What was your first time having anal sex like?

I had a boyfriend at age11. My parents tried to forbids me but I wanted a boyfrien . It didn't help that he was 14. His name was Vinny. One day we were making out and what little boobs I had he was rubbing. I'll never forget how turned on I was.

He brought up fucking me I was terrified so kept saying no. He told me he knew a way and no channce I'd get pregnant. I said yes. When he told me to take my pants and panties off I thought I'd die of embarrassmen . But when I did he had to help me I was so scare . I still had no idea what he was going to do. I got on all 4 s. Like he said and waited.

Next thing I know he's touching my butt hole and spitting on it. I thought it was gross but was so excited and so scared I kept quite. Next thing I know he's pushing something big into me and oh boy did it hurt. I didn't want to be a baby so I said nothing. After like eternity he pushed more in and pain was so bad. Then he started in and out. I was not happy.

After he came in my ass he asked me to clean him I wouldn't. We dated for about 2 months then he dumped me for another girl. He then told all boys about my ass. I was so humiliate . Years later I met a young man who helped me to enjoy it and now its my favorite

@Megansrear this guy Vinny was a creep and you are better off without him because what he did was just wrong. It is good that you met somebody you liked a lot better and treated you right.

My first time was with my wife. We had been together about a year when I ventured a little further south with my tongue as I was performing oral sex on her. She seemed to enjoy the rim jobs I would give her. After some time I started pushing my tongue on her hole; but, I never really penetrated it. Nonetheless, the licking and pushing with my tongue on her hole definitely got the desired reaction. Realizing she enjoyed anal stimulation, it didn't take long before I was inserting a finger in her ass as I licked and sucked on her pussy. I suspect this went on for several years before we had true anal sex with my penis penetrating her ass. We did this in a spooning position. It did not get the desired reaction from her and we never tried it again. I believe her greatest sexual pleasure was always derived from my tongue on/in her pussy and that was impossible to accomplish with my dick in her ass. However, realizing she did enjoy a finger in her ass, I bought a small butt plug on one of my road trips for business to see what my reaction might be to anal stimulation. While I doubt I'd even feel that thing in me now, that was the start of my continuing adventure of pleasuring myself anally. Holding a dong fully in my ass, pumping a toy in and out, and stretching my hole have become the sexual joys I look forward to almost every day.

Was15 my and friend like to go night fish so this night I said do you want to fuck me up the ass he said OK so we ended up fuck even time fish like love be the first one to pull off my pants for my mate to fuck me till he cumming inside my I fuck him till my cumming in him did it for 2yrs

Around 14 I did it first time myself with fingers. The first pushing did hurt, and the feelings was mixed with both pain and pleasure. Next time I used coconut oil and the experience was great. So would say lubricants are always a great help for anal sex pleasure.

Some five years ago I was in relationship with a girl who was 20 years old. We have regularly had sex, but as regards anal sex, I have long urged and begged to try but did not match with that I did not have the luck to try until one night we got drunk at a party and she came home with me. She had her back to me in bed and I'm like every time slowly from behind shoved my dick into her vagina, pulled it out of her vagina and slowly put it in the ass. She was shivered, but I continued while I did not cum in ass. It looked something like this http://porn18videos.com/vid/teen_anal_fuck_hardcore_asshole_fuck . This is she`s first anal sex experience. Every next time she demanded that I have sex with her in the ass😉

I was 15 and had my first date with a boy I had a terrible crush on. We went to s movie and then found a secluded spot in the park and made out for a while. We went to his house since I was spending the night. We rushed to his room and into bed for sex. It was a bit awkward since I didn't know what to do, but my friend helped me out and while it hurt at first and I was scared but it turned out to be pleasurable. With a little practice, I got to love it.

The first time was a little bit awkward and a little painful, but not too bad to make the experience bad. And since I've always been very anal erotic, that awkward/slightly painful encounter was still amazing to me and left me wanting more. It was definitely better the next time and each time after that.

My first time was when I was 18. It was very painful and I really regretted it. I have had enjoyable experiences since but with a different man.

Never had it , gave it twice.

Sticking small objects like pencils, as a child, very young, 4, 5, or 6. But my first with a partner was exciting and sensual and fun. So very dirty. (Taboo)

It was my live in partner, we had abdsm relationship and he, after playing with my anus and lube etc., he took me. Bent over the edge of the bed, hands tied. It was a great memory.

Been extremely fortunate with first time sexual partners on oral, anal, regular vag intercourse.

I'll try to keep it short. While still a virgin, I enjoyed playing with my own ass. At 16 years old, at a party at my house, a guy I sorta knew asked me to come into the bathroom with him. He asked if I'd blow him. No, but I told him he could fuck my ass. Butt in the air, my head on the toilet seat, he went in with just spit as lube. It hurt like hell, yet somehow I knew this was the beginning of something good. After everyone went home we did it a few more times (bless teenagers) with some Nivea hand cream, which was much better. That was 1976, and I never stopped loving anal.

