Fourth Time is a Charm Ch. 01 by Bigguy7979,Bigguy7979 I was done with love, I had just had my heart broke by the 3rd woman in 3 years. I tried to do everything right. I paid for dates, I waited a few dates for the first kiss, I gave them attention and showered them with gifts. I even gave space and comfort when the situation called for it.
I dated Amber at the tail end of college, she was very good looking, she had an hour glass figure but a skinny waist with a nice set of tits. She was real wife material if I had ever saw it. I loved touching her hips as we kissed and she returned all the affection.
Then one day about 4 months in, and about two weeks after we first made love, out of the blue, she up and left me. I thought it was something to do with my performance in bed initially. I had nothing to be ashamed of a 8 inch cock, I made her cum at least 3 times each time we made love, and it was a few hour each time. I knew I had to put in my best for her, a woman as gorgeous as her was not something to put partial effort into. Stamina was not an issue, I had a high sex drive and cold stay hard for hours, even after I came. I worked out regularly to be appealing to her, it was something I took pride in. I thought to my self when she left that unless she was faking all of the orgasms I gave her she might have been screwed in the head, she genuinely looked like she enjoyed every night of passion.
After the breakup I tired to get her back, she flat-out said we were not compatible. She broke all contact with me. I did see that my sister and her remained friends, at least on social media. My sister Ashlee lived back home on the other coast anyways so they were not close friends, but they had been known to communicate online when we dated. They had only met twice and I would not be surprised if Amber forgot she was friends online, Ashlee never posts, may not ever be on that site anymore then in the beginning of our relationship. Ashlee had got a new internship and was really into her new job at that time.
After a few months that was all in the past anyways, I met another girl, Ann. Ann was another woman who was out of my league just like Amber. She was a pretty southern bell. Her tits were not as big, B cup at best. She had a skinny little ass thou. She moved to the area for an intern job. Once I saw her I knew I needed to at least try and shoot my shot. Luckily with her being from the south and me being from Virginia we clicked. I treated her the same way, although we did start having sex earlier on in the relationship.
She was great in the sack, and I was a generous lover, I ate her out pretty much every time to at least 2 orgasms before I gave her another with my cock in her sweet tight bald pussy. Her clean shaved pussy was the first hairless woman I had been with down there. I Enjoyed it and wondered why I never ever saw any hair. She had told me that her mom had told her men don’t like it and her mom pair for permanent hair removal using her dad’s money as a highschool graduation and 18th birthday gift, of course he did not know. I could only be thankful for her mom’s forethought about my experience and her dad’s money.
The relationship got to the point where I was going to start looking at rings. I know she would say yes, we had already spoke about our future and babies. I did actually propose and she said she needed to wait to give me an answer, but she did confirm it would be positive, she just needed me to do the more traditional stuff like ask her father for permission. We planned a trip down south and I had over a month before I could ask and make her my fiancée.
The night before our flight she mentioned being nervous. I asked her why she was nervous about seeing her family. She explained that the last time she saw her parents in person it was not on great terms, but it was better now, they had made up. She explained more that when she was in college, she and another girl from her hometown had experimented together having lesbian sex. She ended up calling it a failed experience but one she was grateful for. When the other girl went home she told her parents she was a lesbian and that Ann had helped her discover that, everyone including her parents found out. Her parents got very upset upset to the point that they were going to disown her.
Ann had never told me this before, about her and another girl or about her parents being upset. At the time I would have been right along with them. I had been raised with more traditional values and Ann seemingly had as well. I was not her parent and we were not dating when it happened, so I attempted to make her feel better. I told her I understood that sometimes people make mistakes but she is on the right path now and we could get thru her misled past together. I thought I was being accepting of her mistake, I was wrong. Apparently she was not on the same page as me and she blew her top, she kicked me out and said something to the affect that is was not a mistake and that is it part of who she is.
A few years later I heard from a mutual friend that Ann had met and married a older black man. Her parents did come to terms with that, but only after she brought home their new grandchild.
That break up with Ann broke my heart, I was down and out for months. With my family helping and pushing me, at least remotely as they did not live with me. I did finally go out and meet a woman one night. Alisa was another girl way to good looking to be with me. She had DD tits, they were my favorite of any girl I had been with. While Alisa did not have laser hair removal on her pussy, she shaved it clean at least twice a week. She had straight long brown hair that she liked to have in pony tails. She did have a small little clit that stuck out a tiny bit when she was worked up, about the size of her pinky, that took getting used to but I loved her and it was sexy after I realized it was normal for some women. Her ass was the second best thing about her next to her milky titties. She had a cute bubble but, not fat or anything, just perfect. I loved seeing it in a thong. Any time she did anything slightly sexual my cock was hard.
