Angela Plays

[Angela Plays]

Saturday’s First Date….

The three days leading up to my Saturday date with Tommy were a lot of fun in and of themselves. For starters, I saw him a couple times at the facility and was able to get my flirt game on a little bit. Everyone there, both Brent’s clients and employees know I’m super friendly and flirty, so my interaction with Tommy didn’t raise any eyebrows. (If only they knew the things I was saying, lol) We also had another brief interaction in the parking lot where I was able to get a good kiss while I pulled on his cock through his shorts. That was on Friday afternoon, and as I ended the kiss I held his cock for a moment longer, and told him not to jerk off because “I want your best tomorrow night.” As I was walking away I heard him sigh and utter “fuuuuuuuck.”
Another thing that had me so amped up during the three days leading up to Saturday was that Brent absolutely laid the wood to me good a couple of times. And while doing so he was constantly talking dirty to me about all things pertaining to my “Tommy Boy,” as he was now referred to, and how he was gonna fuck me over and over again, flooding me with his loads of cum.

Saturday finally gets there and Tommy texted asking if he was “supposed to pick me up” lol. I laughed and told him to come over at 6pm. Also told him that he could drive, but we’d be taking my Range Rover, because I wasn’t going to be arriving at a black tie event wearing a cocktail dress and stilettos after bouncing around in his jeep, lol.

Brent gave me a hug and a kiss, told me to have a good time, he would be in touch, would see me later that evening, and left the house for his event around 5:30. Tommy was right on time at 6, wearing a splendid, slim fitting suit and looked amazing. I was ready, hair and makeup, but not dressed and answered the door in a short, silk dressing robe that went barely past my ass. That in and of itself caused him pause. After catching himself he said “wow…you look amazing.” I got up on my tiptoes, gave him a quick kiss, took his hand and led him into our living room. At Brent’s suggestion, I sat him down and we had a conversation bout what the event was ….a cocktail party and social followed by an auction, for an org that supports disabled vets. We also spoke about how to respond to people asking who he was and where Brent was. I warned him that some (probably women) would make snide remarks about my date being a young guy, and that he just needed to be completely honest….that Brent had asked him for the favor of escorting me for the evening. After we finished our little talk, I gave him a good kiss, told him to relax, we’d have a great time tonight, and I went to get dressed.

Soon we were off…the event was really nice and raised a ton of money for a good cause. People were awesome, and those that I knew and did ask who Timmy was and where Brent was, didn’t bat an eye at the explanation. The only funny comment was from a much older gentleman that knows Brent well who said to Tommy “better take good care of Miss Angela tonight or Brent will rip your arms off and beat you with the bloody ends.” But then he patted Tommy on the shoulder and went about his business. (I immediately whispered in his ear telling him I couldn’t wait for him to take care of me later) This wasn’t an event that lended itself to PDA, but I did have my arm in his, and often whispered sexy things in his ear throughout the evening, and soon enough we were back in the car heading back home.

We got back to the house around 10pm and I had texted with Brent letting him know we were headed back. He told me he’d be home a little after 12, and would see me soon. Idk if it was because of trust, Tommy’s age or what, but it suddenly hit me that this was the first time that I would be with a guy for the first time, without Brent being with me. That thought hit me kinda hard and telling him I’d be right back, I left Tommy in the kitchen and went into our bedroom and called Brent. He calmed me down and told me he’d already given that some thought, and felt it was something I should experience if I was going to grow. He also said, that unless I ran him off, that Tommy would still be there when he got back home.

