How I Lost My Virginity Twice in the Same Summer

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Oca 13, 2023 // By:analsex // No Comment

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To understand this story I first must explain my high school years.  I was a guy who excelled in sports and was well-liked and known throughout my high school as well as in the community.    My biggest downfall was that I was very shy.  I could function within a group of friends who were just hanging out or watching sports, but when it came to talking with a female or giving them a compliment I just froze and would become quiet. This really hurt my social life and it was a source of great frustration for me.  I would see others who would be with a different woman all the time and wondered what was wrong with me.  I would also hear the other guys talking about who they fucked or got a blow job from and would wonder why not me.  I would never tell them that I was still a virgin but then again I could not understand why I couldn’t get laid.  It is not as if I was unattractive.  I was six foot four and a solid frame from working out on a regular basis.  I had black hair and because of my Italian descent I had an olive complexion.The summer I graduated and before going off to college I wanted to enjoy that summer but knew I needed money to do that.  I decided I was going to canvas the neighborhood and surrounding areas informing everyone that I was going to be doing yard work for the summer.  I would cut their lawns, trim bushes, weed, etc.I no sooner put my flyers out and my phone started to ring.  Before I knew it I had more customers than I expected within a six-block radius of my house.  This was great I could work on my schedule as long as I got the work done and will be making some good money, besides it got my parents off my back now that I was going to do something this summer.  Spring came and it was a bit hectic at first until school was out but once school got out of my way it was great being able to schedule as I wanted.  A few weeks into my business I received a call from Mrs. Martin who lived three blocks away.  Mrs. Martin and her husband Barry were the only black neighbors that I knew of for miles and miles.  Mrs. Martin was an extremely beautiful woman.  She had long black hair, beautiful brown eyes, long legs that flowed up into an amazing tight ass.  She had a gorgeous set of 38DD breasts.Her husband Barry was a built man who use to play college football at a large university in the east.  Once they were around I use to enjoy talking with him and hearing about the games he played in and what teams he came up against.  As I was saying Mrs. Martin phoned me in a panic.  She told me that her normal lawn service just advised her that they were going out of business and would have to get someone else to do their lawn.  She told me the McGregor’s told her that I was doing lawn service this year and asked if I could take them on as customers.I told Mrs. Martin that I had a full slate of customers.  I could hear the disappointment in her voice once I told her that.  I then told her that I hate to turn anyone away so if she could be patient with me until I get my schedule set in stone I would be able to get her into a regular rotation of customers.  She was so happy and istanbul travesti you could just hear her stress level go down.  I have to admit I really felt good knowing I helped her out even though it was in such a small way.  They really are very nice people and have always been extremely friendly to me.As the weeks went on I set my schedule and arranged for days to make-ups for the rainy days.  Things were running smoothly and I have to admit I was making great money and was not really working all that hard.  Most people were at work and not at home when I was there so I could do what I had to do at my own pace.That is except for Mrs. Martin.  She had a job where she mainly worked from her home so she was there all the time.  I cannot say I was upset about that since she was very nice.  She always brought me out a drink and would talk with me about my plans and what I’d been up to.  She would also tell me to jump in the pool and cool off if I liked to.  That year we had a stretch in May where we were having an extremely hot heatwave.  The temperatures were ranging from the mid to upper nineties. I went to the Martin’s that Wednesday to cut their lawn.  I took my shirt off while I was cutting because it was soaked with sweat.  As I finished and was putting the mower into my truck Mrs. Martin yelled out of the window and told me to come in for a drink.  I couldn’t see where she was but yelled back, “Thank you, I’ll be right in.”I went to the door and didn’t want to just walk in so I knocked, “Come on in Mrs. Martin yelled, I’m in the kitchen.”I opened the door and walked to the kitchen, as I entered I stopped dead in my tracks.  There was Mrs. Martin standing there in a very skimpy white bikini.  She looked breathtaking, the white bikini against her black skin was so sexy I could feel my cock twinge from the sight.She looked up and smiled at me as she placed a glass of ice tea at the counter.  “You really did work up a sweat out in that heat today, it is so hot I decided to spend the day poolside since it is too hot to do most anything else.”“Yes it is a hot one, but a little hard work and a good sweat will never hurt anyone,” I told her. She gave me a grin as she replied, Yes but there are better ways to get a good work out that are much more fun.” As she continued to move around the kitchen doing things as we talked my eyes wandered as I could not take my eyes off her amazingly sexy body.  Her tits were almost popping out of her bikini top, and her tight ass looked incredible.  I couldn’t take my eyes off of her.I finished my drink, and thanked her telling her how refreshing it was.  She picked up my glass and turned to put it in the sink.  As she turned I had to readjust my hard-on so it was not too obvious when I got up.“Are you sure you don’t want another one?”“No, thank you, I do have to get going. I have one more lawn to mow today.”“Well you more than welcome to skip that lawn and join me poolside.  The company will be much appreciated.”“It is a tempting offer, but I do have to get it done before they come home today.”