I did open up to her about my prior experiences in love and loss. Amber who I did not know why she left me and then I told her all about Ann and gave her the specifics. Alisa was with me on my viewpoints and we had a lot in common. Even though I thought Ann was more traditional and conservative in her ways, Alisa was and she showed it. Alisa was a good church girl, she was active in the local political groups that aligned to my values, she understood the importance of the patriarchy and even discussed being a ‘Trad’ wife one day. She wanted to mother many children and do homeschooling maybe even living off the grid, the whole bit. I knew she was the right woman for me.
I got to the point where I worked up the courage to ask her for marriage. She agreed and we planned the whole affair. Alisa’s hometown was a few hours away but she planned to have a bachelorette party here. She drove home the weekend before to get her sister and drive her back to stay the week before the wedding and help plan the last minute details.
That Sunday afternoon I was expecting Alisa to show up with her sister. I had met her sister one time and I thought she was a nice girl, she had her head on straight just like Alisa. Her sister was almost as beautiful as her, but a few years younger and still in college.
Finally Alisa’s car pulled in and she came inside with a solemn look on her face. I was concerned and wondered where he sister was and what was with the mood she was presenting. She told me we needed to talk. I was getting worried, we had never had much of an argument, or a serious conversation like what she was possibly presenting. Initially I though she had some semi bad news, like someone died and we need to postpone the wedding, I was wrong, it was much worse.
We sat down on the couch and she explained that Friday night she went to the bar and had a few drinks with friends and her sister. Her sister left because her parents gave her a curfew. She said what happened after that started as a mistake and she did not mean for it to happen. I knew what she meant but I had to be sure. She had cheated on me and fucked some guy she met. I was not sure I could deal with a woman that cheated on me, but maybe it was something else.
I asked her if something happen that we can work thru or is it something worse. She told me we could not work thru this because she did not want to. She found out that she is not straight, she slept with her best friend from back home and she is with her now in the car, They are now together and our engagement is off and relationship is over. She said she was sorry and it looked like she genuinely meant it. She asked me to leave the house so her and her friend Sara could pack her stuff and leave.
I wondered why she wanted to leave, because this washer lease.
I was walking outside to my truck to go for a ride and I met a girl was walking in. This woman was a 10 as well, she had brown hair like Alisa. I was a man and I noticed her rack was probably a DD as well. She attempted to introduce herself and shake my hand, saying her name was Sara. I told her to fuck off and I walked past her to my truck. I drove around for 2 hours and went back. Alisa was gone by then and I went in and sulked for the rest of the night.
A couple days later I needed to tell my family not to come to wedding. So I called and talked to my sister and told her about my troubles. She was sympathetic and told me she would tell mom and dad. As we talked about me and my love life and how it always fell apart she said that Amber had messaged her and told her why we broke up. She had seen some anti-LGBT posts I made and could not date a homophobe. Now I knew what had happened to that relationship. It seemed that gay or lesbian theme was always a part of my breakups. Maybe I was the problem, maybe I was not accepting enough of the changing world. I mean, I am not sure it would have helped if I was an ‘Ally’ as they say with Alisa, but with Amber and Ann I would not have had those relationships end in those ways.
About 2 months later I decided I need a change of scenery, I was going to go back to Virginia. The lease was still in Alisa’s name and I had not been paying rent. I was still pissed at her, she was probably still paying it because she felt bad for me, but I wanted to get back at her. decided this would be a good time and method of payback. Leave the rental without notice and let her find out when the landlord called. I would just take what I wanted in my truck and drive home. I would get a job there. After the truck was packed, the rental still had a lot in it but I needed none of it. I did one last walk thru to make sure I missed nothing important. I left the door to the house open and drove out of town.
On the drive home, somewhere in Wyoming I had not seen a town for over an hour. I was getting tired so I decided to pull into the next town to get a bite to eat and grab a hotel. I got to the diner and sat at the counter. I had on a shirt from the college I went to. Luck would have it the guy I sat next to also went to that college.
He said, “Hi, my name is Jon, I went to the same school, did you go or you just wearing the shirt?”
I replied, “Hi, I am Tom. Yeah, I graduated a few years ago, when did you go?”
He said, “Oh its been a few years, let’s see…. I graduated 23 years ago.”
I said, “Nice, probably about the time my dad went there.”
We chatted and he told me he was headed west to home after finalizing a contract for the shipping company he started, Jackson Freight. He said he did not need to hurry home and was thinking about taking a detour to see some other sites as a sort of celebration to himself, his second in command was going to run everything.
