Connie and i both enjoyed anal play and i often got to fuck her in the ass. In return, she would sometimes insert a small glass plug in my ass while giving me a blowjob. She would twist & turn it, slowly pull it almost out before pushing it back in, creating the most intense feelings.
During one of our sexy sessions, Connie was working me really good, slowly stroking my cock to full attention & occasionally tapping on the butt plug she has slid into my ass earlier. Reaching for my balls and gently tugging on them, she asked if i had ever thought about letting her peg me. Telling her that i absolutely did, i grabbed my cock from her grasp & pointed it towards her mouth, wrapping her lips around the tip, she slowly swirled her tongue around and around, making me groan with pleasure.
It was during this epic BJ i decided to let Connie into another fantasy of mine, one i had never told anyone. She moaned hard around my cock, encouraging me to continue. I began, reminding her in detail of the time we were at the pool party, where everyone got very tipsy and later, handsy with strangers under the water. It was the first time i had touched another guy & played with his cock for a bit.
Connie moaned again and swallowed more of me down her throat, i was getting so giddy with the horn i finally blurted out that, not only did i want her to peg me, i also wanted to try a real cock up my ass. On hearing this, she looked up at me, held my gaze for a second before commencing war on my painfully hard dick. Another minute and i was cumming hard, filling Connies mouth till i stopped twitching. She swallowed & licked her lips, then climbing up beside me to snuggle in.
Later, we relaxed in bed discussing my earlier confession, Connie was very keen to fulfil this fantasy for me as it had also turned her on a lot. She explained that she knew of a guy from one of her extended friend circles that would probably be up for it, and that she would make a discreet enquiry.
Fast forward two days later. Connie returned home from work & burst in to the kitchen where i was making dinner, and said that Robin, the aforementioned guy, would be up for some fun and help us out. She showed me a few pictures of the guy and he looked quite nice. He was tall with an average build, dark hair & eyes to match his olive tanned skin. Connie explained he was English/Greek & had always been gay. I decided to go for it and asked Connie to arrange something before i overthought it and backed out.
Hanging up the phone Connie informed me that Robin would be coming around tomorrow evening & to relax and leave everything to her.
The next evening around 5pm, Connie handed me some warm towels & an anal douche & advised me to go 'get ready'. I went and cleaned up for a bit, then had a long hot shower before heading off to the bedroom. Connie was waiting for me with a glass of red, and she propped me up on the edge of the bed, urging me to enjoy my wine while she gently sucked on my cock for a bit.
Connie then took my glass and motioned for me to lay face down on the bed, i duly followed orders and relaxed while listening to her move around the room. I soon felt her climb up on the bed behind me, she reached over me and tied both my hands forward around the bed frame.
I was enjoying the kinkiness of it all, when i felt a wet sensation on my bum as she poured the lube between my cheeks, then two fingers slowly began work the lube into my ass, pushing inside a little, teasing me. My cock twitched hard but i was now unable to reach for it. I felt a little more pressure on my asshole and Connie finally popped two fingers in side & worked them around, helping to stretch and relax me.
After a couple minutes of this, she withdrew her fingers & replaced them with her strap-on cock. It is one of the silicon real feel dildos, 7" long & 5" around. Another squirt lube landed on my ass, then i felt the tip of the cock being slowly pushed inside, The helmet popped inside and Connie drove forward, sliding that shaft all the way into me, filling me up. I moaned loudly as she began pulling out slowly before firmly stroking into me again and again.