Jonathan – dating a younger man

Posted in Dating.

When I returned from my trip alone to Europe, a seasoned wiser woman, I didn’t know what I was going to do with myself. How could I top the adventures I had just experienced? Well, I still didn’t know who I was entirely or what I had to offer in a relationship but in any case, I continued to chat with Mr. Italy and France and also maintained my friendship with my chat buddy the 19-year-old younger man and American, Jon.

I did some casual dating here and there and had some adventures with all sorts of different men; A Karate instructor, a cello player, a pilot and even a lawyer. Each time I learned one new lesson from each man and I got closer to understanding a little about myself and how I was in relationships. I didn’t sleep with any of them but I did have one exclusive FWB (friends with benefits). That, lasted for a while but we mutually ended if after a few months because things got “weird” between us. We had been friends since elementary school but as soon as we got sex involved, it all went awry.

Throughout it all, I maintained my “online” friendship with Jon and turned our Internet chatting into telephone chatting. I loved listening to his Air force stories and was really intrigued about how he was still a Virgin! How could this be? I guess my fascination with his “pure as the untracked snow” image led me into flirting with him on a regular basis.

 There was also something “dirty” about him being only 19. Almost 6 years older than him, I felt naughty, I felt bad. What a dirty old pervert!!! I didn’t really know what I was getting myself into, he was “just a baby” in my eyes and it was innocent to just flirt with him on the phone but somehow…I started to develop real feelings for this “baby.”

We exchanged photos, talked on the phone and talked online almost every single day for months and months! I watched him on webcam and we spent countless nights on the phone laughing.  Finally, came the day when it was decided he would come to Canada to visit. I wasn’t sure what to expect but when he arrived there was quite a bit of “uncomfortableness” between us. We had practically had an entire relationship over the phone and the computer but now he looked so young to me, I felt guilty and like a total dirty old woman. 

 Just before Jon arrived I had spent an evening with my  ex boyfriend Ewan though. Yes Ewan, the first man I truly gave myself to and whom I thought I was still madly in love with. Once again, I “gave” myself to him and had a beautiful night of lovemaking.  It was a moment of weakness he said and left without any mention of him still loving me or us ever getting back together. I could have kicked myself for letting that happen.  Of course, this only confused me more and fucked me up beyond belief but I tried to console myself by knowing that soon this American young’un would be arriving to chase the blues away.

So here I was with this American visitor now that I had no idea what do with and a he was a Virgin no less! Feeling rejected by Ewan and confused about my emotions around him, I thought about my whirlwind romances in Europe and my “friends with benefits” relationship with my friend from elementary school. I was in absolutely NO shape to get into a relationship so naturally; I walked right into the young, strong arms of Mr. US Air Force.

Yup, I deflowered the young’un. I took his Virginity and I’m sure he loved every second of it. There was plenty of exciting sex over the next two weeks and the high of being with a new lover overtook us both. It was fun to lie around in bed with a new man. He said the most powerful things to me and made me feel in love. I felt beautiful again, I felt desired.  How exciting it was to be with a younger man…how exciting it must have been for him to be with an older woman!

The challenge came however when he announced his feelings of love for ME. We had a magnificent two weeks together while he visited but now that he had gone back to the US and I never got to see him so I didn’t have those “lovey dovey” feelings anymore and the “high” was gone. LOVE? He LOVED me? He told me how he had fallen deeply in love with me and wanted to marry me. I was shocked but at the same time happy in a weird kinda way just because I felt I had finally “won” the love of another man. Maybe I wasn’t so unlovable; maybe I could love another man again. Perhaps Jon was the key to me getting over Ewan once and for all.

We continued our long distance relationship over the phone and the Internet and the next time he visited he arrived with a ring. Not an engagement ring but rather his old school ring that he wanted me to have to remember him by until he could buy me a “proper” ring. I accepted his ring w

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