Tom's Life Pt. 04

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Tom & Jessie go bathing suit shopping.
1.8k words
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Part 3 of the 12 part series

Updated 04/22/2024
Created 03/03/2024
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Jessie called me on Saturday when she was leaving work. She said she would be by to pick me up around 5:15. So around 4:30 I got in the shower. I knew I couldn't mess around because my parents had gone out and I could never hear the doorbell from my room.

I got out of the shower, toweled off, wrapped the towel around my waist, and headed back down the hall to my room. I entered my room and turned to close the door.

"Wow, all wrapped up in a neat little almost-naked package," came a voice from behind me that, after jumping a foot, I recognized.

"Holy SHIT Jessie you scared the shit out of me!" I said, and burst out laughing and so did she.

"What the hell are you doing here already?" I asked. "You said 5:15."

She looked amazing. Having come directly from her job in the office of a local manufacturing plant, she had on a short denim skirt and a tight-knit, low-cut top. She noticed me looking and leaned forward a little giving me a better view.

"I was going to go home and get something to eat, but then decided we could just grab something out. You can buy that too," she said with a kind of a little-girl giggle.

God, she turned me on.

She stood up and walked over to me, stuck her hand into where the towel was tucked and pulled. The towel came loose and fell to the floor. She pushed me backward until I hit the bed and fell across it.

"Let's see how big this fucker gets," she said as she took hold of my cock and started massaging it. Well, I can tell you it got hard pretty quickly.

"Not bad!" she said. "I can work with this."

She leaned down close and spit on my dick and then started stroking it. I was watching and I swear my cock was getting bigger than it ever had before.

Leaning over me she took my cock into her mouth. It was so hard it hurt. She didn't work it with her mouth though. She swirled her tongue around the shaft once or twice and then popped it out of her mouth.

She moved forward, up onto her knees on the bed straddling me. This of course caused her skirt to hike up and I could see she had no panties on!

Hiking her skirt up further, she got to my hips, reached between her legs and took hold of my dick, and guided it to her open wet pussy.

"Oh yeah. Ohhhh yeah." She started saying. "That's nice. Oh yeah, baby."

Slowly she lowered herself onto my hard shaft. I could feel the smooth walls of her pussy caressing me. And then I was all the way inside her. She just sat there for a moment, squeezing me from inside. Her eyes were half closed, her lips parted. Her tongue came out a little and she licked her lips.

"I have not been fucked in so long Tom. And you have such a beautiful hard cock. I could just sit here with you filling me all night." She said with a hint of a smile.

But then she started rocking her hips forward and back. It was a strange sensation. I could tell it was doing great things for her stimulation but only minimal for me. But it was OK because I loved watching her face.

She kept the same pace of rolling her pelvis for a few minutes, but then I could tell she was getting closer and closer because she started moving faster and jerkier. Through it all she was almost silent, with an occasional "mmmm" or a whispered "Oh yeah".

Suddenly the rocking got faster, more urgent.

"Oh yeah... Oh yeah... OH YEAH... Oh FUCK!" she yelled loudly. Again when she came, it was a flood of her hot juices. I felt it wash over my hard cock inside her and run out over my balls, across my asshole, to the bed.

After a few seconds, she stopped and sat there upright with her eyes closed. She stayed like that for a full minute at least. Then she opened her eyes, leaned down, and put her mouth on mine.

Now it should be noted here that as many times I have fucked Hal's mouth, and now his ass, my cock had never been inside a woman before. Likewise, and you will probably find this strange, I had never kissed a girl before. I must say that the last 10 minutes have given me a reason to reconsider doing ANYTHING with Hal anymore.

She kissed me several times, then straightened up, raising herself so that my dick, now soft, popped out of her pussy. Standing up, she picked up the towel from the floor, wiped herself off, and then threw it to me. She took her panties out of her purse and put them on.

"Get dressed," she said. "Let's go shopping."

That's when something occurred to me.

"Hey, how did you cum without making ME cum?" I asked incredulously.

"Just noticed that did you?" she laughed. "I have lots of fun stuff to show you darlin. Stick around. Oh and by the way..." she lifted her shirt to show me she was wearing the bathing suit top as a bra.

