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Getting Used to Dildos

"The journey to using dildos anally"

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Lucy had always wondered about having anal sex. Did anyone really enjoy it? When she first started thinking about it, the internet wasn’t like it is now. Apart from asking others who had had anal sex there was not much she could do to find out.

The first thing she knew was that she had to see if her fingers would feel good inside her. She used to play with herself whilst kneeling down so this would be a great way to start. She decided to slowly stroke her hole with her wet finger and see if that felt okay. Gradually she gently slid her finger inside. It only went in a little bit and it didn’t feel that good. In fact, she just felt like she wanted to go to the toilet.

‘How could people like this,’ she thought to herself.

Lucy knew that people had anal sex and enjoy it. She decided to keep trying to see if the uncomfortable feeling would go. She kept persisting with her fingers and it did start to feel a little better, but certainly not sensual, yet.

She thought about trying with something that was cock shaped and found something that might do. One night she got herself ready and put on some sexy stockings and a Basque. She used some baby oil and started sliding her make shift toy inside her hole. It did feel a bit better but she still had that feeling afterwards. Not wanting to give up, Lucy kept trying.

One night, though, she made a bit of a breakthrough. She had found something else that was a bit larger and was on her bed, kneeling dressed up and feeling really horny. She started to writhe up and down but the toy only slid inside her an inch and a half. She wasn’t completely hard but was gently rubbing herself anyway.

Then she had the idea about seeing how deep inside her she could push it before it hurt. She lowered herself down steadily and it kept on going in deeper and deeper. Then, to her total amazement it suddenly went past a point and slid in another two or even three inches.

“Oh my god, that feels incredible. Wow!” she thought to herself and moved up and down slowly but surely. She still wasn’t fully hard, but then to her total surprise, she came. Almost instantly she realised that there was a G spot inside her that was so sensual that it could make her orgasm, without any other stimulation. The feeling of wanting to go to the loo had gone too.

As the weeks went by she tried it repeatedly, eventually it became something she just couldn’t stop doing. Lucy plucked up courage and went to a sex shop in a nearby town. She was very nervous. She knew that a guy walking into a sex shop and buying a dildo was going to give the game away. Lucy was her male self and just looked like a normal guy. The shop keeper would know that it was for him. It did give her a feeling of excitement that someone would know that he was going to have fun with a dildo. Lucy started looking at the dildos.

Seeing a big selection in front of her, she was a bit unsure what to get. She just didn't know 'how big', 'realistic' or 'smooth'. Lucy stood there totally bemused, when suddenly she noticed a realistic dildo with balls, veins, and helmet. It was about six inches long. This was the one for her and she didn’t even care about the price. She just had to have it. So off to the counter she went, shaking with anticipation and desire. Before she knew what had just happened, she was driving home with this toy on the seat beside her.

When she got home she couldn’t wait to have a go. She opened the packet and kissed her new toy. Taking out the baby oil, she spread it all over and positioned herself. As she pushed her body down on the wonderful helmet, she really felt it inside her and it went deep.

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She could really feel the contours of the helmet and the veins. In and out it went and then suddenly, she orgasmed. Having something that felt like a real cock inside her was amazing, the sensation was truly awesome.

Lucy used that toy quite a while and then over the next couple of years replaced it with other toys. They seemed always to be getting bigger. She felt that she needed more stimulation and wanted to get a larger, thicker toy.

She eventually got this eight inch cock with a five and a half inch diameter. Desperate to give it a try, she couldn’t wait to get to bed. This was quite a bit bigger than her other toys, so she knew she would have to take it gently. Lucy had to work herself up with the other dildos first, to get herself really relaxed. This was probably not an anal dildo, as it was really big. Could she actually get it inside her? After fifteen minutes of trying she stopped and realised that it was just too big. Her hole couldn’t take something that massive inside.

Lucy did feel frustrated and a bit upset. She so wanted to use this new gift and tried again that night. It was no good, it was just too large. She kept trying but to no avail. After a few weeks of leaving it alone, she decided to have another go one horny night. She started with her other toys, really working them hard and quickly in and out so she would feel really relaxed. Ten minutes later she thought she was ready and went for it.

At first, she encountered the same issue in that it was just too big to get inside, but she persisted. In and out, a little further all the time. Then with an overwhelming sensation throughout her whole body, it slid deep inside her. She stopped, gasped and just lay there resting, getting herself relaxed with this huge cock inside her. Then she moved it slowly out and then in again. She’d done it. It felt wonderful. As the pumping got more intense she really started to feel so sexy, sensual and then very quickly the moment arrived. She came all over her stomach.

The next night she wanted it again. This was really good; so good that she couldn’t wait to get it inside her. Lucy had always used her toys and played with herself with the light on. Often in front of the mirror. She wanted to know what it would feel like to just be naked, with the lights off. Laying on her bed with her eyes closed, she wanted to just enjoy the sensation.

Well, as you can imagine, it was sublime. Over the next two weeks, every single night she lay on her bed with the lights off and closed eyes and fucked herself like mad. The more she used it the better it got. Within a few weeks she didn’t even need to start with the others to warm up. She could start with this one and she increasingly got so much pleasure out of it.

Over the next couple of years she actually went for something even bigger. She ended up settling on a toy that had a seven and three quarter inch diameter with a really large protruding helmet. Lucy went through the same process with this monster. This was really big. After four days of trying she did it. It felt even better than the last big one she had used. She used to look at it and get hard just seeing and knowing that this huge dildo was going to be inside her. An incredible sensation. 

So, this was the anal sex feeling. The dildo, being rammed inside her hole was truly amazing. The inner G spot was so stimulated by these toys that she came every time. The orgasms were different too. Now she knew. 'Yes, anal sex is fantastic and I know that it feels wonderful.'

Anal sex was awesome and Lucy has been using her toys night after night for a few years now. She loves every second of it.

Published 
Written by LucyLou62
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