First time you had anal sex

[wallaboi]

I was 18 when I first got fucked. Was travelling by myself and met this really hot older guy about 42yrs, who invited me to stay at his place. We spent a couple of days making out and exploring each others bodies, sucking and rubbing our hard cocks and bodies together. About the third day he told me to lay on my side coz he wanted to fuck me. I did so with some aprehension, but I had come to trust and I liked him very much. He lubed his cock and my anus and massaged my hole for quite some time with the head of his cock. Eventually I relaxed enough and he popped the head of his cock through my hole...WOW it felt awesome! Slowly he pushed his shaft deeper into my arse and I don't know how to describe the feeling...the pressure was slightly painful, but I really liked this guy and I could feel his hot throbbing cock inside me. At tihis time I thought I was in love and I wanted him to get his cock as deep into my body as possible. I pushed my arse back and felt his cock reach what i thought was the depth of my insides. He started to slide his cock backwards and forwards in my arse...it was a completely new experience, both uncomfortable and sexy as hell. My cock was hard as hell. Each time he thrust deeper and deeper and I could feel his cock hit the wall of my insides. By this time I had my hand down there and I knew there was at least a couple of inches of his cock that wasn't going inside me yet. After thrusting away for a while he came to rest. He kissed and sucked my neck and breathed heavily in my ear. His hands were all over my body and he stroked my cock. He made his cock pulse in my arse. He breathed and licked and whispered into my ear "I want to get into the second door...I want to get my dick into you as deep as I can...relax and push like you gonna shit." He pushed hard and deep and my rectum began to open. The pain was searing, but he sank the full length of his cock in my arse. I gasped and every nerve in my body was jangling. He paused to let me catch my breath with his cock buried deep and then began the pounding. It seemed like quite a while I got pounded, and then his cock and body went into wild convulsions as he came in me. I can still feel the throbbing of his cock and warm flood of his cum.

 

[B_TalkingHeads]

I was 18.

 

[D_Andy_Whorewall]

14, maybe 15 with a neighbor. We had been experimenting for a few years getting more bold as we got older. Rubbing each other's cocks, then jerking each other off, then sucking on each others cocks. We talked about anal as the next forbidden act.

I decided to try it first. We were in our basement after school. It was cool and damp and we had already shared many encounters there. I had a jar of vaseline ready. We dropped our pants and our erections sprang to life, his much thicker than mine.

He globbed the vaseline onto the head of his cock as I stood up against a closet door with my hands outreached and my virgin ass pushed out for him. I could feel the head of his cock poke around a few times, here and there, often sliding down below my anus.

I reached back and put the head of his cock right up to my hole, then he pushed. It didn't seem too bad, so I pushed back onto him. Lightning struck every nerve in my body as soon as his entire head poped in !!! I was breathing heavy and started to sweat. Within a minute the spasms in my rectum subsided and I pushed back more.

The pain level increased, but not as bad. He began short strokes just out of instinct. Soon I opened up enough and relaxed to now feel the full length and girth of his cock fill my virgin ass. Before long his entire cock was inside me. I could feel it pushing up into my body and a feeling of euphoria started to come over me.

All of a sudden he began jerking and groaning and he grabbed my hips and pounded away like a battering ram. As he came, he actually lifted me up with is heavy pounding, untill finaly he was done.

He pulled out after a few moments. He was still hard as a rock, his cock all red and shiny from it's new adventure. Soon cum came rolling out of my ass, all hot and gooey. He didn't think I'd let him fuck me as he did...he figured it'd hurt to much after the head went in and I'd chicken out.

We had a few more sessions during the next year of hot anal sex, and a mix of oral as well. Great times experimenting with a good friend...to this day, the best times I've had. No regrets.

 

[joeweekend]

New Year's Eve, 1979 into '80. My friend James (who, several years before, had taken my virgin mouth, too). We were drunk. And he'd apparently been wanting to do my ass for a long time. (Writing this, I can't think why it took so long. We'd been fooling around since age 13, and I was 19 at that point.)

He did me lying face down, though I recall my head being up against he pillows and the headboard. We used lots of lube, and James loosened me up patiently with his fingers. Yeah, it hurt like hell when he entered me, but I got used to it fast. That, and he has a totally average size cock. His careful preparation of my ass paid off because it was some of the best sex I ever had. The sensation of being filled up like that was magnificent. And when he came, and filled my up with his own lube, it was even better.

Minutes later, we flipped, and I fucked his well practiced ass. Also a first for me. What a night . . . .

Advice to those who've never been fucked: make sure the guy who's doing you has been fucked himself. Repeatedly. James was then (and remains) a total slut. And he knew how it oughta be done the first time: slowly, patiently and with a boatload of lube and a lot of affection.

 

[B_willy5904]

Ah the first time I was penetrated....
I was in college and was dating a girl that was obsessed with having group sex. When I first started sleeping with her I introduced her to anal sex. She loved it and could not get enough to it. That first night she grabbed a small dildo and did her pussy while I worked her ass. She eventually moved up to vibrators and dildos that rivaled me in size.