With my confidence restored I slipped out of my dress and into the outfit in which I would present myself to my Tommy Boy. (I posted that in the Hotties thread and will add a frontal version after I post this) I walked back into the Kitchen and stunned Tommy by my change in attire, sat straddling him in his chair, and began kissing him while grinding in to him. It was soooo different. He was shy and wasn’t sure what to do, lol. I even had to take his hands and place them on my tits, squeezing my tits with my own hands through his. I will give him credit though, he relaxed pretty quickly and the more we made out the more his hands began to explore my body. After a bit I stopped kissing him, put my forehead against his, and asked him if he’d been saving his cum for me. As soon as he said “mmmhmmm” I climbed off of him, grabbed my phone and told him told him to take a couple pics of me, which I sent to Brent. Then I took him by the hand and led him to the guest room. Once there I began undressing him and he was so nervous I swear I could feel the occasional trembling in his body. I soon had him completely undressed in front of me, and as he stepped out of his pants I pushed him back into the chair he was standing in front of and kneeled in front of him. Now….if you’ve kept up with my story, you know that between Brent and several of the men I’ve been with, that I’ve experienced some nice cocks, but I have never had one that was as hard as Tommy’s. He wasn’t the biggest (a nice 6”) but it was a steal rod and I would learn that that makes fucking a bit different too. (chalk that up to youth!) As I began to lick his shaft I asked if he’d had many blowjobs, to which he said that only one of his gf’s would do it and she wasn’t very good. That her teeth hurt, lol. I was immediately determined to change his opinions of blow jobs and took him in my mouth. I stroked his shaft, sucked on his head and felt as if I’d barely began when he said “Oh God!” His body went rigid, his hips and ass came off the chair and began shooting streams of cum in my mouth. I slurped and swallowed as best I could, but as much as I got down my throat, it was too much and soon it was running out of my mouth and onto my hand, and his cock and balls. Taking his cock out of my mouth I began ravenously licking up any of his cum I could get my mouth and tongue on. With older guys I was used to a couple good streams to squirt out and then the ooze, but even though Tommy had sent me the video , I wasn’t prepared for the real thing while having his cock in my mouth! It also didn’t hurt that his cum tasted incredible. (not to salty, lol) I knew right then that I was in trouble because how turned on his orgasm and ejaculation made me. I earlier used the word ravenous and that’s exactly how I felt. I knew it would be hard for me to get my fill of that!

That was round one and believe me when I say the night was young!

More to come soon…..

xoxo
Ang

[coastalkid]

Wow! What an experience! The being without Brent there was really awesome too in that Brent knew it would be a step in the right direction for you. Brent really masterminded the whole lead up to the sex with the escort idea. Brent knew you had to maintain your image while also knowing you'd want to tease some and couldn't resist doing it.

I'm sure that you get the irreplaceable power of youth and stamina. Age and skill can make up for a lot of things but it can't reproduce youthful performance.

[Angela Plays]

Wow! What an experience! The being without Brent there was really awesome too in that Brent knew it would be a step in the right direction for you. Brent really masterminded the whole lead up to the sex with the escort idea. Brent knew you had to maintain your image while also knowing you'd want to tease some and couldn't resist doing it.

I'm sure that you get the irreplaceable power of youth and stamina. Age and skill can make up for a lot of things but it can't reproduce youthful performance.

One thing you said there, that I didn't see at first but over time became quite evident….Brent and I entered this play as a consenting couple, finding our way, but He very quickly took control of things and is indeed the “Mastermind.” It’s strange and sometimes I still don’t know how he does it, but he always seems to know what I need or want well before I do. I think his analytical mind sees the big picture and where things are going before the rest of us mere mortals, lol.

And yes….Youth has certain aspects that no amount of experience can overcome. That doesn’t always make it better, but it is a real thing.

[hornedhubby]

You are one helleva fine writer, Ang. Vivid and passionate description.

I'm panting right now, like a hound confronting the fox.

[Scotch98]

Wow, awesome description of the blow job. I had really been looking forward to hearing about how you handled his cum and I’ll bet he will never forget that experience and you probably won’t either. An amazing piece of writing! I just love the way you describe the event and sitting on the edge of my seat to hear about the rest of the evening. Just guessing here, but I’ll bet Tommy stayed hard the entire night or close to it… I’m an old fart now but still remember my youth. Some tings are just unforgettable and you just gave Tommy one of his.

[Angela Plays]

Wow, awesome description of the blow job. I had really been looking forward to hearing about how you handled his cum and I’ll bet he will never forget that experience and you probably won’t either. An amazing piece of writing! I just love the way you describe the event and sitting on the edge of my seat to hear about the rest of the evening. Just guessing here, but I’ll bet Tommy stayed hard the entire night or close to it… I’m an old fart now but still remember my youth. Some tings are just unforgettable and you just gave Tommy one of his.

