Chapter 5: My date with Jessie

We met up at the Westin hotel just off I-95 at Waltham at seven on Friday 4/20.

I was so keen to show Jessie a real good time, and to demonstrate that she meant so much more to me than a quick fuck in some dirt cheap motel room, that I’d sprung some serious bucks for a high quality room in a business hotel with a nice restaurant.

The King Size bed option was enough of an incentive for me to pay the extra for the Westin. Yeah, the standard double beds elsewhere would have been okay, but a King gave me more room to chase Jessie around until she caught me. I hoped she’d see it that way too.

Despite it being Boston on a Friday, I had made good time; I was there by six twenty. I checked in and took my bag up to our room, and then went down to the lobby to wait for her. Sitting in a chair, watching all the strangers milling around, I suddenly felt at peace. At last, I was ahead of the game, not desperately trying to play catch-up. My academic workload was better than up-to-date, I wasn’t running late to meet Jessie, and I wasn’t having crazy thoughts about getting revenge on my parents for excluding me.

I suspect that I grew up a little more in that twenty-odd minutes of quiet reflection while I waited for Jessie to arrive.

You know what it’s like at the end of an important task at work? When the client has finally signed off the plans, or you’ve mailed the tender documents, or you’ve run the new sub-routine and nothing has crashed? You deserve a few minutes of quiet self-congratulation. Yeah, that kind of tranquility.

Suddenly, all those sick ideas of retribution and pain that had been running through my mind in the last few weeks seemed juvenile and utterly absurd. I knew that I didn’t want revenge pure and simple, I just wanted to fully belong to my family again. If the price of that was tolerating the injustice of being excluded, and only mildly protesting their behavior, that might well be okay.

I wondered again what would have happened if I had accepted Jessie’s suggestion to stay over with them after that first party – and with great chagrin I realized that it might well have been the best option of all, but I’d wimped out. I could have coolly sat myself down at the breakfast table, told Mom that it had been a truly awesome party and I’d have two eggs with my bacon please, and then asked Dad when he had planned to tell me – or, on the downside, I could have woken to my sister screaming rape when she’d found her brother sleeping naked next to her. It hadn’t been a choice of outcomes that had been acceptable at the time, but at least the uncertainty and feeling of rejection would have been over almost before it had begun. It would have saved me six weeks of self-doubt and loathing.

Jessie was probably my best route back to Laura, and if I got the next fifteen hours right, I could be well on my way to where I wanted to be. Even if I didn’t get the cue that I hoped to spot in time, at least I’d have had a great date with a truly awesome girl. While I was thinking of her, I saw her drive past the entrance, and I was waiting by the car park elevator when she appeared. We hugged and kissed, I took her bag, and led her up to the room.

She was impressed with the bedroom. She smirked at me as she saw the size of the bed, and she even pushed down on it to check for bounce! She took a couple of photos with her camera so she could show her roomie; I managed to keep my face out of shot. As I’d suggested, she’d brought both her bathing suit and an evening dinner dress. We washed up, she changed into her dress and applied a little make-up, I put on my coat and tie, and we went downstairs to the Relish Burger Bistro restaurant, hand in hand.

Jessie just looked so beautiful; I was aware of heads turning to admire her as we were led to our table.

Dinner was excellent.

I had a dish of braised beef short ribs with mash, and Jessie tried the seared Jonah crab cake. We shared little bites of our dish with each other, but both went for the chocolate torte dessert. We talked and laughed throughout the meal; she was amazingly good company and a great dinner companion, just like I’d hoped she would be. I happened to glance at the wall clock, and it was just gone nine! The hour and a half we’d taken to eat had flashed past.

I asked her if she wanted to go dancing or anything afterwards, but she laughed and said she was much more interested in getting back to our room. With the door safely locked and my sports coat removed, I reached into my overnight bag and pulled out the blister pack of Cialis that I had ‘liberated’ from home a fortnight earlier. I offered it to her, she grinned and took one.