One night we were out partying at a bar with some friends. One of the guys was too high to go home, so he came home with us. My gal had a Murphy bed in the living room and I pulled it down for him to crash. We went to bed and started a marathon session of sex. After we had anal sex, where she had used big red on her puss, I suggested that she might want the real thing. She smiled at me and said how. I suggested that we had been so loud that Irv must be lying in bed masturbating to the sounds of us fucking.

Lisa got up and marched right out to check it out. Sure enough Irv was lying in the Murphy bed wacking it off. Lisa stopped him and climbed on top of him to work her magic. Soon I was in bed with them, for the next hour or so Irv and I double penetrated Lisa until she could take it no more.

Lisa said she needed a rest, but it was obvious that Irv and I had no need to stop. She said that if we wanted to continue with her, we needed to put on a show for her. She wanted to watch Irv and I have sex. Without much thought of it we dropped into a sixty-nine and sucked each other off. I then put Irv on his back fucked his virgin ass. We then switched around and he lubed me up and fucked my hard. I enjoyed it a lot. After that the three of us continued to fuck each other for the rest of the weekend in Lisa's apartment. Irv and I fucked each other almost as much as we fucked Lisa.

Irv became a regular partner for Lisa and I. We it came to group sex there was only one rule, enjoy everyone, and make the feel great. We ended up expanding our circle of group sex friends to include Lisa's best friend, 2 other couples for school, Irv's brother, and their very hung cousin. He was the first guy that was huge to ever give it to me, but that is another story.

 

[Rugbypup]

Am still waiting... sigh.

 

[D_Sedwell Biggbottem]

I am still waiting. Hopefully not much longer. Any offers?

 

[1NiceRod]

I was 16 or 17 the first time I was penetrated. He was 18. We were good friends and had been messsing around since I was 12 (oral, jo, etc). We would slide our cocks between each other's legs to simulate fucking. My parents left town for a week one time and they were glad that he could sleep over so that I wasn't alone the entire week. The had no idea the things we had been doing. Anyway, we were in bed and he was fucking between my legs and he was having a hard time getting to the point where he could cum. I was feeling bad for him. I don't know what possessed meto say it, but I said "do you want to try sticking it inside of me?" He stopped thrusting his hips looked and me and asked "Really? Are you sure?" and I said "Yeah, I'm sure." I was already laying on my back. I brought my knees up as the took his cock in his hand and aimed it at my hole. Without any lube, other than the sweat we had worked up, he slid right in. All 7 inches of it. There was no pain at all. We were both in heaven and it didn't take long before he shot his load in my ass. This happened back before AIDS was talked about. We were both virgins except for what we had done together, so there was no concern about STDs. It this were to happen today, there would definitely be condoms involved. From that moment we were hooked and would find some way to get together for anal at least once a week. I tried to fuck his ass once, but he screemed in pain and begged me to take it out. I hadn't even popped my cock head past his tight ring, and we were even using lube. Guess I was already a large dick boy by then.

My first successful penetration of another guy's ass was my freshman room mate in college. He was really horny one night and was fondling his dick while studying on his bed. He was doing it "on the sly" but obviously hoping I would notice - which I did. When he knew I saw him and didn't leave, he came over to my bed where I was studying for a chemistry exam and started groping at my crotch. It progressed into kissing and sucking and then he said he wanted me to fuck him. Still no condom use, but we did use some handcream for lube (only thing we could find). After I shot my load in his ass he went to the restroom to clean out. I had fallen asleep by the time he came back. About a week later he was waking me up at 3 am wanting to know if he could fuck me. I had been dating a girl at the time and felt guilty as hell that I had cheated on her. I told him this and told him that I didn't want to do anything else with him. He was disappointed and pissed but he didn't push it any further.

 

[dombear]

Lets see, first penetration type of experience was my 'god parents' son. I was about 10, and I was copying what I saw in my brother's porn movies... I cannot tell if the penetration led to sex, it was more fooling around. As for real penetration, I was 26, and I was as nervous as anything.

He had an average cock, and it was doggy style with my face buried in the pillow. He essentially just shoved it in, and the pain was unbearable, but I just put up with it, and he proceded to slam fuck me as hard as he possibly could, blew, then walked off... I bled a bit for the rest of the day, and it wasn't until a few guys later that I started to make sure my needs were met too...

 

[hanginglowww]

My first time wasn't as interesting or eventful as some previous ones But here it is:

My first time only lasted for about a minute... but we did stop, rested, then tried again - for a few more times. I just couldn't handle the pain. He was 8 inches uncut, and quite thick... but that wasn't the problem. With enough lube, he slipped in after a few attempts... I just couldn't go on because my ass felt like it was on fire.
I was 16. He was about 40 years older than me. I met him online... He was nice, but I do regret it.

