Fall semester of my second year I moved into an apartment and three weeks later my roommate up and left school to join the marines. He gave me two months share of his rent but I knew I would never make it financially on my own. I worked part time at a small coffee shop and the owner was a bear of a man. Some nights when I closed we would get naked and fuck. I told him my situation and needed more hours. He tried to give me 5 additional hours each week.
Each morning I would open for the business rush. I began noticing an older gentleman, salt and pepper hair, well dressed and very handsome. We chatted, he was fit…tailored suits and very engaging with a smile and morning greeting. About a week later he handed me his business card, nice stock print….Alexander Gillespie, III. Esquire . Private number. He spoke with a strong, confident voice….call me son, we need to discuss a proposal. Hell….the rest of my shift I was zoned out. At one o’clock I texted the number. A couple of minutes later…my phone rings. He sternly said…you were told to call…not to text. He abruptly hung up. Fuck, ….i gathered myself and stepped outside to empty the trash and called. He immediately answered…sweet and wisely said….see, much better….you can follow directions. We talked. He invited me to dinner…I was curious and wanted to know more. I met him across town at an Italian restaurant that I later discovered his brother owned. Alexander wore a linen shirt and dark black jeans. He looked very distinguished. He ordered drinks, we discussed school, my schedule at the coffee shop and my practice session for the rowing club. As dinner progressed he told me I was very impressed with me. He said I was extremely handsome and wanted to offer a plan. He handed me a folded note…. One weekend at my lake house. Phenomenal man sex. 5k. No strings attached. I looked up and was surprised. He winked and said….seriously, I think you are extremely sexy, the perfect body shape and having observed me at the coffee shop, he must pursue me. I’ve enjoyed man sex since high school. My swim coach at the country club rimmed my ass so well. I have always been attracted to older men. Yes, I did need the money. My boss and told him my roommate moved out. So…it was a transaction…nothing more. He stated as the lead attorney for his law firm….he would require a contractual agreement to not disclose this transaction. That evening he handed me an envelope with 2k in it. He said come with me to my city condo for a blow job now. If you don’t like our connection this evening…we can walk away and go our separate ways. Hell….absolutely yes..was my response. He called his driver…we left the restaurant and as soon as we got in his car …he leaned over and kissed me. Damn…the wine taste from dinner was delicious. His condo was in a high rise in midtown. Once we stepped out of the elevator…he took my hand and lead me to the bedroom. No small talk….he used a remote and the blinds raised to the city lights were amazing. He told me to strip… hands up on the glass window and present my ass to him. He kissed my pink hole. Tongue fucked me… my precum dripping on the glass. He carried me to bed and in one swift motion….swallowed my 7.5 uncut cock. He fingered my ass as he sucked my cock. I was in another world. He was a skilled cock sucker. He was very attentive to my low hanging balls; rolling them in his warm mouth. I couldn’t resist….i shot a massive load down his throat. He kissed me and we both ate my load. He returned to bed with a warm wash cloth and cleaned me up. He kissed me….and in a low voice….ill give you an additional 5k tonight if you will sit on my cock and I fuck your ass. Hell…he had eaten me so well and the rim job left me wanting. After he fucked me he sucked me off again. We held each other in his massive bed. He handed me an envelope. We dressed and he called for his driver. I figured he would send me on my way. He rode with me back to the restaurant and walked me to my Jeep. Before I left….he walked to the restaurant and returned with a brown bag. He said his brother prepared me a couple of meals for the week.
The next morning at the coffee shop he presented himself calm and collected. He winked and said …. Call me at 12:45. I told him I had class. He said….call me. I had about 15 minutes left in my lab. I excuse myself and went to the men’s room. He was eager to hear from me. We made plans for that evening. His doorman anticipated my arrival. In his condo he had a meal ready. Legal papers. A contract in some ways. Asking for 2 nights each week. One day a weekend ….preferably Sunday since I had rowing club on Saturday. A 5k bonus for a weekend once a month. Total compensation would range from 5,000.to 8,000. I told him last night was amazing…why pay for sex. He corrected me and said I’m paying for your attention and exclusive access. I signed the contract…..he fucked me on his white leather sofa. I kissed him and ate his ass. He told me…fuck me until you are ready to cum. He instructed me to shoot my load on his feet. Of course I obliged…after I shot my load on his feet. He requested I lick his toes clean. A first for me.
By Thanksgiving our arrangement was very beneficial for both of us. It was completely at ease and I must admit I was developing feelings. One day at the coffee shop a gentleman entered the business and asked for my Jeep keys. He told me Mr. Gillespie had sent him; of course I completely agreed. An hour later Alexander called. Told me to meet him in the parking lot. He handed me my keys. Oil changed, new tires, and a credit card on the dash for monthly expenses. In passing last week I told him when I go home for Christmas break I would have to purchase new tires before winter.
This man was so sweet and happy when he made me happy. The sex was amazing. One weekend I could get away we flew to Seattle for two days. I met his sister and her family. I was falling in love with him. One night at dinner he gave me a key. He told me to break my lease and move in with him. I told him…thanks… but I liked our relationship the way it is. I had to concentrate on school, rowing club and my job.
That night he fucked me in his car in the parking garage. He told me he couldn’t wait to get my ass. He was so good as a lover. Not sure what happens next…but I love this amazing man and crave his fat cock whenever I can get it.
