Where it happened: My bedroom
Langauge: English
Sex: Male
Rating: 10
Category: Straight
After I saw anal sex in an adult movie at age nineteen, I wanted to try anal sex. I was no longer a virgin and I wondered what it would feel like to put my penis in a woman’s anus instead of her vagina. I wondered if it really could be any different or any better for anal sex over vaginal sex. I asked my next girlfriend for anal sex and she said no to anal sex.
I did not date much for a long time. I have a hard time meeting women. I work a lot but I live a very comfortable upper middle class lifestyle. A few years had past and while visiting a friend and his wife, I started an extra marital affair with her. She felt neglected, they were struggling to make ends meet, and she was not having any sex with her husband.
Eventually, she comes to visit me and a friend of hers from high school for an extended weekend. She spent the first night at her friend’s place. The next three nights she stayed with me. She had her first orgasm from penetrative heterosexual sex with me at this time. She had forty one more orgasms in the next three days (we both counted). Keep in mind, she never had a hetrosexual orgasm before in her life.
She interviewed for a job at a newspaper near where I live. She was hired for the job and moved forty minutes from my house. We started having sex eight to ten times a week. On her thirty-second birthday, I licked her vulva for the first time. It was the first time in her life she had her vulva licked. I was more than willing to lick it, but she never asked and she said she felt embarrassed to ask for it. I love to lick vulva, particularly when a woman’s vulva is shaved which she was.
From then on, I did not wait for her to ask for oral sex from me, I just started licking her vulva whenever I felt like it. Eventually I put my finger in her anus while licking her vulva and moved my finger in and out while licking her. She had earth shattering orgasms this way.
From that point on, I knew we would eventually start having anal sex because I knew she loved me fingering her anus.
I purchased a set of butt plugs of different sizes and I used them on her. We got to the point where we could put the largest butt plug in with no problem at all. I waited until she told me she was ready to try anal sex. One Sunday afternoon, I lubed up the large butt plug, inserted it to her anus and waited a few moments until her anus was fully relaxed. Then I put some lube on my penis, took out the butt plug and inserted my penis in her anus for the first time.
It felt wonderful sliding my penis in her tight anus. We had anal sex for the next half an hour. I had sweat pouring off of me even though I was in my air conditioned house. I was nervous and unable to achieve an orgasm the first time. She had absolutely no pain and nine big orgasms.
We went out to dinner afterward and talked about our wonderful experience losing our anal virginity.
The next day, we had anal sex again. It was just as wonderful for her as the first time, but for me it was much better. I was not nervous this time and had my first orgasm from anal sex. I do not make too much noise during sex but this time I screamed her name as I ejaculated in her anus. It was just like loosing my vaginal virginity all those years ago.
Over the next month we had more anal sex. About a month later we stopped using the butt plugs because we realized we did not need to use them to get her anus ready for anal sex. As time went by we had more and more anal sex. By two months after our first anal sex, most of the sex we were having was anal sex. We would either have vaginal sex first, then have anal sex for the rest of the night or just have anal sex multiple times in one night. One incredible night, I had five amazing anal orgasms with her and she had too many too orgasms count. At one point we were having anal sex six or seven times a week.
In summary, anal sex was worth all the effort and patience. I learned the right way to have anal sex, prepared her anus for anal sex, waited until she was ready to try anal sex and I was gentle with her. Loosing her vaginal virginity was painful. Loosing her anal virginity was totally pain free. Loosing her vaginal virginity she had no orgasms. Loosing her anal virginity she had nine big orgasms. As for me, I love anal sex. It is so much more intense and pleasurable. If I have a choice, I will choose anal sex every time.
If you want to have incredibly good sex, try anal sex. If you take your time to relax the anus, use plenty of lube and are gentle with the anus, you will be rewarded with great anal sex. If you do not do these things, anal sex will hurt at least a little in the beginning before becoming incredibly good sex after she relaxes her anus. Either way, after having anal sex a few times it will be just as easy as vaginal sex and much more pleasurable. As far as I can tell there are two types of women in this world: women which love anal sex and women who have never had anal sex the right way.
As for general sexual advice, I have a few suggestions. Ladies if you want you oral sex, shave your vulva. Oral sex is much more pleasant for men when you are shaved. Men, she may be too shy to ask you but she may prefer for you to shave as well and it is only fair to her as well. Do not be too shy to ask to try different sexual activities. If there are certain things you want to try, go slowly and work up to them over time. Rushing in to more advanced sexual practices without consideration may well lead to disaster instead of enjoyment. Sex is meant for pleasure and enjoyment. You should enjoy sex to the fullest.
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