Unusual Path to Pegging

I received this story from a reader who wishes to remain anonymous, but desired to share his story about how he discovered pegging. It is a very unusual story. For most men there is a lot fear of being seen as gay connected with pegging. Men who love pegging seem to need to adamantly declare how straight they are as a reassurance to their partners and perhaps themselves. The gay connotation is a strong one. I really admire how this man embraced and explored his yearnings in an interesting way even when he didn't fully understand them...with surprising results.

Dear Ruby,

Thank you for your website and I would tell you my experience in the act of pegging.

I've always have been a very sensitive man and sometimes I've wondered myself if I might be gay. When people meet me for the first time and I tell them my age nobody believes me and think I'm at least 10 years younger. I thought this was a sign of being gay or at least bi as everybody who was straight was getting older by the year.

At a certain age I was unhappy with my sex-life and started experimenting with guys of my age and became a so called bi-sexual man or b-boy. I had one boyfriend on the side but I couldn't love him like I loved my girlfriend. I was just not into what he wanted from me. He wanted to kiss me and whenever it happened I disliked him instantly and would run away for a few weeks or months. He wanted me to do fellatio on him which I really disliked and I ran away again to the point I broke up my relationship with him.

I have nothing against gay people and even a lot of my friends are gay but there was always something missing for me in the bi and gay scene and I couldn't bring up what it was.

My girlfriend at that time was very patient with me and didn't mind sharing me with bi-boys. However at a certain age/time she became more and more jealous and in the end we broke up with each other over her jealousy. My heart was broken because of it. She was the love of my life and I had the feeling I blew it big time.

A year went by and I worked for an international company in an office abroad. So I was not around anymore and we lost what precious little contact we had after the initial breakup. Every day I was thinking about her and even dreamed of her every night but I couldn't lie to myself and continue our relationship without the whatever feeling I had for bi-boys.

After a year I did receive an email from her if it was possible to get in contact with her as she missed me horribly. I send an email back to her that I still felt the same for her and missed her very much as well. We started chatting at that time and we decided that we would meet to see if there was still something there to pursue. That was last year.

So I went back to my hometown and met her in a restaurant to have a dinner. When we met each other the feeling was all back again and we didn't make it to dinner and went straight to her home.

We started to make out and she told me that she might have a nice surprise for me and she went to the bathroom and came back with lube and a strap-on. At first I was like: "What the ....!?" and was kind of flabbergasted. She took my virginity that night and looking her in the eyes while penetrating me was the most intimate thing I'd ever felt in my life. When she penetrated me I felt a love and passion I'd never felt before and I instantly knew what I'd been missing in my sex-life for the first time. The passion I kissed her with that time was overwhelming to her and she and I went down on each other for at least 4 times that night.

You should know that I've never had the urge to let a guy penetrate me as I didn't even liked to kiss or blow them. I just didn't want to and when my girl went down on me I knew why. The look of your girlfriend while penetrating you, the opening of your own body, smelling hers clearly as you've never smelled her before, the passionate kissing was the utmost feeling I could ever ... ever get out of sex in my whole life. I loved every part of her and the finish was staggering.

We are very happy together and we recently bought a strapless one with a little buzzer for her pleasure. This was the missing link in our relationship and we continue to do this at least every week. We do it out of love for each other and cannot relate to the dominating versions we see online ... we actually loathe that way of doing it.

I just wanted to tell you my story and maybe other men/women or couples could get some inspiration out of it!