."
"Deal!" he said and we got dressed.
On our way back from shopping we stopped at the supermarket and he bought coconut oil, he said to me "lubrication, there's all kinds of expensive things you can buy but honestly this is best and long lasting"
So we get back to the hotel and things start happening, and by now my sugar daddy knows how to turn me on so much I can orgasm before him, he purposefully does that and I have a very nice orgasm doggy-style, and then I flop on the bed face down, and then he goes "ok honey, pull your knees up under you and we'll give this a try.
I think to myself oh god this is a mistake, but I'm stil feeling warm and fuzzy from my orgasm so I comply and present my ass to him... now last time I was like this and a guy was trying to butt-fuck me he just pushed so when I felt something touch my anus I tensed up.
"it's ok baby, just relax" he said and continued to run his finger around my ass. Very slowly he pushed his finger into my bum each time.
He kept going and I was still all fuzzy from the orgasm, and then I felt his hard cock against my pussy and he gently pushed himself inside me and kept it there, I like that feeling and then I felt his finger slide about an inch into my bum and I tensed, he felt it and just held his finger still and then moved slowly in and slowly out, after 5 minutes of that I was getting horny again as his hard cock was moving slowly inside me...
I think he could tell because he said "feeling in the mood again?" and I went "hmmmmm"
I felt his finger slide out and then he massaged my anus again, more oil this time and then I felt something larger go into me, his cock was still in my pussy so I said "what..."
He replied "just more fingers sweetie, it's fine..." and carried on slowly.
After a few more minutes he started moving against me cock and fingers slowly going in and out and while it was a little bit weird it was fine and I was enjoying it. then his cock and fingers withdrew and I felt his hard cock against my ass and he gently pushed, I tensed up a bit and he said "just breath out and relax" and so I did and he entered my anus, it felt much bigger then his fingers but not too big, I continued to relax and I felt it go about 1/2 way in.
"there baby, good girl" he said and slowly started moving back and forth, taking it slow, adding a little oil now and then and it was still a little odd but not painful or uncomfortable. This continued for a few minutes and each time he went a little deeper until he slowly stopped inside me and said "how do you feel now?"
"hmmm yeah, it's ok" I replied
"my entire cock is inside you now honey" he said
I was honestly surprised! I didn't think he'd gone that far. Before I would reply he slid out a little and in again, always slow and if I tensed he stopped and said to breath out.
After about 5 minutes he'd managed to get a good rhythm going, not fast but in and out almost all his length, he started gripping my ass harder and going a little faster, but I tensed up and he said "play with your pussy, it'll help you relax" and so I did, it did help and was a very nice feeling, that and his cock inside my backside.
He slowly went faster and I was masturbating quite hard, I felt him shudder and knew he was about to cum, and he quietly said "ooooooh god Lauren" as he came inside me.
I didn't orgasm but he gently withdrew his cock and I lay down, I was expecting his dick to smell or you know, be like brown or something, but it was clean! I didn't get it, but he said later the first section of about 9 inches of intestine is clean so it's not like that.
I turned over and I felt a sudden urge to poop, I dashed to the loo and sat down and I let out a huge wet fart and his cum dripped out my ass, but I didn't poop. I cleaned up and it was a bit fragile, but not at all painful.
Later that evening I asked him who Lauren was, he looked surprised but just said "oh just some girl" I knew I'd shocked him, and he wasn't being honest - this isn't a relationship, I know he's married with k**s so I'm not going to rock the boat, I'm there to make him happy.
After my first experience we did it more and I've now been able to orgasm through anal sex and masturbation and recently (not with him, that's a story for another time) I've had an orgasm through anal sex alone.
4年前
