The first person I ever told about my first experience realizing that I was anally-oriented was not a girlfriend. It was a woman, an old childhood friend, not someone I ever dated. Her name is Heather, someone I'd known since elementary school. We'd been friends throughout our life and still are although we don't see much of one another anymore since I moved away a long time ago.
The experience I had was when I was about 12 and it was at the doctor's office during a checkup exam. I've already written about this story here: http://www.experienceproject.com/stories/Love-Anal/3568440. I never planned to tell her or anyone about this experience or my interest in anal sex, other than the girlfriends who ended up being interested in it, but even then it wasn't always something talked about in much detail. I always felt shameful about my anal interests so I was cautious about bringing it up with girlfriends until they seemed comfortable. But even so, I've only told 3 people in my entire life about how this one experience that got it all started. First Heather, then later a woman who I dated for about year and did all sorts of "playing doctor" with, and then much later I told my wife.
So how did I end up telling Heather who wasn't even a girlfriend about it? Basically we were in our late 20s and had one weekend where we hooked up, got naked, and did a lot of things although not intercourse. It was a time when we were both single and were having dinner one night and we both just realized, let's do it, let's have fun. We knew we weren't in love but did really like each other and found one another attractive and also really trusted each other. So she spend that weekend at my house and we pretty much spend the whole time naked and enjoying each others bodies and talking and having fun. She told me up front No Intercourse because at that point she actually wanted to save it for the guy she eventually married. She wasn't a virgin but it was her choice so fine with me.
So as far as my opening up to her as I said we trusted each other and during all the weekend intimacy and exploring and touching and etc one another, we did a lot of talking and asking questions and exploring each others sexual experiences and desires. Just out of curiosity. At one point we were talking about spanking and I told her that I'd dated a woman who liked when I spanked her on her bare ass. Heather asked me if I liked doing that and I said Yes I loved it. She asked why and I said that I loved touching that woman's bottom whether spanking or touching or kissing. Heather asked if that woman ever spanked me and I said "no, not spanking". Heather said and?????? what??? I don't recall all the words we said exactly that weekend but this is what I remember mostly.
I said something like "look you know i trust you. can I tell you something really private?" She said Of course, with a big smile on her face. I just felt so comfortable at that point in our weekend together with Heather as a friend that I wasn't ashamed to say it. So I just told her. I told her that this particular woman who I dated for a few months had been very interested in my ass, in penetrating me, and that I liked it a lot. I remember the look on Heather's face. She was quiet for a bit and then said "wow! no way! And you liked it?" I told her yes I loved it. "So she fucked you?" I said basically "well, not like with a dildo or anything but with her tongue yes a lot and then with her fingers. but yes, it was pretty much like being fucked i guess you'd say." Heather was so into what i was telling her, she kept asking questions and saying things like "god, that is so amazing, that is so hot" and I kept answering. It actually felt good, like finally I could tell someone about this and not feel weird because Heather was really interested and supportive.
So when she asked why I didn't freak out the first time that woman touched me there (on my anus that is) I told her that it was something I had wanted her to do and actually i asked her to do it. Heather said something like "how did you know you liked it?" Instead of talking about the few previous experiences I'd had with other women, I decided to tell her what I'd never told anyone at that point. What happened at the doctor's office that day when i was younger, middle school, and how it made me feel. And I said "look, this is going to sound weird but I want to tell you what happened to me once at the doctors office." I went on to tell her the story, about the moments when the doctor unexpectedly pulled my underwear down and examined and touched my penis and testicles and then turned me over and spread my bottom wide open and examined my anus. She listened just staring with bug eyes as I talked. When I finished she said "that is so so hot! I would love to see your face walking out of the doctors office that day! oh my god!"
I felt like I was blushing when I finished telling Heather this. I told her I felt embarrassed right then and there and that I'd never told anyone about it not even my previous girlfriends. She actually said "thanks for trusting me" which made me feel good a bit less embarrassed. Of course it was already going through my head that it would be an amazing experience to relive it with Heather playing the doctor. But just at that moment I didn't bring it up. Even after being this open and intimate so far I wasn't confident about asking Heather to play doctor like that. And she didn't bring it up either so part of me thought if she doesn't bring it up then I'm not going to. But as we kept touching and kissing and sucking and licking one another that afternoon Heather paid more attention to my ass, just stroking my cheeks and gently touching along the crack but not exploring in between, but that gave me enough confidence to ask her finally.
