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Erica's Sexual Transition

Date: 10/7/2017, Categories: First Time, Author: Skinnyredles, Rating: 100, Source: xHamster

stepped into my 5 inch heels. I looked in the mirror and Damn I looked good. It was now 6PM and Mike was due to meet me. I had no idea what his plans were but told him that I wanted it to be special and that I would leave the rest to him. 20 minutes later he finally arrived. When I opened the door I was somewhat disappointed to see him wearing a polo shirt and jeans. I told him that he had to look nice. This was so far not my idea of nice. I quickly forgot about that when I saw his face. His jaw literally dropped and hit the floor. It felt like minutes that he just stood there like an idiot staring at me. Finally he stammered, “damn you are pretty.” He then took my arm and led me out the door. He wouldn’t tell me where we were going until we got there. I was seriously disappointed to see Applebee’s out the window. So far this evening was becoming a disaster. I focused on the fun that we were going to have later. After all, this night was about me losing my virginity and giving myself to him. I could not blame Mike for this because he did not know that I was going to have sex with him tonight. I ate my dinner over small talk and could not wait for it to be over. After we were done eating I told Mike that I wanted to go back to my dorm and just watch TV with him. He paid the bill, gave me a sweet kiss and e****ted me out to the car. On the drive back he placed a hand on my thigh and gently massaged it. It felt so good. When we got back to the dorm, Mike sat down on the futon ... in the room and looked for the remote. I wasted no time. I grabbed a condom that I had left in the drawer next to the door. I unstrapped my heels, walked up to him and flipped the condom to him. He looked down at it then up at me with a look of disbelief on his face. I straddled him and began to kiss him. I could feel his penis harden. He soon began to run his hands up legs and grab my ass. He squeezed my cheeks and oddly ran finger in my crack. I stopped him before he stuck it into my ass. I got off of him and took my dress off. I let his eyes wonder over my body. It was the first time that anyone had seen me with just my underwear on and in a few minutes it would be the first time anyone saw me naked. He took off his shirt and pants in record time and hopped into the bed. I got into bed with him and he pulled off boxers and laid there with his penis rock hard and his hands behind his head. I was confused. Why was he not touching me? Why was he just laying there with this dumb smile on his face and hands behind his head? Finally he asked, “aren’t you going to suck it?” I asked what it was I was going to suck. He asked me if I was going to give him head and I had no idea what that meant. I felt stupid asking. I heard of the term before but never asked what it meant. You have to keep in mind that I grew up secluded. He explained to me that it was sucking on his penis. I was totally put off by this. I told him that I did not want to put it in my mouth and he said okay. He then ...