Funny that you would say that! As I finished licking up the the last of cum, that I wasn’t able to immediately swallow and spilled on him, I looked up and just smiled at him and kissed the head of his cock. At that moment he said “for as long as I live I’ll never forget this.”

[Triggershy]

Mmmm ……you are such a delight to the youth of America. These kids need a great teacher and thankfully you’ve taken on this role.

My wife and I call these WOW moments and you’ve definitely given this young man one he will never forget.

[54321]

More to come soon…..

Yes, please!

54321

[Angela Plays]

Tommy Boy continued…

After a thorough job of cleaning up the mess I’d created, I stood up and gave Tommy as kiss. He was hesitant at first so I asked him what was wrong, and he told me he’d never kissed anyone right after his cock was in their mouth, lol. It really hit me at that moment, what little experience he actually had, and that there was going to be a lot of teaching & learning moments for the both of us. I remember running my fingers through his hair, staring & smiling at him for a moment and then kissing him again. The second time it didn’t phase him and I commented that he seemed to be a fast learner. Also at that moment I realized I was about to learn something too. As I was kissing him I moved my hand down and was shocked to find that his cock had not softened.

I commented to him what a pleasant surprise that was and ask if he was ready to get in bed. He simply nodded, so I took him by the hand, let him over to the bed in our guest room and began to undress him the rest of the way. This was the first time I was able to lay my eyes on his naked body and just looking at him, seeing how toned he was, and how smooth and tight, his body was, turned me on in a way that is hard to describe. The next thing that came out of my mouth was really kind of silly when I look back on it, and always makes me laugh when I reminisce about that night. I asked him “do you like to eat pussy.” Like what 19yo hetero guy is going to say “oh god no, I hate eating pussy!” His eyes lit up like he had hit the jackpot, so I hopped up on the bed, laid back and opened my legs.

At first it definitely wasn’t the best head I’d ever received, but with a little coaching and Tommy’s desire to learn and please, it wasn’t long before he had me cumming with my hands on the back of his head pulling his face into me. I was having a blast with Tommy but with each new thing I was discovering that I was going to need to be more assertive than I had been with my past and more experienced lovers. The upside was that he super eager to please, and that was quite the rush. The thrill of this new dynamic just kept ratcheting up the excitement level inside me, and as I pulled him up to kiss me I said “Tommy, I really need you to fuck me!”

As we began kissing, I reached down, guiding his cock inside me, and just like when I had blown him, I was struck by how hard he was. He wasted little time, began to really pound me hard, and another orgasm slipped up on me. As my pussy locked down on his cock he began to groan and unloaded again, but this time in my pussy. He lasted longer this time than he had in my mouth, but the sex had only gone on for 2-3 minutes before we had both cum. I kissed him and as he rolled off he said “I’m sorry I came so fast, but I couldn’t help it.” I heard what he said, but was really focused on feeling the amount of cum leaking out of me and running between my ass cheeks when he pulled out, lol.

I curled up next to him with his arm around me and told him never to apologize for being so turned on that he came fast, and that for me it was the ultimate compliment, and made me feel really good that he was so into fucking me. We laid there and talked for about 10-15 minutes, with my hand rubbing his cock and balls, and while he did soften up more than he had after the blow job, he never went completely flaccid. I looked up at him, laughed and said “my god…does your cock stay hard all the time?” He blushed and grinned a little, and I began putting a little more urgency to the hand job I was giving. With him being fully at attention again, I climbed on top of him and lowered myself down on his cock. I remember saying to him “this time I’ll do the work and we’ll see if we can make it last a little longer.” And we did! This time we fucked for 20-30 minutes. I had several orgasms, but each time he got close I would stop moving and just sit there on his cock until the urge to blow subsided. At one point he said “you’re fucking killing me!” My response was simply “I think you’ll survive.” I finally asked if he wanted to cum and when he said yes, I slid off his cock and began stroking and sucking him. Not because I didn’t want his load in my pussy, but because selfishly, I wanted to watch him ejaculate. I wanted to SEE what I had felt in my mouth and pussy, and I wasn’t disappointed. Sitting on his legs when he came, I watched as the first stream went up and landed on his chest and neck and the second on his stomach. There wasn’t the volume of his first two loads but it was still incredible to see the cum exploding out of his beautiful cock, and I made sure none of it went to waste. Of additional consequence, this time he wasn’t hesitant at all when I kissed him after lapping up his cum. Although he was taken aback a little when I transferred a bit of his cum back to him, lol.

