The Office Boy Ch. 06

"Before you go Glenn there is one last thing I would like to do for you. Have you ever had anal sex before?" I must have looked alarmed. "Don't panic I mean my anus, for the moment anyway." I smiled and nodded. "Okay, lets get dry and go in the bedroom again."

Having dried ourselves we sat on the bed. "Now Glenn, I have done this lots of times but please follow my lead or do what I say, understand?" I nodded. She lay face down on the bed, "Now gently rub my shoulders and give me a massage as even I have to be relaxed in order for this to be nice for both of us. Trust me you will love this." I rubbed the massage oil into her shoulders and back. Ruth closed her eyes while I kneaded and rubbed her skin. After a while she opened her eyes, "that's really good now I think I am ready. Take the lubricant you used earlier and liberally apply it to your erection. You done it?"

"Yes." I replied breathlessly. "Are you sure you want me to do this?"

"Of course Glenn. Now...that's it gentle at first." I placed the head of my penis against her arse and pushed slightly. "A little more pressure, yes that's it." Her hole yielded and I felt my lubed head open her muscles as I entered her bum. "Keep going." She urged, as I gently pushed deeper and deeper. "Now I will tighten for you, don't move." I stayed buried inside her as she flexed her muscles, which tightened around me. "You can fuck me now but keep the penetrations straight and try and keep a constant rhythm. It feels really good Glenn. You are just the right size for this neither too small nor too big. In fact I would say you are perfect."

"This feels so good Ruth. I don't know how long I can hold on for though."

"It's ok, just keep the movements steady and smooth. I'm going to rub my clit and believe me I won't take long. Also I don't think you will be able to stand it when I cum trust me I will milk you don't worry." I carried on fucking her slowly and steadily holding my orgasm as best I could. Her arsehole was so tight but I wanted her to climax and feel what she had described. After a few moments Ruth spoke "I am about to cum, just stop in me as deep as you are now and don't move. Trust me."

She continued to masturbate her clit when she let out a low moan and braced herself. I have never felt a sensation like it as she came her arse contracted really hard on me and although we weren't moving it felt like fingers rubbing my cock. I slowly moved back and as I did so felt the unmistakable feeling of my cock releasing as I came inside her back passage.

"Did you enjoy that?" She asked me breathlessly.

"It was like nothing I have ever felt before."

"Okay, we really need to get cleaned up now. You realise you have cum in my mouth, cunt and arse today?" She winked then kissed me again. "You are a lovely lad some woman will be very lucky to catch you."