Oh! I have just been proven so wrong and nearly missed an experience that I am so pleased I didn’t.
Let’s call him “the boy.” I was living in Orange County, California at the time. The boy and I have been in contact a few times over the months but we never managed to meet due to scheduling and I didn’t think too much more about it. Until tonight.
I got a call and he said “I am standing in town, let’s meet” I remembered he was a bit younger than me and his cockiness and very endearing arrogance told me I was right. He was 25 years young. I wasn’t sure if this was an ideal match but after my previous escort client being pretty uninspiring I decided to go for it and see. I was really desperate to orgasm and loose myself in the moment and feel some connection, the day had proved taxing and one where I was very certainly “the escort” and not seen as me so I had absolutely nothing to loose.
The boy rang back and asked me if I was going to text my address or not, I was still thinking about it and unsure about the age gap. For some reason I have made a rule never to have sex with a man younger than me. A few have slipped through the net so to speak and I have never had a bad experience so I am guessing this is more to do with me than anything else. Anyway, too late as I decided to throw caution to my silly rules and texted him my address and a message saying “you better be good in bed” he relied “I am rubbish” not what I wanted to hear but given his charm I was in little doubt this was another of his boyish jokes — I was 15 minutes away to him arriving from Anaheim and wondering if wine was a good idea or not.
Somehow, he managed to get into the building without even calling so now he was outside my door and when I answered he really did look young, with a cap, a cheeky smile and was certainly not shy. We sat for a few minutes chatting and sparked off each other instantly, I liked him. He was fresh, cheeky and quite frankly a breath of fresh air after the afternoon so we shared a glass of wine (only one as he was driving, must have just past his driving test!) and then all hell broke loose.
I removed his cap and ruffled his hair, he said he was worried he was going bald? Oh please! For the first times since arriving he looked sheepish and lost so I asked him to kiss me and off we went, he picked up pace and told me to “lift up” as he removed my black dress in one and then with me standing in between his straddled legs he unclasped my bra with one hand. “I am an expert at that” he said with a sly grin. Oh the total cheek, I was loving it! An escort in Orange County like me wasn’t use to such playfulness.
He turned me around and both of us looked into my mirror and the sight of his chest and arms above my ass was pretty nice, he licked and caressed me and I sucked his ever growing cock until it was hard and impressive in stature. He wasn’t backwards at using his fingers with the skill of a man twice his age as he knew exactly where to find my G spot and make me nearly loose my mind.
We screwed hard and soft well, (actually mainly hard) and after various positions, all of which he pushed me in and out off he came on top of me and his ego and cockiness disappeared and his boyish charm was there once again and it was lovely. I so enjoy a man that enjoys women. For all you women out there, I highly recommend this Your Tango article.
So, all my reservations of the boy were wrong. He was a wonderful mix of beauty, arrogance, charm and cheek all on the correct levels without being overwhelming. I had a client who was 21 once and he picked me a flower on the way and was adorable and this 25 year old shared the fun and youthfulness we can sometimes forget is there still so I have decided to bend my rules and be open to suggestion. To add to it, he put his hand in his pocket and gave me $20 at the end and said “have a cocktail on me.” It was funny and also very sweet and slightly condescending, he knew it, I knew it and we both parted smiling from ear to ear.