I made the same mistake. I was in my late teens and he was in his mid 50s. He was very kind and gentle and we talked about it for awhile but I was always too scared because he was huge 10inches uncut and thick. I could barely suck him pass his big head. So he finally convinced me to let him. I knew it would hurt but I thought it wouldn't be that bad because he was really a nice guy in person and was quite the opposite in bed. He was an animal and it was the most painful experience ever. Unlike you I did not have the option to stop. When I begged for him to stop he just kept saying I have to get used to it and it would feel better. He was big and stocky guy so I had to lay there and take it.

 

[MrToolhung]

I made the same mistake. I was in my late teens and he was in his mid 50s. He was very kind and gentle and we talked about it for awhile but I was always too scared because he was huge 10inches uncut and thick. I could barely suck him pass his big head. So he finally convinced me to let him. I knew it would hurt but I thought it wouldn't be that bad because he was really a nice guy in person and was quite the opposite in bed. He was an animal and it was the most painful experience ever. Unlike you I did not have the option to stop. When I begged for him to stop he just kept saying I have to get used to it and it would feel better. He was big and stocky guy so I had to lay there and take it.

Sounds very similar to what happened to me. Although he was not 50 and did not have a big cock at all. It was painful and I know I had tears. I asked him to stop but he also said I would I get used to it. After he was done I called up a friend of mine who is an older gentlemen and told him what took place. He called the guy up and gave him hell! And he even told his bf what happened.

 

[hanginglowww]

Sounds very similar to what happened to me. Although he was not 50 and did not have a big cock at all. It was painful and I know I had tears. I asked him to stop but he also said I would I get used to it. After he was done I called up a friend of mine who is an older gentlemen and told him what took place. He called the guy up and gave him hell! And he even told his bf what happened.

Yeah, I had my share of tears also. I almost him left him after that night but I decided to give it one more shot. I was sucking him off for months prior to the first time we tried anal, so I think he was too excited. It continued to hurt but after a couple of weeks I learned how to relax and enjoy it : )

 

[honeydew]

OMG!!! Italianshowoff. You have an amazing bod, all over!!!! Your the kinda guy I dream of.

 

[red7.5]

When I was 15 I tried to let my jo/bj buddy fuck me, but after about 2 inches and 5 minutes, I called it quits (he was pretty damn thick). When I was 20, my 18 yo old boyfriend really fucked me for the first time. He had a longish cock, but pretty thin so it was a fairly easy, pain-free, bareback, lube-free first-fuck (he did rim me - also a first - and prepped me with his fingers).

 

[ChuckNLA]

I was 22 and was picked up by a guy in an adult book store. We saw eachother off and on for over a month and then he had me spend the night and I knew what he wanted. I was lucky as he was not that big, but I never got to watch him fuck me cause he always kept the lights off. His name was Patrick and he was in his mid 30's, older guy (to me at least) who knew how to work the younger guys. Their was no pain, just a little discomfort and then the pleasure of being fucked. Hot damn, that was fun.
Now, I like to watch myself get fucked good and hard.....

 

[guy961]

I was about 22, was with my first bf at the time. Didn't like it the first time, but i fucked him after. Tried it a couple of more times and started to get into it. But really got to it around my 30's and been a big bttm since then.

 

[B_MatureHungDad]

I was 17 he was 58... I was young and stupid.... but the first time I had anal sex with a woman was in college and I was 19.

 

[Jake90]

About 10 days ago an older guy came on to me in the steam room at the sauna and started sucking me and fondling me. He was very attentive and I need the experience so I went back to his private cabin. This went on for a bit then he asked if he could fuck me. I thought why not so he got a condom and lubed me up, fingered me for a bit then I got my legs up in the air and he put his cock against my hole. Now he wasn't that big - I'd held his cock and knew he was shorter and thinner than me (maybe 5x5?) - so I wasn't scared as I have played with a cucumber bigger than that (see my gallery!). He told me to relax and I tried to remember how I pushed down to get the cucumber in. Once he was in he thrust all the way. No pain at all - just felt really good and I cried out for him to go harder and deeper. Shifting position a bit I felt his balls slapping against me. I don't know whether he came or just got tired but we agreed to stop for a rest, but we didn't hook up again as I soon had to get the last bus home.

I really enjoyed it but I wasn't that hard, probably because although he was really polite and considerate I wasn't attracted to him. Now I really want to do it with someone I find hot - maybe someone I'm in love with!

 

[lickme69]

where are the female responses??? I want to hear about normal anal not homo sex! come on ladies?

glad to oblige my story. mine actually just happened last week. I wanted to try it and asked my BF to do this and it was great!!! Hurt for a minute at first then it becomes pleasurable. Next thing I know, I was begging him to do it harder. I was a little sore the next day, but no too bad. I cannot wait to do it again!!! He had me bend over the bed with my ass up in the air and he was standing.

 

[lickme69]

here's a question. How many prefer to give than receive?