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" She smiled."OK" I said. "It's time for me to get ready for my date with Chase." What are you guys doing?" Cindy said perking up."He's taking me to Seaside. Walk the boardwalk. Or something cliche likethat" That sounds romantic." Yeah, I guess it does. Sounds like something I would've done- If I was aguy that is."She laughed. "I can I help?" Absolutely" I said. I admit having a sister willing to help certainlyhelps with this transition into living as a female. And I've beenenjoying this new aspect of my relationship with her.* * *We stared at my closet for a few moments. What's a good late Septemberbeach attire?We picked out a white tank top. denim shorts, light blue sandles. I saw aflannel shirt hanging up and I pulled that off the hanger. I figured Ishould bring that too in case I get cold. I mean, it wouldn't be the 90'sif I didn't wear a flannel shirt at least once, right? After Cindy leftmy room, I went to the underwear drawer. For underwear I just went with anude bra, and pale. He then rolled Terry onto his side and lay behind him. Terry could feel the man’s cockhead against his sphincter as the Greg lined himself up. He then felt an slowly increasing pressure. After a few seconds, the pressure was great enough that the virgin’s anal ring began to give way. Terry moaned as penetration began.Greg was slow and tender about the process, massaging Terry’s chest and shoulders as he pushed deeper inside the young man. Every now and then, he’d pull back out a tiny bit, giving Terry’s anal walls a chance to relax before he began to push in. All through it, Terry breathed and moaned.Once Greg was fully inside, he flexed the muscles around his shaft, causing his erection to shift inside his partner. Terry shivered each time. Once Greg was sure Terry was relaxed, he began a slow pistoning motion. Every few strokes, he’d change his angle just a bit. Terry moaned as his insides were massaged and more fully opened in the process.After a bit, Greg hit the perfect angle.
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