The first time Autumn inquired if I would like a prostate massage, I replied that I had never had one, and that was entirely true, but I realized just this past week that I had experienced anal penetration before... 24 years ago. So this might sound like a Penthouse letter of old, and I apologize if it does, but I'm not sure if I've ever told anyone, and Autumn's site seems like a perfect place to recount my first anal exploration.
I was single, in my early 40's, and living in Asia. I had just returned from a quick trip to Australia for a friend's wedding. It was new year's eve, and on the return flight the aircraft would be crossing 3 time zones, and new year's eve could be celebrated three times. It also meant most of the passengers were asleep during that time, but because I was still under jet lag from the inbound flight a few days before, I was wide awake. Hannan, was one of the international flight attendants, a smile that lit up the dreariest economy class section, and dark brown eyes that were as bright as her smile. After asking my beverage choice, she hesitated; "Have we met before? I feel like I know you?" "No, I'm afraid not, but I wish that we had." Her slight blush, wide smile needed no other words, but what made the connection more intense was the fact that she lingered, a moment longer, and then stopped in the aisle and turned to me again. "Sparkling water, right?" I nodded, and held her glaze for another moment.
A few hours later, while most passengers were asleep, I was reading. Probably a Wilbur Smith novel, and because I was alone in the aisle row, I was startled by her as she sat down beside me. I had never had a flight attendant sit down beside me. We chatted easily about family, home and travel, favourite places, etc. After about 20 minutes she slid her hand over to cover mine (which I wasn't expecting from a woman raised in a Muslim family). "It's new year's eve, and we have champagne opened in the back galley if you'd like to join us." I stayed in the back galley for about 2 hours enjoying the company of all the attendants and conversation but left to my seat once the fasten seatbelt and call for landing came. I didn't really have a chance to talk to Hannan again until the passengers were departing. I came into the exit hall and waited long after the plane was empty until the flight crew came down the hall. It was quite obvious who I was waiting for, and the head attendant tilted her head to Hannan and motioned her over to me. I suspected there had been some girl-talk about me previously. We walked together, not too close but close enough to exchange small notes with a phone number on it, and email address. We laughed, as we both had taken the time to write things out and prepared a way to stay in touch. I would meet her at her hotel the next day and go to the Botanical Gardens for a stroll. All went to plan, we had a lovely afternoon stroll through the park, got to know each other more, and were headed for a nice dinner. She turned to me with a serious look, gave me a quick soft kiss on the cheek and whispered, "I don't like eating anything heavy before sex, can we just go back to the hotel?" I thought I was taking things slowly and quite willing to let things unfold that way, but she obviously had other intentions. To the hotel. Inside the room, passionate kisses, a slow removal of clothes and rubbing bodies and body parts until "going horizontal" was the next step. My preference is always pleasing a woman orally first, always. I told her this. "Yesss... please, as long as I can do the same to you." "Of course." And we did, and it was very natural, beautiful, slow and fulfilling. While we were both in a lovely state of satisfaction she began to tell me how she always felt like she could have been a boy. She played soccer with her brothers, wrestled with them growing up, sometimes went out to play in the neighbourhood or to events dressed like a boy so she could have a bit more freedom. And as much as she enjoyed sex as a woman, especially an orally induced orgasm (the only way she came she told me) she really wanted to fuck a man. "Oh, so how would that work? Now remember these are the days before "pegging" or "strap ons" were talked about (at least in my circles) or evident in any pornography that I might happen to stumble upon. In some parts of Islamic Asia at that time a dildo might even be considered illegal or confiscated at an airport. "I've never done this, but I've imagined it often. Lie on your stomach and raise your ass up. I'll kneel behind you, put my hand against my pussy, stick out a finger and fuck you with it until I get off." I was intrigued, felt a bit dominated at her very direct description, but also was thoroughly excited, and had become hard again. She looked down at my erection and smiled and she gently stroked her fingers along it. "I think you'll enjoy it." I was still nervous about the cleanliness of it all. "It might not be umm, very clean." She laughed. "That's why they invented soap and water." She picked up a bottle of suntan oil and gave a "so?" look at me. I just turned over onto my stomach and she put her lips next to my ear. "Thank you Habibi (Darling, in Arabic)." And she did exactly as he had described. I felt her thrusting inside, and it wasn't unpleasant, but more exciting for me were her movements and breathing and the pulse of her finger. She would pause when her finger had reached it's limit, and her hand was still moving side to side and rubbing against her pussy and clit. She came loudly within two or three minutes and collapsed on top of me. I let my legs slide back, my stomach back on the bed while her breathing started to calm, but her finger was still inside me. She rolled me over to my side, sat up a bit and put her other hand onto my cock. A little more oil and stroking and I also came quickly and hard. I don't remember it as an intentional prostate massage, I don't think I even knew what that was at the time, but it was very pleasurable, and never to be repeated until I met Autumn. And so thankful I did.
Post Script - Hannan's flight schedule changed to the UK and North America, and although we emailed from time to time, unfortunately I never saw her again.
Σχόλια