About an hour later we had talked all thru supper and I realized it was getting dark, I said, “I need to get going and secure a hotel room.”
He said, “Me too, there is only one hotel in town so I will see you there.”
We got to the lobby, he was ahead of me, he got checked in and I was next. I was informed they did not have a room and that the man before me took the last one. I did not know what to do, my truck had no room to sleep and I was 2 hours away from the next town with hotel. On top of that I could not or at least did not like driving at night. I had seen a lot of deer during the day and knew if I saw them during the day the night would be worse.
I was in my car calling and confirming if I could drive and get a place, I was having no luck. Jon came to his car to get something and saw me frustrated on the phone.
He said, “Tom. What’s going on? Did you not get a room?”
I said, “No, they are all out, I am trying to find a place down the road but having no luck and I am not sure I would make it anyways. I am at a loss of what to do.”
Jon said, “Don’t worry, you can stay with me! There is no couch, but it is a king size bed, I trust you if you trust me. I am sure you have shared a bed before, and you wont even have to pay!”
I said, “Are you sure, I don’t want to intrude and you don’t even know me, or I don’t know you either I guess.”
He said, “I am not concerned you seem like a good kid. The offer is there if you want it. But make up your mind quick, I will need to head in, the mosquitoes are starting to get me.”
I agreed and we went in. His bed looked so comfy. Jon said, “I am going to take a shower and hit the sac ok son”
I said, “Sure thing, I will after you.”
He showered and came out in a towel. He was likely naked under the towel and I could see a bulge in his groin area. I don’t even know why I was looking of noticed it. He was pretty muscular and young looking for his apparent age. he must have been into working out and eating right. I hoped I could look like that when I was his age.
I showered and when I came out he was in his boxes finishing a phone call at the tiny desk. I was already in my boxers so I crawled into bed. I looked at him stand up and I was not trying to look but he had a large cock hidden in his boxers. Honestly it was probably as big as mine from what I could tell. His chest was hairy, but not too hairy, he had a six pack and his pecks looked good. It was the first time I had appreciated a man’s body. I felt weird and ashamed at my thoughts. I pushed that to the back of my head and ignored it.
He came over to the bad on his side and got in, he stated, “I normally sleep nude, however, with company I will keep my boxers on. I will live thru the discomfort, but you will owe me.”
I said, “I will buy you breakfast at that diner. I sleep nude most the time as well. I don’t want to cramp your sleep habit, if you feel more comfortable we have a blanket on, go ahead, I will be ok.”
He said, “Ok, you can too if it is what you are used to, I mean with the blanket and all.”
We both took off our boxers while the blanket moved with our arms moving under it. After that, I had a hard time falling asleep, he did not. About ten minutes in his side of the blanket was thrown off and the ambient light was enough to let me see his cock. Ashamedly I looked and it did look as big as mine, or as best as I could tell because of the low light and the fact that it was soft. I realized I was staring and my cock started to tent up. I felt ashamed and rolled over and fell asleep.
I woke up and realized I was spooning him. He was still asleep as much as I could tell. I started to pull away and he kind of held me there.
After a minute or two he slowly turned over and I said, “I am sorry, I don’t know what happened.”
He said, “I did not mind so much, but I have never had another man hold me.”
I said, “What do you mean when you said ‘you don’t mind so much’?” We were both still touching and he was still in my arms.
He said, “Look, we are both here, no one would know and your cock is hard, mine is getting there. I have never done this, but I am willing to see if I like it if you are willing to try one time to see what you think.”
I don’t know what came over me, I leaned forward when he stopped talking and kissed him on the lips. It was just the lips at first. Next thing I knew he and I had our hands pulling our faces together making out with tongue and all. His scruff on his face should have been off putting, but it was not. Our cocks were both hard and were rubbing on each other. We managed to pull away and I started kissing his chest down to the nipples. I sucked on each nipple as I played with the other one my cock was rock hard the whole time. I reached down and started to jerk him as I sucked is nipples.
I moved lower kissing my way down, his lower chest, then his hard stomach, I licked his belly button. I continued my trek lower to what I assumed I really wanted, finally I started to kiss the head of his cock. He was a little bigger then me, but not by much. I felt his pre cum on my lips, I used my tongue to taste it, it was salty and a kind of a sticky slime consistency. I knew I should no like it, but I knew I did. I put the head in my mouth, I sucked and tried to fit more and more in. I remembered all the blowjobs I had received from Alisa and what I liked. Ann had also blown me a few times, but she was never into it like Alisa, she was never as good as Alisa either. I tried all those things Alisa did for me, I wanted Jon to feel good.