Another thing I’d soon discover about a guy Tommy’s age was that when they fall asleep they are dead to the world, lol. Around 1am I felt a hand moving my hair and when I opened my eyes, I see Brent kneeling beside the bed smiling at me. He motioned for me to come with, so I eased out of bed and followed him into the kitchen. I think I could have jumped up and down on the bed and poor Tommy would have slept through it though, lol. I gave Brent the condensed version of how things had gone, and told him it was a lot of fun. He asked me if I was done with Tommy for the night and if I wanted to come to bed (our bed). I was really just being a smartass, and said “hmmm….thats a tough decision.” Well that flipped a switch in Brent. He took hold of my hair and said “on your knees, and take my cock out.” So there I am….in the kitchen, naked and on my knees, my husbands pants around his ankles, and his cock in my mouth. All with my Tommy Boy crashed out in a room 10 steps away! Then, Brent asked me if I wanted to suck Tommy again. All I could do was nod so he pulled his cock out of my mouth and stood me up. He undressed the rest of the way and motioned to head back into the guest room. Taking me to Tommy’s side of the bed, he stood behind me and pushed his cock inside me, leaned forward and whispered “now suck his cock.” as he began to slowly fuck me. So I pulled back the bed covers and began to work on Tommy’s cock. Well let’s just say when Tommy awoke that he wasn’t prepared for what was taking place. His eyes got wide, but to his credit, he didn’t freak out. He did have another quick orgasm though, and after swallowing his load, I laid across his body and he got to watch, up close, Brent reclaim his wife’s pussy. After cumming in me, and me returning to my knees to clean him, we left Tommy alone in the guest room, told him to get some sleep, and we’d see him for breakfast in a few hours. We showered together, I snuggled up close to my man, and slept like a baby. It wasn’t the best first time sex with a man I’d ever had but it was definitely different and enjoyable.

It was a fun and educational, first time with Tommy. A nice beginning for sure. My time with him lasted through the Spring of 2023 and next post
I’ll share a couple of other memorable experiences we had together!

xoxo
Ang

[Tryn]

Another fantastic replay of your hot past! Thank you!

[Angela Plays]

Thank you!

[pixmangurn]

Angela, your writing is so compelling, descriptive and erotic! Thank you for sharing your journey in words and pictures with us!

[coastalkid]

I have a feeling that your parting with Tommy was VASTLY different than your parting with Nick.

[UKDan]

Thanks for another in depth retelling, very erotic

[Angela Plays]

I have a feeling that your parting with Tommy was VASTLY different than your parting with Nick.

As usual…The Kid is spot on with his assessment. Tommy moved a fair distance away from us to finish his college studies and athletic career. (He’s a junior in college now) His folks still live here locally, and is in town occasionally throughout the year, mainly holidays. I’ll share this here now….he and Brent have become very close. He credits Brent with turning his playing career around with the improvements he made to his physical conditioning. Also, Tommy doesn’t have a great relationship with his dad and Brent has become a real mentor to him. He often has said that Brent and I turned him into a man. (Although I’d say Brent and I went about it in different ways, lol) Tommy still calls Brent almost weekly and they text even more regularly than that about all matters of life. Me on the other hand…We were exclusive from February through June of 2023, and have had a few romps the last couple of years when he’s been home visiting his folks. He’s only one of two men I’ve been with again after a time exclusive play has ended, and it’s been pretty fucking amazing to witness his maturation as a man and a lover. We haven't seen him and I haven’t been with him since August. He also has a serious gf now, that he happens to be bringing home with him at Christmas, so who knows if I’ll ever be with him again. If that ends up being the case I’m totally fine with it, but I have a feeling that in some fashion Tommy will be part of our family for the long haul.

