**Once Upon a Life**
**Part 2 of Many – Matt’s first night sleeping all night with a female.**
Here is the story of how Matt spent his first ever night with a female, a young lady.
Near the end of the summer there was an end of season picnic and awards ceremony for a summer league baseball program Matt had played in.
The season was over and all of the families and players were invited to a huge park. It was a huge pot luck, many grills were going and people were playing catch, Frisbee etc.
During the time there in the park, another ballplayer that Matt knew came up to talk to him. Matt knew of this guy and had known of him for years and years as they’d played against each other many times. But, this guy went to a different high school than Matt did, in the next town over so while he knew of him, he didn’t really know him. They didn’t hang out together off of the ballfields etc.
This guy’s name was Wes. Wes came up to Matt to talk to him and he invited him to go on vacation with his family and him in like a week. They were going to drive hundreds of miles away, many states away to spend a week in a rental house on a lake. His family had a speedboat that they were going to tow so they’d be able to water ski, go tubing etc.
It sounded great to Matt for many reasons but again, Matt didn’t really know this guy, Wes, he only knew of him. But, the number 1 reason it sounded great to Matt was that Wes’s older sister Tami was beyond gorgeous.
All the ballplayers knew of Tami. She was beautiful, blonde, slender and busty. They’d known of her for years as she went to some of the games with her parent’s to watch Wes play, not all of them, but some.
Matt just loved the thought of seeing Tami in a bathing suit, water skiing etc. Honestly, she looked like she walked out of the pages of Playboy.
As Wes and Matt were talking, things got much more interesting, in a HURRY. Wes was honest with Matt and both he and Matt knew that they didn’t really know each other, hadn’t hung out before etc.
Wes and Tami’s parents had always let each of them invite a friend to go along with them on their family vacations each summer. They’d done that for many years. Being that Tami and Wes weren’t young children anymore, they began to change things up.
Tami would tell Wes what guy to choose and bring on their family vacation and Wes would tell his sister Tami which girl to choose to bring on vacation.
Wes told Matt that his sister Tami had just told him to ask Matt to go on their vacation with them. Wes told Matt that his sister thought he was cute. Matt was going nuts inside as Tami looked like she had just walked out of a Playboy Centerfold and on top of that, Matt had just gone to the park for end of season awards and picnic. When he went to the park that day, he had no idea that he’d be invited to go on another players family vacation with them and that it was his beyond gorgeous sister who wanted him to go and not Wes himself.
Matt went over to his parent’s and they were OK with it, they just wanted to meet and talk with Wes’s parent’s, which they did as they were all there at the park, the picnic.
The vacation was in like a week as the summer was coming to a close, the summer league baseball season was over, hence the end of the season awards ceremony and picnic.
Being that it was the early 1980’s, the scene as they took off on their journey resembled an early Chevy Chase Vacation movie. Wes’s parent’s had one of those huge old station wagon’s (again, early 1980’s) and they were towing their speed boat on a trailer behind them.
Tami brought a girlfriend named Lynette (for Wes) and of course Matt was along with Wes for Tami.
They were listening to newly released music from Prince like Little Red Corvette on the trip down.
It was a long trip and towing the boat made it take longer. Matt wasn’t aware of the itinerary at all. Wes’s parent’s stopped for the night in Nashville as they weren’t close to their final destination. Matt had no idea they were going to stop anywhere as Wes’s parents hadn’t discussed that. Matt assumed they would be driving straight through.
Matt’s next surprise was that instead of Wes and Matt sharing a hotel room, Tami and Lynette sharing a hotel room and Wes’s parent’s in another room, all 4 of them were to share the same hotel room.
Again, none of this had been discussed or shared with Matt ahead of time but he wasn’t complaining at all. In Matt’s mind, he and Wes would share one of the two double beds and Tami and Lynette would share the other one.
After dinner and then going to their rooms, it became time to go to bed. Matt came out of the bathroom in their hotel room and he saw Lynette in one bed and then he saw Wes get in bed with her, next to Lynette. Again, NONE of this had been talked about with Matt. It was a complete surprise to Matt.
Tami was only wearing underwear and a big soft, worn out oversized t-shirt. Matt was in Heaven and Tami told Matt to help her turn back the sheets of their bed. Matt was beside himself. He floated to the opposite of the bed and he and Tami were facing each other across the bed from each other as she was going to turn back the sheets. When she leaned forward, over a bit, Matt could see her breasts as she had no bra on for the night and her t-shirt was oversized and loose.
He’d known of Tami for years and years but never in his wildest dreams did he think something like this could happen. They lived in a town over from the town Matt lived in, they went to different high schools etc.
Matt had never slept in the same bed all night with a lady before.
When Tami and Matt turned back the sheets, he jumped into the bed quickly because he was becoming erect due to having seen Tami’s boobs when she leaned over to turn back the sheets with him.