I've played with my ass my whole life. I've inserted everything I could find in me for pleasure. I've always imagined the real thing in me but never acted on it until about two years ago. I met a guy and we started talking about it and I decided to try it. He was about five inches and thin. He slipped in easily but because of my experimenting I hardly felt him. I was really disappointed.

I shared my experience with a. Lose friend who I thought was as straight as an arrow and he told me that he occasionally topped for guys. I was shocked but we were soon naked and he was thrusting inside of me. He was about six inches but nice and thick. I loved the feeling and knew I was hooked. Unfortunately we have not had a chance to repeat as our schedules don't allow us to get together but I'm hoping that changes soon.

I have enjoyed anal play all my life it seems. As a teen I liked to take my temperature rectally or played with pens and other objects in my bottom. When I started dating and having sex I did not dare tell any of the guys what I really liked so it was vanilla sex all the time, which is not supposed to imply that all the sex I had was bad or unfulfilling.

Two years ago I met a guy online in a spanking chat who told me after some time that he would like to have anal sex with me after spanking me. I thought, "Finally!!", and said, "Ok, I think I could try that."

Before we met he told me to wear different-sized butt plugs to prepare my bottom for his cock. When we finally met, he was really careful, used lots of lube and took his time to stretch me with his fingers and different plugs before we actually had anal sex.

My first experience with anal sex was a really good, very sensual one, it did not really hurt and I am very thankful for that first time.

It was horrible! I felt like I had to expel. I hated it! Since then, my anal hole turned out to be a second pussy. There's a fire that needs to be watered. I have since come to love anal sex. I crave it!

I was 19 (2009) I answered an online ad.For a house boy.I was mailed a bus ticket to North Carolina,after we both agreed for me to start my new life as his house boy on july sixth 2009.I knew that I was going to have to be a bottom,and it happened on july 23rd 2009.We were in Myrtle Beach.I will never forget how badly it hurt(he is hung)But I grinned and took it.We did that again,later that day.I was still well lubed(from the huge load inside my butt.)And I was starting to like it-and did like it so much,that I came all over Dan/Daddy as I rode on the stiff woody.So am now enjoy each time we mate(as he say's)I also enjoy role play with him & my new friend's too!

Never had anal sex.. reading blogs makes me want to try it and enjoy. Used items and fingers, butt not the same. any LA man or woman can call..,hopping to give as well as receive........

I'm a crossdresser. A female friend knew and introduced me to some friends of hers at a club one night. I was in ladies wear and he was interested. Went home with him where his roommates were having a small party. I quickly prepped and was ready for him. (Plenty of self pleasure had taught me much already)

We went into his room and started by giving him oral. Then he got behind me and went to it. While he was doing me the door opened. The house party found us. I ended up with my first time being a 23 guy gangbang with double and triple penetrations. I analgasmed more than I ever thought was possible. I'm certain that all of them had at least 3 or more turns with me leaving a deposit of their semen in me each time. I fell in love with it and have often had multiple partners at the same time since.

Again I was a sophmore in college when one night my boyfriend began playing with my butt when he took his finger and began to circle my anus. I began to squirm and told him I liked that to which a couple of nights later he was back when I told him to put his finger in which he did using all we had Vaseline. I really enjoyed that and a couple of days later, I told him to put his dick in, we did using Vaseline and while it hurt, I told him just to lay on top of me and not move.

I picked up some KY at the drug store and we tried again with him putting it in and just lying still. Yes it hurt but it felt good and it was a nice hurt.. Finally, a couple of nights later I told him to put it in, then begin moving around very slowly to let me adjust and eventually we began doing it.

Had he been a bull in a china shop, I am sure I would have had anal sex only one time. He was slow and easy, did as I said and that is why it worked out for us.

When I was raped in the hospital and I had an anal bleed for two weeks . But later on in this life I quite enjoy a good strap on it brings me to orgasm.

Cowboy!!!

The only thing I can think about what happened to you ...if it was me ... think about an old Hal Robins book "The Carpet Baggers" and a Character "Nevada Smith" and what he did to the men who killed his parents!!

Nuff said!!

Never mind the Kinky Klick, the next one you hear will be the klick

of the 12 Ga. Double barrel shot gun as the hamers get pulled back!!

highwater

@josh: What Is a house boy?

When I was raped in the hospital and I had an anal bleed for two weeks . But later on in this life I quite enjoy a good strap on it brings me to orgasm.

OH NO Cowboy!!!! I'm so sorry to hear that 😢

I guess not yet having experienced anal set is is something to look forward to with that special person for the first time. I have heard it is very painful the first time receiving anal sex and I have heard it is not painful the first time if the man knows what he is doing and is considerate. I am 24 and I feel it will not be long off before I do experience my first anal sex.

