A couple days later, I’m very happy to see Emily wearing very cute silver cotton dress that I’m quite fond of. The dress is pretty loose and flowy and about knee length, but my favorite part about this dress is the neckline. The top had thin spaghetti straps and while the neckline wasn’t low cut in the sense that it plunged deep between her boobs, it was cut very close to where the top of her bra would be. She would only ever wear this dress with a particular silver Victoria’s Secret bra. If you asked her she would say it was so the straps would match and not look too trashy. However, through our time dating I knew that this dress needed constant adjusting to keep her bra cups from peeking out, and that was the real reason she would only wear that matching bra with this dress.
We decided to watch a TV show together in her room and I was happy to see that she kept the silver dress on. We were both seated with our back against the headboard of the bed and our legs stretched out in front of us. This wasn’t the best position for a view but there wasn’t much I could do about it given that we were watching the TV.
During the commercials we would chat about our day and make other small talk about this and that. During one particular break, we somehow got on the topic of tickling and jokingly made a move towards each other’s sides to try to tickle the other one. We both had a competitive side, and neither of us wanted to be outdone, so one tickle soon turned into a full on wrestling match to pin and tickle each other. I let Emily believe she had a chance and would let her come close to gaining an advantage, but eventually I used my size and strength to get on top of her and pin her down. We ended up kind of sideways across the bed, Emily on her back with me on top of her pinning her down, and as I dug into her side to give the final tickle and declare my victory, Emily tried to wiggle away and ended up with her torso hanging off the edge of the bed.
I reached down and grabbed Emily by both wrists to pull her back onto the bed and asked if she gave up. As I pulled her back up I noticed a good portion of both bra cups peeking out from her dress, so when she said she did not give up, I gave her a push back off the side of the bed and tickled her some more resulting in more squirming. Again I stopped, grabbed both wrists and pulled Emily up to a sort of sitting position to ask again if she gave up. This time I noticed her dark areolas were visible above her bra, so when she again said no, I pushed her back over the edge of the bed and resumed tickling.
Wanting to move things along, I was really tickling her hard, causing a lot of squirming from Emily. All of our wrestling had caused her dress to slip up a little bit, but I had yet to see what panties she was wearing, so I used my intensified tickling as a cover to slowly hike her dress up more until I could see her bright red nylon panties between my legs. I left her dress hiked up with her pubic mound visible as I once again reached down to pull Emily back up. I couldn’t get her back up fast enough expecting a great view, and was happily rewarded when I could see both of her nipples sticking out above her silver bra and dress.
I couldn’t take my eyes off of her exposed breasts. It had been months since we had dated and I had seen her like this. She was a petite girl, but had full C cup tits, and they looked wonderful poking out of her dress. I quickly achieved rock hard status as I continued to look at her boobs and it wasn’t long before my uninterrupted staring caused her to look down and notice her exposure. Emily let out a squeal, but hesitated just a moment to let me take in one last second of her exposed breast before pulling her top back up and laughing about the incident. As Emily was laughing about what had just happened, she looked down and said something to the effect of “Not my panties too.”
This drew my attention back down to her exposed lower half between my legs as I straddled her hips. Emily tried to pull her dress back down but was having difficulty with my legs on either side of her hips. I decided to playfully fight back, pushing her hands away and joking that “I liked the view” and “they were cute panties.” As I pushed her hands away, Emily kept fighting her way back to her dress in an attempt to pull it back down. The whole time, her arms and hands are brushing up against and bouncing off my clearly engorged cock through my shorts. Emily pretended not to notice and to only be concerned with pulling her skirt down, but there was no way she couldn’t feel it. Our wrestling began to intensify, and any progress Emily made was quickly lost to our squirming around on the bed. As I gained control of both her wrists, I pushed her back off the edge of the bed again and began to shake her up and down similar to the dunking motion of a tea bag.
There was no hiding it now; I was clearly trying to get her tits to pop out again, but since I had a firm grip on both of her wrists, there wasn’t anything Emily could do about it. It was pretty clear that while she put on the façade of caring that I could see her exposed, deep down she didn’t really mind as she began to laugh and joked that she was going to fall out of her dress again. I pulled her back up, and sure enough, both breasts were once again exposed in all their perky glory. This time however, I didn’t let go of her wrists and enjoyed the view for a moment before leaning down and wrapped my lips around Emily’s nipple.
As I did this, Emily let out a huge sigh of pleasure and I knew things were going my way tonight. I let go of her wrists to slip her dress and bra straps off her shoulders and release her large sized breasts completely. No sooner had I let go of her wrists, Emily’s hands made a straight shot for my crotch and began to rub my cock through my shorts. Emily slowly ran her hand up and down the length of my cock as I circled and teased her nipples with my tongue.
It wasn’t long before I could feel Emily begin to fumble with my belt. I reluctantly removed myself from her nipple and stood up next to the bed to undress myself. I removed my short exposing my cock standing at full mast and then pulled my shirt up over my head and tossed it aside. When I went to rejoin Emily on the bed, I was pleased to see her gaze fixed on my fully erect cock.
I climbed back onto the bed and grabbed hold of Emily to swing her round so that she was laying the correct way on the bed. Given her petite frame this was pretty easy and I knew it turned her on to be handled like that. I then lowered myself onto her and locked my lips with hers. As we made out, I began to slowly grind against Emily’s crotch, enjoying the feeling of my cock against her nylon panties. As nice as that feeling was, all of the buildup over the past couple months made me want to get down to business. I lifted myself off of her and into a position to pull her panties down and threw them aside before resuming my position on top of her. Again, I slowly began to grind against her crotch, this time enjoying the sensation of her wetness on my cock. I reached down between us and positioned my cock at her entrance and slowly slid the length into her.
It took quite a bit of willpower not to blow my load on the first stroke as Emily’s incredible tightness hugged every contour of my cock. I began to slide out and then back in again as I picked up a (very slow) rhythm. Emily was moan with each thrust, thoroughly enjoying what I guessed by her tightness to be her first action since we stopped dating. I hadn’t gotten much action either aside from all my spank bank session fueled by encounters with Emily over the past few months and it wasn’t long before I felt myself getting ready to climax.
Not wanting our session to end too quickly, I rolled over onto the bed and told Emily to ride me. She quickly obliged, hopping on top of me and impaling herself on my cock. I knew with her on top I’d last longer so I was able to pick up the pace with her and meet her thrust, reaching as deep into her as I could. Being on the bottom also afforded me the view of Emily’s large breast, free of her dress and bra and bouncing vigorously as she rode me. I reached up and grabbed her breasts, pinching each nipple and eliciting a scream from Emily. Her breathing became short and rapid and I knew she was about to cum. She picked up her pace, and I increased my intensity in meeting her thrusts.
Her small frame and light weight allowed me to get some distance off the bed as I thrusted upwards in time with her. As her individual moans turned into one continuous moan and her orgasm swept over her body, I gave one last powerful upwards thrust, this time lifting Emily’s knees off the bed, causing her to literally ride me. As I did this she screamed as a second orgasm coursed through her body.
Now it was my turn. I rolled Emily off of me and onto her back on the bed and arranged her legs so that when I leaned forward to enter her, they would be on my shoulders and she would be virtually folded in half beneath me. I wrapped my arms around her thighs, lifted her hips off the bed and easily slipped back inside of her. I wasted no time and began thrusting hard and fast, slapping against her with each thrust. Within seconds I was ready to go and gave a couple more thrust before burying my cock as deep inside of her as I could and letting my orgasm take over.
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