Tami told Matt to move over by her. He wasn’t taking the lead, he’d been shocked to even have Wes ask him to go on their family vacation. Then he was shocked when Wes told him that Tami thought he was cute and that she told Wes to ask him to go on their family vacation with them. Matt hadn’t known they were going to stop and spend the night along the way. Then, when they stopped Matt had no idea that all 4 of them (Tami, Lynette, Wes and Matt) would be in the same hotel room and he certainly had no idea that Tami and him would be sharing the same bed all night.
Matt slide over next to and along Tami and she felt Matt’s erection against her body. Tami moved her arm to place her hand on, over Matt’s erection. She moved her hand up and down along Matt’s shaft and then she squeezed it a bit. After doing that, Tami got out of the bed and walked over and around the other bed to whisper to Lynette.
Matt didn’t know what she was saying to Lynette but moments after that, Lynette and Wes were getting out of bed and they were going to go out of the room and take a 30 minute walk.
Tami walked behind them to the door and when they had gone out, she locked the door behind them and as she was walking back to the bed Matt was lying in she was taking off her nightshirt and Matt stared in awe at her chest. She was standing right next to the bed when she leaned over a bit and took her underwear off. Matt’s heart was racing and there was no mistaking what was going to happen next.
Matt had just won the all-time best lottery ever. Tami was a guy’s dream, at least physically. Tami just got on top of Matt, straddled him and she began to take his cock out of his boxers and she played with it for a bit in her hands and then she gave him a partial blowjob, just playing with it in her mouth for a bit.
Matt wasn’t really thinking anything right then to be honest. I mean how could he? Tami was just lubing Matt up with her mouth, her saliva was all but Matt didn’t know that, wasn’t thinking about that as she was naked, she was straddling him, she was touching and playing with his cock and did I mention she was naked? And gorgeous? And busty?
Tami slowly lowered herself down onto Matt’s erection, little by little. She stopped for a bit to let herself adjust and then she lowered herself down a bit more. After several minutes she laid her chest down onto Matt’s face for a bit and then she raised up a bit and kissed him slowly, for a while.
Tami then pushed her torso up with her arms, her hands were on each side of Matt’s upper chest, near his shoulders when she pushed herself up a bit. She didn’t raise all the way up to a 90 degree angle on Matt. She only rose up like 45 degrees and then she began to move her hips so she was moving up and down on part of Matt’s shaft.
Matt was lying there flat on his back looking up at one of the most beautiful young ladies he’d ever seen. Her boobs were moving and swaying around and it was hypnotizing to Matt. At one point Tami took one of Matt’s hands and placed it on one of her breasts and told him to hold them, play with them and to not let them bounce all over so Matt followed her lead and began to touch and lightly squeeze her amazing boobs. Matt didn’t think much and he began to lick and suck Tami’s breasts while she was riding him and while he was caressing her boobs with his hands.
Those 30 minutes were over far too soon but then Matt realized that he was going to be sleeping next to, against, pressed up next to this lovely creature all night and he was happy all over again.
Lynette and Wes returned and they were knocking lightly on the door. Tami told Matt to go let them in as she was laying comfortably in the bed and Matt wasn’t going to argue with her about anything so he got up to let Lynette and Wes back into the room.
Matt only got to have sex with Tami one more time that week but it came with another huge surprise for Matt. Matt was napping in a bedroom and he was awakened by hearing Lynette and Tami talking to each other while standing next to the bed that Matt was sleeping on. Before Matt opened his eyes, he could hear the two of them talking and they thought he was still sleeping. They were talking about his muscles, even when he was sleeping.
When Matt woke up, he found out that Wes and his parent’s had left to go grocery shopping so only Lynette, Tami and Matt were there. The three of them had sex together. Again, that wasn’t something that hadn’t been talked about or told to Matt.
Lynette was pretty, but nothing like Tami. Lynette was brunette and Tami was blonde. Lynette was tall, skinny and flat chested. Matt loved brunettes and it was amazing seeing a blonde and a brunette, a busty and a slender girl both at once. The views and the sensations were out of the world for Matt when having sex with those two.
Lynette had heard from Tami about Matt’s cock and she was happy to see it, touch it, and play with it and to have it. Matt was in Heaven again. In most respects they were using him but it’s not like Matt was thinking about that at all. Matt had no complaints, then or now many decades later.
That was the first time that Matt was able to experience two ladies mouths and tongues on his cock at the same time and well, firsts always stick out in one’s mind.
That is the story of how Matt was able to spend the night with a lady for the first time ever in his life and he had no idea it was going to happen until literally moments before it did. When Matt had gone into the bathroom in their hotel room to change, to brush his teeth etc. he assumed that when he came out he’d be sharing a bed with Wes but he soon found out he was going to get lucky in more ways than one.
**End Part 2**
Part 3 will be about Matt’s 1st night with Julianna & how Matt met Stephanie.
Source: reddit.com/r/gonewildstories/comments/a76pf9/once_upon_a_life_part_2_of_many_mf_matts_first