Fourth Time is a Charm Ch. 02 by Bigguy7979,Bigguy7979 This is the second part of Tom’s discovery about himself. The story picks up after Tom had his first night of passion with a man.
We kissed and ended up fucking the rest of the day and night. In the end I ended up driving back west and not going home. I moved in with him. He had an office and house in the city, his ex-wife and daughter lived mostly in his daughter’s hometown. Our relationship developed and he had more sex then I ever thought possible, I know if I had been with a woman or is Alisa had not turned out to be a lesbian we would not have had this amount of raw sex. In no way did I ever want to go back. We got to a point two years down the road where we were comfortable being seen out and gay together.
I had not told my parents, but my sister visited once and she found out. She accepted it and said she was not only happy for me but proud of me as well for coming out to her as gay when I had been a bit homophobic in the past, ok a lot homophobic in the past. I never liked gays and treated the LGBT community as second class, sometimes worse then dirt. My sister saw me go from the person I was to openly embracing my gay sexuality. I even told her that sometimes I felt wanted to just be the woman in the relationship. I did not want to transition fully, but maybe cross dress and play the part. Jon had liked that the few times I wore lingerie to bed. I was not passible, but I thought I could be if I tried. Ashlee said once I tell mom and dad she would support me in a partial transition, like a top surgery and facial hair removal. That sounded great to me, I just needed to know that Jon wanted something like that.
Jon had told his ex-wife he was now gay but he did not tell his daughter. He saw her when he had business trips back in the area she lived, but I never joined. As it turned out his daughter came out lesbian about the time we got together. He said she would make it a big deal if and when she found out he was gay. He did not want their sexualities to be the thing that bonded them together. His ex-wife Samantha had remarried and divorced again since they split, she was not into monogamy as much as her husbands. She liked to sleep around, but Jon and her were friends again. At first it was for his daughter’s sake then later as someone to she and he could confide secrets in.
I had met his team at his company and no one seemed to care. He even proposed to me shortly after our 2 year dating mark. I said yes of course. We fucked like crazy that night. I took his load in my ass 3 times that night, he was full of passion and cum and I was full of his cum when we went to sleep. He always seemed to fuck me, I had fucked him one time and he said it was not for him. He usually gave me a reach around, but he also developed a taste for my sperm, saying it was his favorite meal. He was a great cocksucker, but I never told him that, fearing he would think it treaded on his masculinity. I know that seems weird, but he was a very bravado type man, even if he was gay.
He said we could have our wedding after his daughters. He did want to marry me and soon, but she had been engaged first and he did not want to outshine her special day. That made sense but I still had not met his daughter. He told me she was the most beautiful girl in the world. I could only imagine she was beautiful if she took after him in any way. He had no pictures around of her. When I moved in he was a true bachelor. Similar to me, he had the basics in his house and nothing else. Pictures would have been clutter and I was not really interested in asking for pictures of his family as I spent a lot of my time and effort in making sure we had lots of sex.
One day we got the wedding announcements for her and her fiancée. I got a shock, it was addressed to him and a plus one. His ex-wife had told her to put a plus one. It had rainbow hearts and the silhouettes of 2 feminine brides kissing the card said ‘Please join Sara and Alisa for their special day!’
I asked him fearing I already knew the answer, “Where did you say your daughter is from again?”
He told me the town but continued, “But the house is about 15 miles south closer to the river.”
This was going to be awkward. The woman who was the previous would be love of my life is marrying my current and true loves daughter. I pretended like I had not just got the shock of a life time and showed no reaction to it, other then a small amount of necessary excitement to be meeting his daughter and going to her wedding. I also was unsure how he would breach the subject of him being gay before the wedding in a month.
The next day we were cuddling on the couch, he was sitting up and I was leaned into him with my head near his chest and neck, I looked up into his beautiful eyes and spoke to Jon, knowing that time was not on our side. “Joh, baby, I need to tell you something important. I found out yesterday and it has been killing me.”
He looked from the game on the TV he had been watching down to my face, “What is it honey?”
I started slowly, “Well, it is about your daughter and her wedding.”
He sat up further and that forced me to readjust no longer cuddling, “Don’t tell me you have been with my daughter.”