“You aren’t trying to ‘cure’ me of being bisexual, are you?”

I kissed her, and looked into her eyes.

“No, Jessie, I’m not. You are what you are, and I wouldn’t ever want to change you. Yeah, I do happen to think that it would be a tragic waste of an incredible sexual being if you ever gave up on men, and I’m thrilled that you want to be with me again. I’d love it if we could keep doing this in the future, and thank you for trusting me enough to say yes to a date this time. And no, I wouldn’t want to spoil what you have with Laura, I’d like this to be in addition, if that’s okay with her.”

There were almost tears in her eyes for a moment, and then she kissed me back in a way that told me I had really gotten through to her. Then we slowly took each other’s clothes off, and I made love to Jessie for the first time.

Yeah, we made love. It was even more personal than that first time in the old family games room had been; on this occasion there was absolutely no time pressure and it was full of joy, giving and receiving. Lots of fondling, exploring, kissing, stroking, caressing, tasting.

I commented that her roomie had made a real good job of shaving her; she giggled and admitted that they’d both had a lot of fun doing it; speculating about what I might do to her had got them both hot and bothered.

Not wearing masks also made it so much more intimate than at the party; I could see the expressions on her face clearly, and we murmured endearments to each other. I’m sure that my fake Noo York accent slipped occasionally, but in the low voices we were using, it didn’t matter.

God, she was so incredibly gorgeous! I took my time kissing her from her forehead all the way down to her toes, and then half way back up again. I’d learned something about what turned her on in our previous encounters, and I made the most of that knowledge. I put my hands under her butt, lifted her up, and licked all the way from her rosebud to her clitoris. I reckoned that the gasp she gave must have used up all the air from her lungs; she started panting at that point, and her breathing didn’t slow down any for the next forty minutes. I licked her to a climax, I gave her another one caressing her G-spot with my finger, a third with a thumb on her clit and my mouth on her pussy, and then she wanted me inside her. She rode me for a bit, then we did doggie, then some reverse cowgirl, and we finished off with her legs on my shoulders as I pounded into her. She’d had an orgasm in each position, and she had a real eye-rolling doozy as I groaned my own release. We clung together; our sweat pooling on her upper chest, and then when I could operate my limbs, I rolled us both over, so that she was lying on my chest with my slightly shrunken cock still just about inside her.

She tilted her head towards me, I met her halfway and we kissed. My cock dropped out of her with the movement, and she rolled us over onto our sides so we were level and gazing into each others eyes.

“OH. MY. GOD. That was incredible, Michael, absolutely A-MAZ-ING. I’m not sure I’ve ever felt so good!”

She moved her hands up to hold my head and kissed me on the lips. There was gratitude, requited passion, friendship, affection, endorphins and something more in that kiss. At least, that’s what my brain detected.

So the words slipped out of my mouth before I could stop them.

“I love you, Jessie!”

She jumped like I had given her an electric shock, and looked closely into my face.

Fuck! FUCK! FUCK! I hadn’t meant to say that quite yet!

“Oh shit. Michael, that wasn’t just sex for you, was it?”

I had to go with the truth.

“No, Jessie, it wasn’t. I guess I’m falling for you, but I will understand if you can’t return the feeling; I know just how much your roomie means to you.”

She bit her lip in thought for a moment.

“Michael, I really like you too. I feel really conflicted over this. I’m very fond of Laura, and I hope we might be going somewhere in the long term. I get on real well with her folks, and they seem to like me. And then, I think that you’re a real nice guy too. Let’s keep it cool, and see how we go. This is our first date, after all.”

I smiled and kissed her forehead.

“Yeah, let’s keep it cool. Thank you for not shooting me down in flames. I didn’t mean to tell you quite just yet that you mean something to me, but as they say, ‘faint heart never won fair lady’. Now you know for sure that I’m going to be asking you for another date, so you’ve gotten fair warning. I WILL take ‘no’ as an answer, because I respect you, but I sure won’t be happy if that’s what you say!”

