S002: Scott’s Chronicle: Brunch

It took a lot for you to fall asleep that night. Even wearing panties for the night, which usually helps you to relax and fall asleep didn’t help. Tonight, meeting Becky, your mind is racing.
Am I really offering you what you think I am? Would I really do this with you? But to what degree? Are you really ready to go so much farther than what you have already?
You have read a lot about this fetish online. You know you are not transgender or even a transvestite. You want to play, and feel like you are a girly girl, but you don’t want to transition to being one. No, it is all just a sexual arousal thing, thinking about being dressed and acting like a girl. And someone treating you like one.
In my car, when I called your glans you “clitty” really stirred something in you. We both knew it wasn’t, but playing that it was added to your sexual experience. And that probably contributed a lot your cumming so quickly.
But sleep you do. You are up at seven a.m. though and hurry to get nine holes of golf in to relieve some of the building up pressure that the thought of noon brings to you. You do play the course quickly, and not your best score, but it has limbered you up some.
Back home you shower and then put on your pretty new panties you had just bought a week ago. You were saving them for something special, and our brunch and what might follow with Becky soo qualifies as that.
You are on pins and needles as you wait for noon to arrive. Finally, it is five to; you leave your house and walk the block to my condo. As you feel the silk of the panties rubbing against your ass cheeks and cock it is so enjoyable. Perhaps your next round of golf you should wear panties. The feel of them brushing against you as you lift your arms to swing. But that is for another time. Now you are at my door and pressing my bell.
You can hear me approaching the door, and you feel yourself harden a little in anticipation.
I open the door and invite you in. Seeing me now in daylight I look lovely to you. You pull me to you and kiss me long and deep. You feel the urge to do this right away, to see if I return your kiss. Oh yes, I do. We stand there kissing like we had started in the parking lot last night. It is almost like a continuation of that dance we began then.
We finally break apart to catch our breaths, and I take your hand and lead you to the kitchen. There are plates of eggs, bacon, and toast on the table along with glasses of juice. We sit down and begin to eat. As we do, I tell you what I thought we could do today, if you want to.
“Scott, do you really want to pursue this side of you more? Go the full way to being crossed dress and play at being my special girlfriend?”
“Becky, it is something I have longed for since I first found how much I love wearing panties. I was so afraid of anyone finding out about this side of me I kept it so private and to myself. No one knows this facet of me, and I never want it to be known.”
“Oh Scott, I understand that completely, and it is the same for me. I think I would enjoy playing with you immensely, but no one must ever know about this side of us together.”
It is music to your ears. Someone so willing to explore this with you, with total discretion on both parts. You find yourself getting very hard as we eat and talk.
I ask if you would like to go shopping after we eat to get you some makeup, dresses, and nighties. And more undies and such if you need more of them.
This is too much; you are so hard now. The thought of shopping, with someone, for those things for you overwhelms you. All you can do is nod your head to me.
I see how red your face and neck are getting, and glance down at your crotch. “Well perhaps shopping needs to wait for a little while,” I smile at you, take your hand again and lead you to my bedroom.
There I undo your pants and let them fall to the floor, then lift your shirt off. You stand before me in your matching bra and panties set. I lift my dress over my head, and I too stand before you in just bra and panties. Not as fancy as yours though.
You press yourself to me and help me drop back on the bed as you kiss and hug me. You are lying on top of me, our panties crushing against each other, our sex both throbbing right now. Something about feeling each other through our panties, you being so hard, me dripping juices saturating the crotch of mine was more arousing than if you would have just thrust into me.
We stay that way, rubbing against each other as our hands find their way to each other’s cheeks and squeeze and press each other closer together. Deep kisses and licking on each other’s necks and ears add to the play.
I am excited to see, that while not very big, you do have small man boobs, just a little jetting out, your nipples peeking over the top of your bras. I lean and take one in my mouth and suck on it, making you moan with pleasure.
My hand now reaches down and rubs the glans of your cock through your panties. You are so hard now. I whisper in your ear, “Sweetie your clit is getting so hard and solid now.”
This almost takes you over the top again, but you control yourself, because this time, you do want to be inside me. Your fingers are playing with my slit, slipping in my vag and rubbing my clit, feel me throb and clutch against your fingers when you are in me. This and my wetness tells you I am ready. You put your hands under me and lower my panties over my cheeks, your fingers rubbing me as you do, down my thighs, over my knees, and slowly finish pulling them off my calves.
I lay there staring in your eyes, open and ready for you. Only my bra is on. And you get to that same point as you pull your panties off and climb between my spread legs. As you thrust yourself in me, you lean on me, so our bras do rub together as we begin the ride.
You press so up in me as I moan with delight — you back out some and then a second, third, and more thrusts over and over. The walls of my vag do clutch and hold you on each thrust. My soft, warm, and wet vag is a longed-for present for you. It has been a good while since you have been in such a place. And with me now grabbing and squeezing your tits through your bra brings home to you how this is a much more unique ride than you have ever been on before.
I moan and arch my back a couple of times as you thrust in and out. Oh, you are so close to cumming now. You feel the throbbing in your cock telling it will be very soon. You moan deeply and spurt your whole load into me.
You collapse on me as you feel me tighten over your cock over and over. Finally, draining the last juices from you I relax, and you lift and roll off me. Taking me in your arms we both lie there trying to catch our breath.
“Well, I guess shopping will have to wait for a bit,” I tell you as I lean and kiss you, then lay my head on your shoulder.
And laying like this we both fall asleep. Neither of us had gotten that much sleep last night, and the feel of being this close, in each other’s arms, just lulled us to slumber.