Kathy

Since you are talking about an involuntary muscle group and an atypical action for it, the issue (outside of much, much lube) is letting the natural tension of both the external and internal sphincters pass and relax without force. If the partner just "plows on through" there can, indeed, be undue pain. And pain begets tension, which causes portals to spasm, which causes more pain. With a sensitive partner he can be attuned to your body's responses and wait for initial tensions to pass and relaxation to occur before advancing gently further. This leaves any pain as slight stretching, fullness and mild discomfort, giving way to wonderful pleasures. If he is to rough it only brings pain and more pain. That's no good for you. Slow and gentle will be the keys for you and your partner. The door to enjoyment that you can unlock will be well worth the effort. Play nice.

I was 19 years old. It hurt a bit at first, but my boyfriend went slower and it became pleasurable. As long as he stretched me out first with his fingers, I enjoyed it most of the time. He first inserted just one finger until I was used to it...then two fingers, then three. I definitely enjoyed the stretching out process. ?

I wanted to have anal sex with girls from the time I was 12 or 13. I just always loved the curve of their hips and cheeks and the smooth soft skin... and the dirt little secret that was contained within! I was probably 21 at the time with a long term GF where it was long distance as well (being away at college.)

It was a process to get started with anal. We had each only had one (limited) partner before and I first broached my intention to play with her ass after we had had sex on her parents couch. We were lying there with her on top of me and I cupped and stroked her buttocks as we kissed and talked. I slid my hand between her cheeks and slowly stroked her asshole as I said 'I can't wait to explore ALL of you!' Nothing more was said or done that night, but she later told me it 'freaked her out!'

A few months later we got a motel room to screw all day - she lived at home and couldn't stay out all night. I had bought a small jar of vaseline and hid it in a bag or something. We had sex a lot and she was a pretty easy cummer so we just kept switching around what we were doing. I started with my plan to have her lay down on her stomach and I massaged her back and legs and butt. Eventually I was spreading her cheeks and touching her hole, massaging her gently. She knew what I was up to but let me continue. I awkwardly reached for the vaseline hoping I didn't break the mood and have her rebel and get up, but she didn't. I used some to massage more and slowly penetrate her ass, eventually working my whole finger in. I poked around and I think we also had a vibe working on her clit, or maybe she just used her fingers. Anyway, she worked up to a very strong orgasm with me probing her deeply and finger fucking her cute little ass. Later on when we talked about that day, I asked what was her best orgasm out of the 10 or 12 she had and she mentioned THAT one! I was in heaven hearing that!

In another few months I had my sisters house alone for a few days when they went away. My GF came over and she lied to parents in order to spend one over night with me. So on my sisters waterbed ( who is a VERY religious person ) that night we tried anal sex. After thoroughly probing and loosening her up I worked my way inside slowly, waiting for her to accept me. I don't think I moved much at all that first time, but OMG did it feel so good, just holding myself inside of her, feeling her tightly squeeze me! She didn't cum, and even told me later that the first time hurt a bit even though I went so slow. I asked her why she let me do it again and she said that vaginal sex hurt the first time too, and that sure got better, so why not with anal?!

From then on we had anal probably 50/50 with vaginal sex and we'd play with her clit to have her cum during it. I've been addicted to it ever since.

Sorry for the longer story, but those are some fond memories...

I have had some anal play from the time I was married. I liked it, but he never penetrated me there. Then fast forward a lot of years, I had a dom. He played and stretched me out there, but still could never penetrate. It was fun and very erotic and I loved it.

Then this past May (2017), I got to meet a fellow zity member here. He wanted to try. I was nervous about it but still I let him try. I knew it would be fun either way, if he got in or not. We had talked about it on skype a lot and he had said that he would use a whole lot of lube to make it easier. When we did it, he used a lot of lube and then he also used these ice cold glass anal dilators to stretch me out before he actually tried to penetrate me. The cold glass soothed the pain from the stretching, and of course, they also felt very good. They did the trick and he was able to get in. It felt so good!!

I can't wait for October!! We get to see each other again!!

I had anal sex when I was around 24. It really hurt! He was very large and I think there wasn't enough lube. Plus, I had never done that so I wasn't stretched out. I don't really regret it but I wish I had known more about sex. Now, I love anal play but still haven't gotten to have actual anal sex. I really want it though.

My ex husband tried a few times but he was rough and didn't do anything to prepare me - anything - so it never happened. It was like "ouch! No! Done!"

Fast forward a bunch of years and my current husband is massaging my back (we were still dating). He was straddling me, we were both nude and his cock was rubbing between my cheeks in a delightful way. We were pretty oiled up and it was pushing on my anus and it felt really good and it just kind of creeped in there a millimeter at a time. He asked me if I wanted him to stop and I said no it feels good and it did. Before you know it he was in me and it only hurt a little. I held a vibe on my clit and he started thrusting gently and it was awesome. I came hard it's now one of our many fun time activities- and I was a "nope no way" girl before him. It's all about the right partner. So at like 48 I found I still had some virginity to lose and I'm very glad I did!