She smiled back at me. A slightly sad smile, but a smile all the same. I hoped she wasn’t just letting me down gently.

“Okay, Michael, I’ll give you a pass on that one. Don’t try and push me into a decision, though, ‘cos it might not help your case. Just enjoy what you’ve got for now.”

“I promise, Jessie. I’m not going to push you to cheat on Laura; you ain’t that type, and neither am I. I’ve never yet broken up another couple, and no matter how awesome you are, I’m not going to break that rule.”

“Thank you; I kinda guessed you were the honorable type.”

I had to ask.

“You are going to stay the rest of the night, aren’t you?”

The grin came back on to her face.

“Let me answer that with another question. Are you going to make love to me again like you just did?”

“Yes, but first of all I’m going to have another go at licking that gorgeous pussy of yours!”

Her face twitched.

“But it’s all yucky with your jizz! Don’t you want me to wash up first?”

In my enthusiasm, I’d forgotten that fact, but I threw caution to the wind.

“No! You just stay there and enjoy it.”

I tilted her onto her back and moved down her body, licking and gently biting her nipples as I passed, and got down to business. I wasn’t too squicked out at the thought of licking my own semen; Jessie (among many others, most recently Laura) had happily swallowed it and it hadn’t hurt her or them. Like most teenagers, I had once dipped a curious finger into the pool of jizz I’d just jacked onto my belly, and while it wasn’t something I desperately wanted to taste again, it was okay.

When I got down there, it was actually just fine. Jessie was a little tense to start with, presumably fearing that I’d puke all over her as soon as my tongue caught the taste, but when I settled down to licking and lapping, she got into it. Yeah, I could taste myself, but she tasted much more of her own juices, and those, I could drink all day long. It didn’t take more than a few minutes to have her squealing as she hit another climax, and then I crawled back up and kissed her neck. Her eyes were sparkling.

“No guy has ever done that for me before!”

“I’ve never wanted to do that for a girl before, either!”

She grinned and pulled me closer for a bit of tongue. She must have been able to taste herself as well as me on my lips. Then she looked me in the eye, and her whole face lit up with her smile. Hell, the whole ROOM lit up.

“Omigod! That was SO amazing. Laura’s going to be so jealous when I tell her. One of my best set of orgasms EVER, and then you cleaned me up yourself!”

She paused, her eyes a little vacant.

I worked out what she was thinking; hey, it wasn’t at all difficult to guess.

This was the opportunity I’d wargamed in my mind.

I tried not to sound as excited as I felt, kept my voice level and calm.

“Why don’t you call her and see if she wants to come over, then?”

Jessie’s face bloomed in another huge smile.

“What, right now? You don’t mind?”

“Not at all. You are even hotter when she’s around!”

That earned me another passionate kiss, then she reached over for her purse and pulled out her cell. It was answered immediately. I had guessed that they would arrange that Jessie would call Laura to confirm that she was okay, so Laura was obviously waiting for the call. It was good to see that the two of them were looking after each other.

“Hey, Roomie! What’s up?”

“Yeah, I’m missing you too.”

“Oh, A-MAZ-ING. Really great, truly incredible. SO glad I agreed to a date!”

There was the sound of an excited voice at the other end. Jessie giggled.

“Why don’t you join us then?”

I heard the squeal clearly. Jessie shook her head to clear her ear.

“Yeah, right now. Yeah, that’s it, the Westin, room 740. Oh, and there’s a pool, so bring a swim suit, and we’ll have a swim in the morning. Drive REAL carefully!”

I got us both a soda from the mini-bar as Jessie checked her phone and put it down. I told myself yet again to stay calm, and tried to stop my voice from quivering with anticipation.

Actually, I wasn’t exactly sure if it was anticipation or fear.

