So this is going to be quite a long story because it goes a long way back. So Jesse (not her real name) was a 5′ 3″ slim brunette and we were about 18 years old when this all happened. We’d been friends for quite a while before we decided to take things further. Jess had quite strict Christian parents and was quite shy in general. Always wore long sleeves, always wore long pants and never swore.
One day we were talking when I asked the question “So when do you wanna have sex?”.
“Oh I think we should wait till after marriage” she said.
“Wait you’ve never had sex?”
“No” she blushed as a smile crossed her face.
“But what do you do when you’re horny?” I asked
“I do nothing, I guess”
“Wait you don’t masturbate?”
“What’s that?” she asked.
“Do you rub ur vagina for pleasure?”
“Oh isn’t that a sin or something?” she questioned.
“No most girls ur age have done it by now”
“Really?”
“Yes how come you never got curious and tried it?”
” I guess I never really thought about it and even if I did I was too scared to try”
“Here let me show you”I asked her to take her pants off revealing her perfectly toned thighs wearing big white granny panties. “OK now point you’re finger to the top of ur vagina and make circles with it” she copied “like this?” “yeh that’s it”. “It feels really good” she smiled and blushed a lot. Her panties began to get a big wet stain on them so I asked her to take her panties off revealing her perfectly formed virgin vagina. It was a neat tight slit which was now ragingly red and soaked.I asked her to lay down but she kept her baggy long sleeve top still on (she daren’t take it off) and continued to masturbate. By this point she was bucking her hips and moaning a little.
“I feel like I need to pee” she exclaimed.
“You’re not going to pee just keep rubbing” I tried to reassure her.Then all of a sudden her whole body arched back, she screamed a little and her legs quivered with pleasure. A stream of cum ran from her pussy as she laid back down blushed red and sweating with exhaustion.
“That was amazing” she smiled quietly as she rolled over and went to sleep.”Now promise you’ll do that every morning and ever night for me” I said wanting her to get good at it.”Yeah I promise”
The next morning true to her word she text me saying “I did it again it was just as fun. Thank you for teaching me this. xx”
We continued this for the next month teaching her different techniques and how to finger inside. We started teasing each other with swapping suggestive pictures which soon turned into nudes then eventually full videos of her doing it. It’s fair to say she got pretty addicted to it.
So I bought her a toy.I didn’t want to get her anything too extreme at first so I bought her a small bullet vibrator. I was with her when she first used it.
By this point she was comfortable being fully naked in front of me. Revealing her perky little A cup breasts and sexy lean abs which pointed down toward her vulva. She put it on her now super sensitive clit and immediately folded her head back. She looked at me in a trance
“woah why didn’t you tell me about this before this feels amazing”.
It wasn’t long before her whole pussy started spasming and legs were quivering as she came hard.
She stopped. “Keep going” I said. “Wait what?” “You’re not done yet keep going”. “You didn’t tell me I can have more than one!”For the first time in her life Jesse was having multiple orgasms. By about half an hour in of pure pleasure she asked me to hold the toy for her. This time she not only spasmed but pee started spurting out her pussy too. “What’s happening am I peeing?” she asked. “No you’re squirting” “It feels so good”. After the squirt she was too sensitive to continue and once again slept with a huge smile on her face.
The toy became her new favourite thing at one point she said “I think I love this toy more than you” I laughed. She’d practiced with it everyday sometimes for hours on end. Sometimes she’d take it to College with her and use it in the toilet she loved it.
But outside of our relationship Jess was still quite a shy reserved girl but that was all soon about to change.
The first time we had sex was about 3 months into our relationship. It was pretty standard apart from the fact it was her first time but after she’d got over the fact she was “sinning” we tried to have sex multiple times a week. She loved being eaten out too not so much anal.
In about the 4th or 5th month our relationship took a turn for the worse. She said she was getting bored of me and felt that she’d done everything she can and would rather have new experiences with another boy. “You don’t love me?” I asked. “Well I like the time we had together and thank you for introducing me to sex and stuff but I just need something more I can’t explain sorry”. “There is loads more fun things to try just give me a second chance and I’ll show you”.