“Well if you like feel istanbul travesti free to come back after your done just come back to the pool. I will be there.”I excused myself and left, but I did not go to my next job I actually went home and had to jerk off thinking of that beautiful body Mrs. Martin had.  I thought about how my mouth was on her tits sucking those beauties before I crawled on top of her and rammed my hard dick into her black cunt.  It didn’t take long before I erupted to a wild orgasm where I exploded with a huge load all over me.The rest of the week every private moment I had, my hands were on my cock stroking it as I thought of Mrs. Martin in that bikini.  A week went by and I was going back to the Martin’s to mow again.  This week I only scheduled them for that day.  My thought was if Mrs. Martin invited me to stay and swim today I was going to do it.With it still being very hot I got my mower out and took off my shirt.  There was no sign of anyone around as I thought to myself, “Looks like I won’t see her in that bikini today, just my luck I planned for it for nothing.”As I was mowing Mrs. Martin pulled into the driveway.  I tried not to be so obvious but I watched as she got out of her car to go into the house.  Mrs. Martin had on a short blue floral dress with matching blue heels.  She looked gorgeous as she made her way into the house.  I was just so thrilled that I got a glimpse of Mrs. Martin today.  It had become the highlight of my week to see her.I finished the front lawn and moved to the back of the house to do the back yard.  I made a few swipes with the mower and some movement in an upstairs window caught my attention.  As I looked up I could see Mrs. Martin standing naked in front of a full-length mirror in her bedroom.  It was a way I could get a perfect view of her naked body.  My cock grew once again because of her beauty.  I knew I was going home to jerk off as soon as I was done.Once again as I was loading up my mower, Mrs. Martin yelled out telling me to come in for a drink.  Going to the house this time I just walked in and moved to the kitchen.  Mrs. Martin was pouring the ice teas as I walked in.  She was in another bikini but this time it was a sexy yellow bikini that again barely covered her.  “Have a seat, sweetie,” she told me.  Just hearing her call me sweetie almost made me cream in my pants.  We sat and made some small talk as we drank the tea.  My eyes were locked on her tits as they were once again popping out of the top.  As we continued to make some small talk her question became more personal than they have been before asking me about my dating life and who I was seeing.  She was shocked to hear I was not seeing anyone. I finished my drink and again thank her for it.  Thinking to myself that it doesn’t look like I would get an invitation to swim today.  She stood and took my glass to put in the sink and there were those golden words, “My invitation still stands, would you like to join me for a swim today?””Today I have nothing else to do and it would be so refreshing to swim today with you.  istanbul travesti I do have to go home because I don’t have a suit with me.”Mrs. Martin as serious as could be looked me straight in the eye and told me, “You don’t need a suit if you do not want to.”  She saw me turn beat red as she told me that.  “Don’t be embarrassed,” she said, “you have seen me naked and I am not ashamed.”I was shocked that she knew I was looking at her.  I stumbled and stuttered telling her I was sorry for looking. She reached over touching my hand.  “Don’t be sorry sweetie, it is natural to want to look at other naked bodies.”’If your uncomfortable I would join you, I love to be naked in my pool.”As she was saying that I watched as she took her bikini off and stood in front of me naked.I couldn’t believe what I was seeing, her beautiful chocolate body standing in front of me, her huge tits with big dark nipples and her smooth pussy just an arm’s length away from me.  She walked around the counter to me and stood next to me.“Do you need some help,” she asked me as she reached for the waistband of my soccer shorts and pulled them down.  I didn’t know what to do, I was paralyzed.  She lowered my shorts lower exposing my rock hard eight-inch thick cock.  She looked up at me smiling, “Oh you need to show this baby off.” Taking hold of it as she gently stroked it.  This was the first time anyone but myself ever touched my cock and it was incredible.”Maybe we should enjoy ourselves before we take that swim.”  She knelt before me and no sooner had she finished her statement that she wrapped her lips around my cock and slowly took it deep down her throat.  I closed my eyes and remember thinking to myself I can’t believe how amazing this feels.Mrs.Martin worked her mouth up and down on my dick as she caressed my balls as well. I was so worked up I lost all track of what was going on around me, I just focused on the feeling I was receiving.  Before I knew it I felt my body quivered and an indescribable feeling came from my cock as stream after stream of cum shoot into Mrs. Martin’s mouth.  She wrapped tighter around my cock and sucked and swallowed every drop of cum from deep within me.Mrs. Martin stood up and pulled me into her burying my face into her ample breast.  “Have any of your girlfriends sucked your cock like that baby,” she asked me.I mumbled out that no one has ever sucked my cock before.  I felt her body tense up and pulled away from me.  “Are you telling me you have never been with another woman sexually before?”“No, Never.”She smiled, “Oh I like the idea of taking your virginity and teaching you the needs of a woman.”Come with me baby, as she took hold of my hand and guided me upstairs to her bedroom guiding me onto the bed as she lay next to me.  I had so many thoughts about this wondering if it was okay, if it was something I should be doing, wondering about her husband, but I kept going back to how amazing that blow job was and I didn’t fucking care about any of it. I just wanted more.My hands moved to Mrs. Martin’s breast as I caressed them.  Amazed at how soft they felt.  My mouth moved to them as I took one of her nipples into my mouth sucking on it.  Thinking to myself I must be doing something right because  I could feel her nipple grow in my mouth.  Her hands caressing up and down my body as I continued sucking her tit, it felt so good having someone else touch me.

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