I smirked and said, “No, not at all, but you saying that hits pretty close. I used to date Alisa! She was the one before you that broke my heart.”
Jon got a concerned look on his face, “Oh, I am sorry, I am sure Sara never knew and if she did I will have a talking to her.” He reached for his phone.
I stopped him and brought his hand back to me. “No baby, they are happy together and probably meant to be. Also, if I had not been dropped by Alisa I would have never met you.”
He kissed me and pulled me into a hug, he said, “I suppose you are right, but this will be awkward.”
I said quietly said, “Very much so, when Alisa and I were together she knew I despised gays and pretty much hated everything about them, now she will find out I am gay and will think I am a hypocrite.”
He said, “Well, from what Sara tells me, Alisa was the same way. I mean we raised Sara to be accepting and all but she tells me Alisa’s family is not that way and did not raise her that way. In fact they are not coming to the wedding.”
I agreed and said, “If Alisa made the switch from where she was at with her ideology, I don’t see why she should be upset about me doing the same, I think you are right.” I added, “That sucks her parent’s are not coming, I know she loved the idea of having her sister at her wedding.”
Jon smiled and said, “Actually I remember Sara telling me that Alisa’s sister would be there.”
I said, “Good, even though I hated Alisa initially for what happened, I am glad she is at least getting one thing her way for the wedding.”
Jon kissed me and pulled me onto his lap so I was straddling him close, gripping my ass and pulling me into his hardening cock. “Well, we will call them to meet this weekend, we need to make sure they know before the wedding, and since we wont have as much time to fuck this weekend, I will take your ass now!”
I kissed him and started unbuttoning his shirt. After kissing him a while I broke away to say, “I like that idea Daddy!”
We had about 10 minutes of foreplay and then he had me bent over the couch fucking me like a dog in heat both naked as the day we were born. He said, “You like your Daddy fucking your tight asshole son?”
I looked back at him and locked eyes to say, “Yes Daddy, fill my ass with your potent sperm, make me pregnant!”
He slapped my ass hard, probably the hardest he ever has and he came in me, I felt him spurting shot after shot in my boy pussy. I ended up coming on the couch as well. I said, “Wow, that was intense, I guess I need to get a towel and clean it up.”
He started walking away, content in having just came in my asshole. I cleaned up and straightened the house up for bedtime. I put on some pink panties as I had started wearing to bed recently. He had just finished watching his game in the bed and was shutting the TV off to go to sleep.
He saw me walk in and smiled at me and said, “Wow, baby, you look sexy, but I am not sure I can give you another load tonight.”
I crawled into bed and cuddled up to his naked body, “Don’t worry baby, the load you gave me is still in me. I am good.” I worked up the courage to ask him something I had been wanting to, “Babe, I know you love me and since I don’t have much to do tomorrow, I was wondering if I could go down to the sex shop while you are at work, I want to get something to surprise you with when you get home?”
He said, “Of course honey, you don’t need to ask me though, why would you ask?”
I said, “Well, I want to make sure you would be ok with a change I want to make to my style.”
He smiled and caught on, “Oh, you want to wear feminine clothing again huh?”
I asked, “Does that idea excite you?”
He said, “I like it a lot. Is that it?”
I told him, “You will have to wait and see.”
The next day I went and bought a sexy French maid uniform. When I got to the car I looked closer at it and thought it was too cheap. I wanted something better quality. I mean this would do for one maybe two good fuck sessions, but not if he was rough, or if I actually wanted to wear it at home. I decided I would order a higher quality online. When I got home I ordered several higher quality uniforms and also some fake breasts to fill it out.
I had ordered, a pink maid uniform, a black maid uniform, both would not barely cover my ass. I frilly pink dress, a brides dress with lingerie, a police uniform, a school girl outfit and a cheer outfit. The last 3 were likely only for sex, but the dresses and maids uniforms I would wear at home. They would most likely lead to sex, but before my man got home from work, I would like to wear them.
I took a bath and removed all the hair from my body. I massaged lotion into my skin and did my makeup and put a wig on. That night Jon got home and caught me cleaning the coffee table in my cheap black French maid uniform, I was without panties and he closed the door and moved to me while taking his pants off, he got to the floor and breed me so quick.
He fucked me in that outfit 3 more times before the weekend, destroying it the last time. I told him not to worry, I had better stuff on order.