[coastalkid]

I have a feeling that Brent saw something good in Tommy from the "get go". Tommy is a young kid, dedicated to his sport, and wants to aspire to his highest potential, Brent probably admired that about him. I would guess that being in the "training" business, Brent would have a lot of experience with recognizing motivation(s) and personal behaviors. He trusted his assessment of Tommy. It made things easier for him to do what he does, encourage, influence and gently nudge to achieve the results he wants.

After your very first talk with Brent when you were just considering Tommy it made things click in Brent's head. After the Nick episode Tommy represented a totally different scenario. This idea was much more in his comfort zone. He had close contact with Tommy and he knew that you knew he did too. The difference in age was significant too. Brent also knew that Tommy was a young kid and he'd eventually move on and live his life.

Knowing what I think I know of Brent, does he ever make a comment after talking with Tommy on the phone now just to see if he can get a reaction out of you just for fun?

[jane]

the younger men definitely do tend to ejactulate more semen

[Angela Plays]

the younger men definitely do tend to ejactulate more semen

Mmmmm Hmmmmm

[Angela Plays]

I have a feeling that Brent saw something good in Tommy from the "get go". Tommy is a young kid, dedicated to his sport, and wants to aspire to his highest potential, Brent probably admired that about him. I would guess that being in the "training" business, Brent would have a lot of experience with recognizing motivation(s) and personal behaviors. He trusted his assessment of Tommy. It made things easier for him to do what he does, encourage, influence and gently nudge to achieve the results he wants.

After your very first talk with Brent when you were just considering Tommy it made things click in Brent's head. After the Nick episode Tommy represented a totally different scenario. This idea was much more in his comfort zone. He had close contact with Tommy and he knew that you knew he did too. The difference in age was significant too. Brent also knew that Tommy was a young kid and he'd eventually move on and live his life.

Knowing what I think I know of Brent, does he ever make a comment after talking with Tommy on the phone now just to see if he can get a reaction out of you just for fun?

As I’ve said before…there’s a lot of good nature ribbing in our home. Those that are thinned skinned wouldn’t fair well, so yes….example.

Last week we’re were sitting around watching tv and Brent goes…”oh, forgot to tell you that your Tommy Boy called today.” My response…”oh he’s all man now.” Brent’s comeback…”stop acting like such a horny slut.” My comeback…”it’s your fault I ended up this way.” His response…”whatever, you win.” My response (because I must have the last word)…”I thought so.”

[superb101]

Hopefully, you get to see Tommy again soon

[magnus]

The adventures of "Tommy Boy" are off-the-charts hot and Tommy sure got to live every young man's dream. What a wonderful gift for a young man to have an experienced, confident and beautiful woman to guide him through some incredible sexual experiences.

My guess is he will find a way back to your bed at some point.

[hornedhubby]

Wonderful, heartwarming and very sexy story.

I played a lot of tennis in HS/college, too. Also had a special fling with an older woman toward the end of that era. She was incredible in bed, but she was an even finer friend and bartending teammate. From both angles she really helped me finish growing up. So this story was like revisiting a precious memory.

Thank you, Ang.

Happy holidays to you and Brent and thanks for sharing.

[pixmangurn]

” My comeback…”it’s your fault I ended up this way.” His response…”whatever, you win.” My response (because I must have the last word)…”I thought so.”

Well played Angela, well played.

[Triggershy]

Wait Tommy plays a sport……I lost focus after the cougar swallowed his cum and then fucked him soooo good.

[Angela Plays]

Wonderful, heartwarming and very sexy story.

I played a lot of tennis in HS/college, too. Also had a special fling with an older woman toward the end of that era. She was incredible in bed, but she was an even finer friend and bartending teammate. From both angles she really helped me finish growing up. So this story was like revisiting a precious memory.

Thank you, Ang.

Happy holidays to you and Brent and thanks for sharing.

You’re very sweet…thank you!