I’d been alone and scared for the last six weeks; I didn’t feel on my own at present with Jessie beside me, but if the next step went completely tits-up, then, man, I’d know what loneliness truly was. Whatever happened was now in the lap of the gods, or hopefully, a compassionate goddess.

Deep breath.

“She’s coming over right away?”

“Oh yeah! About forty minutes, maybe less if she doesn’t get caught speeding!”

Time to see if my plan for easing Sis into the knowledge of who ‘Michael’ really was would work.

“Cool! I’ve got an idea. Remember that game at the party when you were blindfolded and had to guess the sex of the person licking your nipples?”

“That was a whole lot of fun!”

“Why don’t you get her naked and blindfolded, and then I’ll join you? We’ll both work on her, and that should get her properly stoked before I try to fuck her brains out.”

She chuckled.

“That’s real nasty. She won’t know what’s happening or which one of us is doing it. I LOVE it!”

“So, tell me some more about your roomie. She’s a great kid, what I’ve seen of her. You two seem to get on real well.”

wo seem to get on real well.”

“Isn’t that the truth! I’m so very lucky to have met her. She’s a real friend as well as a great roomie and fuck buddy. We were put together at the start of this year and liked each other from the start. We bought some beer the first weekend and sat drinking it, and I was whining that I hadn’t gotten laid for a while. It’s not easy in our dorms; no men after ten and the workload is so intense that there’s not a lot of time for dating and finding a reliable one. Our first year both of us had made some real bad hook-ups, and it kind of puts you off. Anyway, we got to telling each other about our past experiences, and it made us both so horny that we ended up in bed together. We’d both been with girls before, so it wasn’t a problem. Fact is, it’s helped a great deal at college this year – we can take out our horniness on each other, and we don’t have to waste time finding boys, who often don’t do the job half as well. We’re getting laid most nights and have much more time for studying – it’s perfect.”

Time to steer the conversation a little closer to where I wanted it to go.

“Didn’t you say that she was the one who got you invited to the parties?”

“Yeah, when I said that I still needed some regular safe but commitment-free cock, she said that she knew a way, swore me to secrecy, and told me about the parties. The next weekend she took me home and introduced me to her parents; they asked a lot of questions but said yes, I got myself tested, and two weeks later I attended the first party.”

“And where was that? Same place?”

Jessie hesitated for a moment, collecting her thoughts.

“I’m probably going to reveal more than I should do about the parties, so you’ve got to promise to keep it a secret. I’m sure you can be trusted, as a single male you wouldn’t have been invited otherwise, but I’ve probably found out more than I should know. The parties are held at Laura’s parents house – we’ve stayed over for the weekend a couple of times when the weather was bad, so I have met them other than at a party. They’re real nice folks. You know the bedroom we were in last time when you fucked us both? It’s hers, the one she grew up in. She’s got a brother, and he’s only just gone to college, so they waited until then to host the parties themselves. Before then, they went to parties at other people’s places, but their home works so much better with the parking. No complaints from the neighbors about cars blocking the road and leaving at all hours of the night.”

Keep cool, Mike, keep real cool.

“Have you met the brother? What does he think?”

She sighed.

“That’s kind of a sore subject in the family. He’s never been told, never found out about the parties, and Laura feels real guilty about keeping it a secret from him, but her parents insist. I think she’s become more worried in the last couple of months; he seems to have changed recently and become much more distant to her. She went home at Easter and said he wasn’t his usual self at all, ignored her, dissed their parents, spent most of his time in his room and all that. She came back to college pretty upset, and I’m getting concerned about her. She’s blaming herself, and it’s not her fault. I just hope Abby and Mason change their minds. Her brother has called her several times the last ten days and been real nice to her, and she feels guilty about that too, reckons she doesn’t deserve him being friendly.”

Jessie was so concerned about her roomie that she didn’t notice that she’d given away real names. It was interesting that she was already on first name terms with my parents; there was probably a back-story there too.