"I've been wearing this all day, so you know where my mind's been at. I'll be in the car. Hurry up." she said and left the room.

We drove almost twenty miles to a boutique in the next town that was like five times the size of our town.

"Oh shit she is going to nail me hard for this bathing suit," I thought. I had heard the girls in school talking about shopping in this boutique that she was taking me to, and nothing is cheap.

We walked in the door of the place and the girl there greeted her BY NAME!

"Hi, Tammy." Jessie said, "I am looking for another new bathing suit."

"OK well, we just got a bunch more in. Take your time and let me know if I can help with anything" she said, and looked me up and down. "Anything at all." She added.

Jessie walked back to the racks of bathing suits near the back of the store.

"You can sit over there. I am going to pick a few and try them on, and you can tell me which ones look the best," Jessie told me. I did as I was told and sat on the bench.

She held up one or two for my inspection or approval, but mostly she already knew what she wanted.

The shop was very slow, and Tammy was up front looking at a magazine.

Finally, Jessie had 3 or 4 suits to try on and walked toward the changing rooms. I got up and followed. As she pushed open one of the doors I quickly came up behind her, reached around, put my hand over her mouth, and pushed her into the changing room, kicking the door shut behind me.

She dropped the bathing suits on the floor and put her hands out in front of her as I pushed her to the wall opposite the door and then pressed myself against her, my hard cock against her back.

I slipped my hand around her waist while keeping my other hand over her mouth. I lifted her up and then took my hand off her mouth.

"God damn it Tom stop! I'm going to call for Tammy and she'll call the cops!" she said sounding ALMOST convincing.

I said, "Yeah if Tammy comes back here I'll fuck her too!"

I stood her up on the little bench and lifted her shirt and then her bra/bathing suit. Her fantastic tits dropped out and I started sucking them. She had her hands on the back of my head crushing my face into her tits, and I grabbed her skirt and panties and jerked them down to her ankles. She stepped out of them.

I lifted her down to the floor and turned her around facing away from me. Reaching my hands around her, I started squeezing her tits, rolling her nipples between my fingers. She shuddered and brought her hands behind her and grabbed my waist, arching her back. I squeezed her nipples harder and she cried out. Whether in pain or pleasure, I don't know but she didn't move away.

I quickly undid my pants and dropped them to the floor.

Jessie is so tiny that with both of us standing, my cock was slightly above the level of her ass. Thinking quickly I lifted her, still facing away from me, pulled her to me, and lowered her down, impaling her on my hard spear.

"Oh my GOD!!!" she said, FAR too loudly.

She brought her legs back and hooked them behind mine.

I put my hands back on her tits and squeezed them roughly. With her ankles hooked sort of behind my knees she supported her own weight and did all the work. This was a position she apparently enjoyed and I had never even heard of before.

With the mirror off to our side, I couldwatch her bounce. She was biting her lower lip and not making any noise except for an occasional whimpering moan. Her eyes were closed.

She started moving so fast on my cock I knew I wouldn't last long and neither would she.

As I watched her face, suddenly her eyes and mouth both flew open and she started making an "Ah Ah Ah Ah" sound that turned me on so much it pushed me over the edge and we came at the same time. I exploded my hot load deep inside her pussy at the same time her warm sticky cream flowed down my thighs.

"Oh FUCK TOM! Oh my GOD... God I can't stand it! Oh FUCK!" she was saying very loud.

We slowed down as our orgasms subsided. She unhooked her legs from behind mine and then she got heavy hanging on my dick.

I lifted her off and set her on the floor, she turned and sat down on the bench to catch her breath.

"Holy shit Tom. Nobody has EVER been that deep in me! Promise me we can do that again, very, very soon!" she said.

She leaned down and picked up a bathing suit.

"This is the one I want," she said. We both put our clothes back on and left the changing room.

Up at the counter, Tammy was looking at me a little differently than when we came in.

"Did you get all you needed?" she asked as I handed her my cash.

I said, "Yes I think we are both quite satisfied."

Tammy sighed, "I wish I could be that satisfied sometime."

We headed for the door, Jessie was ahead of me. As we reached the door, I turned and looked at Tammy and winked.

"See ya around Tammy," I said.

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