I sat up and looked at her and asked her if she'd be willing to play doctor and do to me what my doctor did to me many years before. She immediately said yes but i kept talking probably because I was nervous and said 'Look I know maybe you don't want to look at me like that, I mean back there", she just interrupted me and put her hand on me and said 'Don't worry about it, I want to do it!." Of course I was so excited at this point but still nervous at what was about to happen. I quickly left and took a shower wanting to be completely clean.
When I came back I had a pair of underwear on and she patted the bed "up on the exam table please". So I lay down on my back with my stomach in knots. And of course I was already pretty hard which was not the same as when I was 12, I didn't get an erection then I don't think. It didn't really become a full Playing Doctor situation meaning that we didn't really talk about it before and she didn't actually talk like a doctor during it but all that was fine. I didn't care. She was smiling the whole time and I'm sure I was too. I asked her to turn on the bedside reading lamp, she said Of course, just like at the doctors!. She pulled my underwear down to about my thighs and really gently and thoroughly touched and "examined" my penis and my balls. It's not like she hadn't already seen or touched me there, of course she had. But this time she was taking her time and not doing it as something sexual (even though I was totally aroused!) but more just enjoying looking at me in this intimate way. She took way longer than the doctor did and I loved it, especially the way she brought her face in so closely to look and use her fingers to explore every part of me and feel the textures and how soft and hard the different areas are. Amazing watching her do it. Of course the feelings I had were incredible and I felt hot all over.
Then with a smile she pulled up my underwear and said "Very good Richard, now I will need you to roll over to continue the examination", very professional. I couldn't believe this was about to happen. Not just to relive this experience that had stayed with me for so many years but the fact also that I was going to have my good friend look at this completely private part of my body. That she actually wanted to, or at least she said so. I'd never imagined in my life that this would happen with her just like anybody wouldn't think that a good friend would see you in this off-limits way. So I turned over feeling kinda dizzy with the anticipation and excitement. "OK" she said as she pulled the underwear down again and I absolutely felt my face go red as the air touched my exposed bottom. "I'll need to take a look here now" she said with her palms on my cheeks and then pushed her hands apart and WOW, I felt like a kind of point of no return. Totally exposed, oh my god. She didn't say or do anything, but she kept adjusting her hands a bit. "Oh it's so pink", I will never forget those exact words she said in a kind of whisper. She seemed to adjust her hands and then used her fingertips to keep my bottom spread open. I wish that I had a video of the whole thing, just to see what it looked like to watch her examine me and also to see the expressions on her face. I thought maybe she'd only take a quick look and then it would be over and we'd get back to what we'd been doing all weekend. But she actually was taking her time. She asked then "so did your doctor actually touch you there?" I told her No that he just looked. She asked 'Can I touch you there? I'll be really gentle." Obviously I said YES! It's funny now but she never said anything but 'there', she wouldn't say 'asshole' or 'anus' or some other word, like she was embarrassed even though she was right there looking at it and about to touch it!
Feeling her fingertip touch my anus was like a little electric shock. I know I tensed up because she said "Ooo, it tightened." I told her it's ok, it feels good, go ahead. She just used her one finger to touch all around the area, above and below my anus and on the anus itself. For anyone who has had their anus touched and likes it, you know what I mean. It's a feeling like no other. And of course it makes your head spin because it's such an intimate act. Especially like this where you're basically at the mercy of someone, submissive in a way. I felt her use two fingers to spread right in the middle and she said "it's a really dark pink inside, it's really smooth the skin in there." Looking back now its hard to believe that I didn't ask her to put her finger inside me, that I didn't ask for a "rectal exam". I don't know if I was just too sort of dizzy from it all or felt that it would be too much to ask, like, how far should I push this whole thing. Now I think WTF why didn't I? But anyway I didn't. After that comment she make she stopped what she was doing and kinda caressed my cheeks and said something like 'you have such a nice ass you know that?" I took that to mean that the exam was over and I turned back over and looked at her. I'm not sure what I said.
We didn't talk about it any more after that. The weekend continued as it did before and actually she never touched me back there again and that was OK with me because I was still half freaked out half embarrassed half excited by the whole "doctor exam". I mean obviously I pretty much have been for the rest of my life. I would love to sit down with her and talk about it one day, but I suppose that will never happen. What if she reads it here and recognizes us?
Would love to hear of other's experiences in discussing their first experience with someone.