That weekend we made the trip to meet Alisa and Sara. He met Sara alone initially and I stayed in the hotel. Jon told Sara he was gay and that his lover was Alisa’s previous lover and I was waiting at the hotel. He told her we would all have diner at her house. He told her to give Alisa a heads up but there was no hard feeling, we just needed to meet and break the ice that had formed. She took the news of him being gay well, as expected. He said it was hard to read the other surprise he told her.
Jon and I sat on the couch in the hotel talking and I told him I was nervous. He turned to me and said. “If I gave you a blowjob you that settle your nerves?”
I told him, “I am not horny right now.” Some men are always horny I swear.
He said, “Well that is new. Maybe later tonight huh.” He kissed me and we got up to leave.
We got to their house and Sara let us in, “Dad, glad you came, and Tom lovely to meet you again.”
I said, “It is nice to meet you this time, sorry about last time.”
She said, “Well, we can discuss later, but water under the bridge I hope.”
I smiled and said, “I think so.”
Alisa came around the corner and saw us, she came right over, probably trying to just get the awkward introduction out of the way. She was like that. “Nice to meet you Mr. Jackson, and its nice to see you again Tom. I am glad you guys are here.” She hugged Jon and me. The hug was awkward, but not a bad awkward.
I said, “Alisa, you look great as ever.”
With that out of the way the rest of the evening was easy. We talked over diner and Alisa told us about how she got blindsided by the lease issue and had to shell out a ton of money, I offered to pay her back and she said she did not need anything, she deserved it to some extent. I disagreed but we left it alone.
Later Sara and Jon left for a evening walk while Alisa and I talked.
I said, “This is weird, not just the coincidence, but the fact that we ended up in these types of relationships.”
Alisa replied, “Oh, you mean how we were 100% straight and not warm towards the LGBT community?”
I affirmed her comment, “Yes, do you think it is weird, that I like being with a man?”
She said, “Well, I am sure you were surprised and upset when you found out about me finding a woman.” she added, “Most guys would probably ask to watch as a consolation prize, but I knew better at the time about where you were at.”
I was shocked I asked, “So if I had not been so homophobic you would have let me watch?”
She said, “Probably yes, but you have 2 things riding against you now so don’t ask.”
I said, “Let me guess, the fact that I am gay and the fact that you will soon be my step daughter-in-law.”
She replied, “Yep!” and laughed.
I said, “Well, the step daughter-in-law think is a deal breaker, but I do enjoy straight and lesbian porn, so does Daddy.”
She coughed and laughed, “Wow, you call him Daddy?”
Embarrassed I said, “Well, that slipped out, but when the moment hits I do, and I am not ashamed.”
She surprised me and said, “Well, you should not be ashamed, I call Sara Mommy as well in bed. She sometimes calls me mommy too.”
I changed the subject, “So, getting married, I know you always wanted kids, is that still the case?”
Alisa confirmed, “Yes, we are going to have kids, both of us, we are going to use the same sperm donor. We still have not settled on the race or a specific donor yet. She wants a white donor, I want a black donor. But I think my reasoning is to piss off my parents so…”
I said, “Are you guys doing the natural way or like insemination?”
She quickly said, “Insemination, neither one of us want anything to do with a cock.”
Just then Sara and Jon came in, we got some wine and drank, we drank too much to drive. It was time for bed.
Sara offered, “Since you cant drive, you two can stay in the guest room.”
Alisa added jokingly, “But since you are not wed, keep it Christian in there, no sex before marriage.”
Sara added, “Or don’t, we don’t mind the noise as long as there is love we are all happy.”
Jon stood up and said, “Well, Tom let’s go, and try to keep it down I suppose.”
We went in and actually did not make too much noise, we 69’d and after we came and swallowed we fell asleep in each other’s arms. We did hear moans coming from down the hall as we fell asleep.
Their wedding was great, Ashlee came as well because she knew Alisa from when we dated, Alisa said it was ok. After the wedding Ashlee stayed with us for a few weeks. She never cramped or style. I wore my dresses during the day and she helped me with makeup. When Jon got home we did go to the bedroom immediately for a hour or so each day. She knew we were fucking, but she did not mind.
Thanks for reading pls vote or comment