I tried to not use my teeth, it was difficult at first, but I figured it out. I pulled back and kept the head in my mouth and worshipped his mushroom with my wet tongue.
Jon praised me, “Tom, just like that. You are doing so good. Keep it up and I will cum.” After 5 more minutes and me trying to suffocate myself with his mighty sword Jon said, “I am going to cum!” He did, I felt at least 5 good spurts and I actually wanted more of it, I caught most of it in my mouth. I was new and lost some of it, I swallowed down what I could before I lost more. While doing so I was trying to taste it so I could remember the taste. If this was a one time thing, I wanted to remember the taste, because I knew I loved the pre cum so much.
He was catching his breathe asked, “After I get my head back on straight from that amazing orgasm you gave me, can I suck you?”
I smiled and looked into his eyes and sweetly said, “That seems fair Jon.” He situated, apparently ready to go already and started blowing me with little foreplay. I was hoping for some nipple play like I had given him. About 10 minutes into his amazing blowjob, he was doing all the things I did to him, I said, “I am going to cum!” he pulled of and jerked me onto the bed.
He said, “Sorry I was going to let you cum in my mouth, but I got scared. I meant I did like the pre cum, but the full on sperm scared me.”
I said, “Don’t worry, I cant believe we just did that, can you?”
He said, “Never in a million years, it did feel good and I don’t think I feel ashamed, do you?”
I said, “Honestly, I am glad it happened. I am not ashamed and wont stop it from happening again, but I am not sure I want my family to know, if you know what I mean?”
Jon said, “I agree, I know my daughter has a soft spot for gay people, but I am not about to tell her I had sex with a guy, or that I am bisexual or gay or whatever.”
I said, “We are on the same page, that was fun! I liked it all, even the kissing.”
We leaned in and kissed groping each other’s bodies more. We rolled around and made out for another 20 minutes, we both got hard and knew we needed more release.
He asked, “Do you want to fuck?”
I said, “We probably should, but I am scared. Will you go slow?”
He smiled and looked into my eyes saying, “Yes baby, I will go slow for you.”
I said laughing, “So I am baby now?”
He said, “It felt right, I hope that OK? Maybe not in the morning, but like this.”
I said, “I think so, just weird coming from a guy.”
Thanks for reading pls vote or comment He replied to my comment as we got up into position, I was on all fours and he was on his knees behind me, “Me calling you baby felt weird. But somehow you about to be fucked in the ass doggie style by a man is not weird?” I laughed.
He slowly pushed his cock at my anus and entered, very slowly he went in and it hurt like hell. I knew it would eventually fell good, or at least not hurt. Once he bottomed out he started fucking my asshole slowly and increased over the course of a few minutes until we were really going at it. It felt so good.
I felt an urge to vocalize my desire so I said, “Fuck me daddy!”
That urged him on. He increased his fucking and I felt that in my balls. Without touching my cock with my hands or his I came with his cock fucking me. He came a few seconds later gripping my hips and forcing himself into me and me into him, the same way I always did when I fucked a girl doggie style and came in her. We collapsed on the bed, he rolled over and asked me, “Will you cuddle with me for a few minutes and then we should go shower. We actually need to come back and sleep.”
We cuddled with me spooning him, I kissed his neck and he turned over to kiss me. We started to get worked up and we both knew we needed sleep. We got up to shower. In the shower it was just as hot, I had showered with Ann and Alisa. So I knew very well that if two people shower together at least one person is getting off, or best case both. I had never showered with a man obviously, but we knew that if you are in the shower with someone, you have to touch and grope them the whole time. I fondled his balls and cock and he did the same. We both ended up giving each other a hand job.
Once we dried we laid on the bed and we fell asleep after some sweet kisses while cuddling naked again.
The next morning we got a knock on the door, he got up grabbed a towel and went to answer. I covered my naked body with the sheet and stayed on the bed. He talked to the maid and came back.
I asked as he laid down and and I started to touch his chest, “Was there an issue?” He laid on his back and I put my head on his chest playing with his chest more.
He said, “Not really we missed checkout, it is noon.”
I said, “Oh, I forgot.”
He told me, “I will just pay for another night, I am in no rush to get anywhere and this is a nice detour. You can stay as well, I don’t think you got much sleep last night.”
I decided to say something kind of kinky, “No, I did not get much sleep. My Daddy kept me awake!” I smirked and smiled looking at his face smiling back at me.
We kissed and ended up fucking the rest of the day and night. In the end I ended up driving back and moving in with him. He had an office and house in the city but his ex-wife and daughter lived mostly in his daughter’s hometown.
Thanks for reading pls vote or comment