Using my assets

I feeling admit I am awkward type guy, no good at sports and short at 5 foot 1 inch and skinny. I've only one thing my favor a trust fund, being the runt and youngest of 7. It's all I have going for me while university. I'm Arthur 23 not the idea of a son my father George had when my mother Gloria was pregnant with me. But at least they try to make my life good. I lived off campus because I would get picked on living on the campus. My family bought a cottage in a quiet area not to far from the campus. Mostly old couples living around me, the only single beside myself is Ashley 58 widow who lives right next door to me. She a quiet lady who reminds me of the old librarian in old movies, but not strict like they are in the movies. Quiet and nice to speak too and is the only neighbor I have really talked too. I'm studying economics and I also dabble on the share market as well and do okay, I don't take risks. But coming from a family who made their money in stocks and bonds, I hear things and sometime I might take a chance. I limit myself to two thousand dollars investing maximum in the market on these chances, so if the share does well I do okay, if as has happened I only lose a little. Last year I was doing a project and didn't need to go to campus for a few days. I was home and saw a couple of people talking to Ashley and she looked upset. After they had gone I went and seen her, she told me it was the bank. They had loaned her late husband Donald $5000 which she didn't know about and he died of the virus in 2020 and she hadn't paid any of the payments as she didn't know about the loan. She had checked his papers after they had left and found the loan agreement. So she had to pay it back plus interest and penalties now around $10000. Money she would have to find quickly or lose her house if taken to court. I had more than enough money pay it for her, but thought the penalties were a bit high. But the bank wouldn't take notice of me. So I called my oldest brother Alexander who worked in banking and in the corporation headquarters of the bank involved. He knew Ashley having met her once or twice when visiting with my mother. He couldn't get the loan canceled or the interest, but got the penalties waved. Ashley was grateful and would still have to sell treasured things to raise the now $6500. I told her I wasn't in any hurry. She did invite me over for dinner as a thankyou. After the Friday evening dinner, we sat talking and as usually happens I got asked if I had a girlfriend yet. No I responded and added not likely as I'm not the ideal catch am I. She smiled and realized I wanted to get off the subject and so we talked and my studies until I went home. The net afternoon around 2 she asked me to come over to see her. I was up to date with what I was doing so I went over. Ashley said sorry for bringing up the subject of a girlfriend. I said no worries it's the way thing are, she no you can change things if you try she responded. She went on to say all I needed was confidence with women and my relationship with women will improve. How can I do that I enquired as they don't see me at all at the present. Then she looked at me and said you get trained on being around women and how to treat them and love them properly. Not thinking I had any chance either of me getting to know or even love them, I said my magic wand is broken and can't be fixed. Mine isn't she responded adding I will help teacher you everything you need to know. I looked at her and enquired what about the love part, I will teacher you that as well she added. You mean you would have sex with me or am I jumping to far I asked. No I will teach you to fuck and please a woman and we can call it interest on your loan to me she said. I was shocked by her offer, but as is usually the case my cock decided it was great idea and went hard as a rock. She said I see your aroused by my offer how about you show what you know in my bedroom now. I was still thinking it thru so she took my hand and led me to her bed. I had my first fuck and a very awkward fuck at that. But had me do again and again, each time telling what to do and after the third time we fucked she said I was much better. She told me to stay overnight and she would teach other things and we could try them out as well. Every week she made a payment off the loan to me and gave me interest as well, I also gave her a birthday present a hair salon visit. She wasn't going until the debt was paid she said and she rewarded me that night very well in bed. I also notice my interaction with girls at the university were better, but still not enough for one of them to agree to date me. But I was more confidence around them and it was helping. Ashley went to visit her sick sister for a few days, I was at a lost and so hired a hooker off the internet. Something I would've dared do before. But I was when Ashley got back and we got straight into training. Last week I asked a girl named Alice 22 out on a date she like me quiet and reserved and she accepted. We've only had one date so far and that's one more than I've had before. Till I get a girlfriend draining my balls, Ashley will do it for me she says.