Long Journey

Since I was 16 I was fucking the older woman down the street. She was plump but nice and tight, she taught me all, and let me have her in all three holes. The price I paid was letting her husband fuck me and get sucked by me. She would have gangbangs with guys he brought over and I joined in a few of them, always staying the night with her or him so I could have a few beers too. After a few months we had a gangbang and I was the choice for the night. The wife went out for the night. It was the first time I'd sucked anyone other than the husband and the first time I had anyone else fuck me. I took 5 guys plus him that night multiple times. I was pretty shy since he had me in stockings, heels, garter and a push up bra. The see through panties didn't last very long before they were tossed somewhere in the house. Being shy about it I wanted to be in one of the bedrooms and they guys come in one at a time. They agreed but only after the husband fucked me once in front of them all.

Flash forward another 6 months, I'd entertained a few of his friends by now, and I dressed in womens underwear even if I fucked the wife. She liked it, and I must say my small frame and waist (5ft.9in. 135 lbs) made me feel nice and with help in make up, longer hair I looked like a girl pretty much. They had a rich friend coming over for a long weekend, and had me stay with him in the spare bedroom now with no parents living with grandparents this was easy to do. I was to be his girlfriend for the time he was there. When he arrived, I was in my usual ladies underwear with a sheer robe. We went into the bedroom to unpack and after I got on my knees and he pulled out the biggest cock I'd ever seen. Nothing in porn videos or pictures was like this. It was thicker than my wrist, and about 10 or 11 inches long. It was difficult but I got him off. I was scared to go to bed with him that night, but I did. It took a while to get him all the way in me, but half way through his first time with me I was in heaven. I can say I truly loved getting fucked by this massive cock.

I got fucked three to four times a day by this man and I was falling for him. He bought me outer clothes, my own makeup, and bought me j*welry. I honestly for the first time felt totally feminine and acted like it now. When he left, he said he'd send for me. In three months I was on the west coast and enrolled in college, full tuition paid, and living in a huge mansion driving a jaguar sports car. Throughout the time, I started cooking meals for us, the staff cleaned the house, We went on trips and did everything a man and woman couple do together, including making love, yes- sometimes fucking, but making love. I was in love. I wanted to be his wife, his woman. He took me to a doctor and I started hormones, my clit shrunk to about the size of my little finger, my figure blossomed as did my boobs. I was in heaven, all my clothes, bikinis, lingerie were womens. We had 5years together before he died. I inherited everything from him. The house, the cars, millions of dollars, even more euro, he always gave me very good investing advice and I followed it.

The thing is, I don't know if I want to be a woman for anyone else. I went back to my hometown and visited the couple that started me on this road, and she was so jealous, she didn't want him touching me at all. I wasn't there for sex anyway. I will go to the doctors and see if I can reverse things and be a man again. Granted a man with a well worn backside and mouth. I think I'd rather see women now, and never tell about my past so I can keep what we had between us and only us.

I know this is going to get a lot of "remove" tags, but I don't care. I just wanted to tell someone how wonderful it was being male, then female, and ????

Comments

Anonymous

by Anonymous on Aug 22, 2022 at 3:44 PM

Good for you. Whatever choices you make, hope they make you happy. You deserve to be happy and feel sexy and comfortable with whomever you are.

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Anonymous

by Anonymous on Aug 22, 2022 at 4:08 PM

I was excited to read this story. But, gave up. It was kinda long. My eyes started to water and cross mid way thru the story.

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Anonymous

by Anonymous on Aug 23, 2022 at 12:12 PM

I hope things work out for you, but there is always the chance that the changes caused by the hormone treatments are not fully reversible. Your cock may not get back to its starting size and might not get as hard as you recall, even after taking loads [no pun intended] of testosterone.

Also, after five years of being a bottom for a well hung man, you may have developed a submissive libido and find you want to continue using your well worn backside and mouth to service another big cocked man.

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