Update: My (f)irst wild fuck with a coworker..with pictures [M/F]

This is a follow up to my first wild encounter with my coworker that I posted last weekend:

http://www.reddit.com/r/gonewildstories/comments/3378b3/my_first_wild_fuck_with_a_coworkerwith_pictures_mf/

After that encounter, we sexted, texted and fooled around a few times. We did not do it again until I met him on the last Friday of March for happy hours. He broke me the news that he was leaving. He went on a vacation in February to meet his daughter who stays with his wife. Apparently he wanted to be more closer to her. So, he took a job in the nearby city so that he can meet his daughter more often. I told him that he made the right decision.

Then he asked me if I want to do it again. I said yes. He told that he wanted to do anal and like he said during our first fuck, he would regret if he didn't do that. I told him that I have never done it and I am not sure if it is right or wrong. Actually, I never had to even think about it before as none of my previous boyfriends wanted it. He said that it might be something I should thin as my next boyfriend might ask for it. He suggested that it might be a good idea to try with him and come to an opinion. I suggested jokingly that we should do it in the trial room. We both laughed and had drinks and chatted with our colleague.

I thought carefully and what he told me kind of made sense. What if my next boyfriend wants it? How should I react? I could safely say that I am not into it. But I was also a little curious especially after he praised my ass. May be some asses are too good and that might prompt men into having anal. All this might sound absurd or border line funny, but that is what went through my head. I decided to try it. Besides, I was comfortable with this man. He was also a little experienced. And I also will not be seeing him again. So, it made sense to me. I met him on the following Monday and said that I want to try it. He was very happy that I agreed. Over the course of that week, we discussed when we should do it as it might take more time. We decided to do it at my place that Saturday. We had two weekends time as he was leaving in two weeks.

He came to my house that Saturday evening. I poured him some wine and we chatted a little while watching TV. Apparently he watches game of thrones and was very excited by the new season. He got an anal training kit with him. It had a lube, fox tail and a couple of butt plugs. He previously gave me a vibrator when we first met. He told me that he likes toys and they add to the variety. He stood and removed his pants and tee. I could see the bulge. He asked me to stand and then strip my pajamas. I did as he told. He asked me to sit beside him and then we started kissing. His hand slipped into my panties and he was sucking my boobs. He was alternating between sucking my boobs and kissing me. Then he slept on the couch on one side while I sat on the other side. He spread his legs around me and looked into my eyes. I opened his boxers and started sucking his cock. He loved getting sucked and after a few minutes he slowly changed position to standing while I was still sucking. Then he asked me to sit on the sofa leaning back. I thought he would fuck me. Instead he came on the other side of the sofa and put one leg on sofa and started face fucking me. He held my head tightly by my hair. He fucked me like that for a few mins. He switched his position and sat between my legs and started eating me with the fingers of his two hands pinching my nipples and squeezing my tits. I came and he kept eating.

After that he asked me where my vibrator was. I said it was in my bed room drawer. We went there together. Then he asked me to lie on all fours at the end of the bed. I knew what was going to happen. I said to him, "I am nervous!". He told me, "We will go slow. I will not hurt you". I smiled and took the vibrator and positioned my self on all fours. He asked me to masturbate while he oiled my butt hole. The feeling of oil there was very new. He slowly started oiling my hole and he slipped his oiled index finger inside. I was masturbating and the feeling was very very new. Next he slipped both his fingers and it felt a little uncomfortable. I told him the same. He asked me to stop only if it hurts. Then he got the fox tail and slowly inserted the plug. The feeling of the plug getting into me was very weird, new and funny. It hurt a little but by the time I asked him to stop, he was done. He said, "You are now officially fox tailed". I said, I wanted to pee and went to the bath room. He followed me, asked me to kneel and took a picture (http://imgur.com/UeQ7E4h)

When we came back, he asked me to lie on the bed on my stomach. He caressed my butt and spanked a few times on either side. He said, "I am gonna fuck your brains out". By that time, I already came twice and was butt plugged. He slipped his fingers into my pussy and said, "You want it. Don't you?". I said "Please fuck me now!". I was aroused. He was on his knees with my ass in front of his dick. He held my hair and penetrated into my pussy. I gasped. He fucked me in that position for 5 minutes. He fucked in his customary rythm. He switched between hard and fast and slow and deep fucks. He asked me to turn around and now he was fucking me in missionary style with my fox tail plug still inside me. I came and we kissed and he fucked me like that for ten minutes.

He stopped fucking while I lied down on one side. He slowly removed my fox tail. He bought the lube and started oiling my ass hole again. I asked him "Are you going to put it in?". He said, "Not sure if its ready yet. But lets try baby". He tried getting in and it hurt. I asked him to stop. He stopped kissed my looked into my eyes, fingered my pussy and slowly tried to enter. It hurt a little but he kept kissing and fingering. He was able to get an inch in and it hurt more. I told him I cannot take more. He asked me to suck his dick. I hesitated. He said his fantasy is to fuck all holes and end in the mouth right after anal. I gave him a blow job and he filled my mouth.

We did it again the next weekend where he was able to get in further, but he was not able to get into a rhythm as my hole was too tight and we didn't have enough time.

Source: reddit.com/r/gonewildstories/comments/33w4wh/update_my_first_wild_fuck_with_a_coworkerwith