Sunday, September 9, 2012

Thus I lost my virginity

In my last post I mentioned that V's strap-on had arrived and that she had told me that last night would be the night when she would take me with it. This is the account of how it happened.

The day passed slowly, because I was waiting, expectant. V had to go out and had asked me to prepare dinner for her before she came home. I tried, I really tried, but there were technical difficulties, so I could not finish the job. As soon as I realized that dinner could not be ready as I had been told, I texted V and told her. She understood, and told me that she would take care of the problem when she returned.

She came and brought what I needed, and asked me to fix the partially made dinner while she did other things with the girls. I did.

After dinner was served and mostly eaten, V approached me and told me that in her experience, that things I was about to do would take about half an hour. I didn't know what she was referring to, so I asked. She was talking about the enema she knew I was going to have, so I explained that I had already done it. She seemed a little put back by this, so I asked her if she wanted to be involved, but she reiterated her previous "no way!"

After all things were done, she told me that she was going to the room and that I should follow.

Once there, she proceeded to take her clothes off, but kept a pair of boy-short panties on.

"What are you looking at?" V asked.

"You are so beautiful," I said, in all honesty. I think she is the most beautiful creature alive.

"I saw the way you were looking at me," she said. "I know you are wanting me, my mother warned me about men like you!"

"What did she say?" I asked, following along.

"That I should make then do my bidding," she said. I felt a little tug on my crotch as she said that.

"What would you have me do, Miss?"

"Bend over."

I walked around the bed and gave her the strap-on, which was hidden in my drawer per her instructions and she put it on while standing in front of the mirror. Seeing her adjusting the straps and knowing what was to come made me weak in the knees.

After the strap-on was properly adjusted, she turned around to face me.

"Do I look fat?" V asked.

"No!" I said quickly.

"Good answer," she said approaching me. "Take your clothes off."

I did. My hands were shaking.

She approached me and kissed me, rubbing her silicone dildo against my hard on.

"I don't know what to do," she said. "I'm nervous."

"I'm nervous too," I said. "But it should be okay."

"Are we going to lubricate it or something?" She asked.

I gave her the lubricant and she placed two drops on the tip, then rubbed it into the shaft.

"I should have made YOU do this," she said, her hand moving up and down her shaft in a masturbatory fashion. "This should be your job."

"I'm just going to lay face up and let you ride it," she said pulling me towards the bed, but as I approached, she pulled me past her and pushed me against the bed.

"Bend over," she said.

I obediently did and she pressed herself against me, holding me in place.

"Is it here?" she asked twice, making adjustments until the third time, I felt the head of her dildo pressing into my outer sphincter.

"Are you okay?" She asked when the dildo suddenly went a little into me.

"Yes," I said. "I'm fine."

She kept pushing and pulling little by little, asking me with each and every thrust if I was doing fine. I reassured her that I was fine and that I would let her know if I had any problem.

"Sorry," she said. "I'm killing the mood. I will stop asking questions."

The dildo was further in, three-quarters or so, by my estimate (I could not see it, so I may be wrong) when she asked me another question.

"How deep should I go?"

"Go all the way, honey." I said.

After that, she didn't ask anything else. She began to push harder, until I had taken the whole length of the dildo in. Then she began to pump in and out while scratching my back and keeping me firmly pressed against the bed.

"This is sexy!" She said as I moaned in pleasure and moved my hips back and forth to get more of her dildo inside.

I got tired relatively fast, because I was standing on my tip-toes, so I asked her if we could climb on the bed. We did and she took me from behind again, doggie style.

This time, she went straight for my anus, finding it easy and went all the way inside in her first attempt. I guess that me being on all fours probably gave her a better view of her target. She used her hand to go around and stroke my penis. After doing this for a bit, I felt that I was about to come and asked her if she could stop using the hand, because I wanted to see if I could have an orgasm from the anal action alone. She agreed, and continued pumping my ass until she got tired.

I then told her that I could ride her, as she had suggested earlier, and she went face up. On this position, I had a hard time getting the dildo straight into my anus, and it came out twice. It also didn't penetrate far enough, probably because the bed is too soft and we kind of sink into it. I think that in order for this to work, a pillow needs to be placed under her hips.

The other problem with me riding her, is that I'm larger and it feels very awkward for me to basically fuck myself that close to her face. She didn't seem to mind, though and bit on my nipples while we did it. Again, if the dildo was going in deeper and not coming out, I think I may have had an orgasm on this position.

We went back to the first position, this time at V's request. She told me that it was the easiest for her and she fucked me until she got tired, at which point she pulled back and told me that she was done for the night.

"Turn around," I said breathlessly.

This time it was her turn to misunderstand, so I clarified.

"Turn around and take this off" I said, helping her take the strap-on off.

Then I grabbed her and pushed her against the bed, in the same position she had been fucking me.

"Oh no," she said. "You are not going to enter my ass!"

I was already going into her vagina, so she stopped arguing.

"Oh, baby," she moaned. "You are so much better at this than me!"

"I've had some practice," I said.

I apologized in advance because I knew I was close to orgasm, but she said that she was close too and actually managed to have hers just before I had mine.

All in all, it was a beautiful experience. We had a discussion afterwards and the following points came up.

ME:
  • I loved it.
  • It was cleaner than I expected, probably because of the earlier enema.
  • I felt grateful
  • She crossed a line that no woman had crossed before (with me).
HER
  • She loved it.
  • It was easier that she expected. The strap-on held surprisingly well.
  • It was better than she expected because she thought I'd come right away, but I didn't and she got hers as well.
  • This is like having the best of both worlds.
  • Next time she will go open crotch.
  • She wants a dildo that is actually bigger than my penis (uh-oh!)
And this is the tale of how I lost my virginity.

1 comment:

  1. Thanks! I do think it was awesome as well, but my mother taught me not to brag ;)

    ReplyDelete