The next day I bought her a remote controlled vibrator and left it on her bed with a note saying “wear this”. I had the remote. When she got talking to Zac the hot muscular gym dude at our college I turned the remote on making her blush and and bend over. She turned to me with both anger and embarrassment.
“What are you doing I thought this was for later?” she said naively.
“No it’s for now. I know you want Zac to make you feel this way so I’m just speeding up the process”.
“You want me to cheat?”.
” I don’t mind who you fuck but you’re not going to get any boy dressed like that”.
“Do you want Zac” I pressed the button. “mmm no”. Do you want Zac. I pressed the button again “hmmm stop no”. “Are you sure you don’t want Zac?” She bit her lip. “You don’t want him to pound you hard every night non stop till your a withering sweaty mess”. I kept the button on and by this point she was moaning loudly and visibly cumming in front of me in public thinking about Zac.
“Ok you got me I like him”. She said catching her breath. “You’re not bothered by it?” she asked. “Not really If I get to help you get with him then you have to let me join in.” “Join in how?”. “You let me watch maybe film it or something?”. “OK deal as long as you’re the only one who sees it”. “Deal”.
We went shopping for an entire new wardrobe and threw out her old baggy nun clothing away. She could now only wear crop tops and hot pants and the odd skimpy dress. The first time we went out she looked amazing even girls were complimenting her “I love your new style”. She said “I hate it I feel like everyones looking at me”. “They’re looking at you because they find you attractive” I said. “Will this work on Zac?” she asked. “Hmmm maybe not yet”. So I taught her how to flirt. I started by getting her to practice walking up and down in heals by showing her videos of catwalk models doing it. She was a little shy but she sort of got the hang of it. Next we went to salsa classes together which always made her super horny. Finally I got her used to talking to other boys at the bar but as soon as they tried to touch her she went straight back to me out of fear but it we had a laugh over it. After a few months I said she was ready.
We’d set up a load of cameras and she’d invited Zac to hers for the night. She was wearing a skin tight red dress and no bra or panties. This I got from the video. They sat awkwardly on the couch. “So what do are you like in the bedroom” she said doing just as I’d taught her. She touched his knee. “I’d do you hunny” he said in his typical douchebag way. “Let’s do it then”. They made their way to the bedroom and this hunky guys with nice abs fucks my gf hard for about 10 minutes before he cums and leaves.
“So how did it go?” I texted the next day.
“It was ok” she said.
“Only ok?”.
“Yeh I made a nice video for you” and boy did she.
When I saw it I suggested she make an Onlyfans because she was that hot. “But I thought only you wanted to see it?”. “Girl if you can make money doing what you love then do it”. “Haha but I love you”. “I know but I know you can get bored of me so I’m cool with letting you do a different dude every night if you like.” “Thank you so much, you’re the best boyfriend ever!”She agreed to do it but only if her face was blurred and sure enough she did it every night with a different dude.
The oldest man she got was in his 50’s and he was so rough. She said she loved it rough though. The biggest cock she had was this black man who was about 10 inches she thought she was going to be too tight for him but she rode him on top and managed to slide it all the way to the base of her vagina that sparked her interest in buying huge dildos.
Eventually the guys on their own weren’t enough and she asked me to join in making it a threesome. She loved double penetration.The best time was when I asked her if she wanted to try a girl. So we invited her friend Sophie a 5′ 8” redhead with D cup boobs over to come eat her out. She was a lot less creeped out by a girl than she was the dudes and she loved it really letting loose. That became a weekly thing in the end and we bought her stap ons and dildos to go with it.
Eventually her Onlyfans built to the point that she could afford things like a hitachi wand which made her squirt every time. That lead onto a Sybian which to this day when she’s not fucking she’s riding pretty much. Then I also got her a fucking machine because she likes it rough and it makes her cum so hard.Nowadays we do a lot of swingers clubs and group sex. Her parents kind of disowned her but she’s having the time of her life. She tells me that she wishes she wasn’t so inexperienced for so long. So yeh any questions just ask.
Source: reddit.com/r/gonewildstories/comments/sv4ej7/changing_a_girl_mf