How long is an "overnight" session and what happens--just one time?

[Yankee]

Can guys tell me how long an overnight session would be, and what time in the morning am I expected to leave my escort's hotel room by? I've never had sex with a guy, but I did make out with an escort for an hour for the first time earlier this month. Found another escort with great reviews and I want to lose my virginity with him but i'd rather the first time be with a guy I spend the whole night with-- as I'm guessing it will hurt the first time and be a little easier a few hours later--like at 4am. How long does an overnight last? Is it okay for me to expect or ask to get nailed twice during an overnight session? I'd stay in the room the whole time and would want to have early breakfast with him. Is this asking too much from an overnight? I'm in NYC. Yankee

[Gar1eth]

Can guys tell me how long an overnight session would be, and what time in the morning am I expected to leave my escort's hotel room by? I've never had sex with a guy, but I did make out with an escort for an hour for the first time earlier this month. Found another escort with great reviews and I want to lose my virginity with him but i'd rather the first time be with a guy I spend the whole night with-- as I'm guessing it will hurt the first time and be a little easier a few hours later--like at 4am. How long does an overnight last? Is it okay for me to expect or ask to get nailed twice during an overnight session? I'd stay in the room the whole time and would want to have early breakfast with him. Is this asking too much from an overnight? I'm in NYC. Yankee

 

No, it's not. I've in the past- I'm not hiring now for financial reasons- scheduled many overnights and weekends. While like you, the 1st time I has sex was with an escort (total virgin- hadn't even Fr. Kissed before). But unlike you, I couldn't imagine wanting to spend an overnight or weekend with a guy. So good for you!!!

 

As to the time, it's all up to you and the escort. I think I've seen as short as 6 hours listed- to 8 or 12- or nebulous end time. Since when I did an overnight -or weekend-while sex was important -companionship was key too. Being a solitary guy, I liked to treat my overnights as dates. So I usually had something planned like going out to dinner and then to a movie or a play. Escorts with strict timing rules for overnights didn't usually work for me.

 

I think one of my last overnights- well it was the end of a weekend actually - ended around 11:30 AM. the escort had gotten up early- around 7 AM to work out at the hotel gym. Came back and showered and did some email. I got up around 9:30-showered- we went to the restaurant in the hotel for breakfast- came back-I packed and left.

 

Gman

[jimboivyo]

rather than get a dozen 'expert' responses here, just communicate with the escort and figure out what works best

[big-n-tall]

As has been stated, you're going to get various answers from this board about what constitutes an overnight and its length of time. As has also been stated... communicate with the escort about what his overnight hours are and what to expect.

 

People do overnights for different reasons. Sometimes sex is involved and sometimes it isn't. Depending on the chemistry and what you have discussed with the escort sex can happen multiple times.

 

Good luck and I hope your "first time" goes well.

[Epigonos]

Jimboivyo and TGuy have given you the best advice possible -- take it, go for it and enjoy the ride.

[loverboy95]

Different escorts have different definitions of what makes an overnight. You'll have to take it up with the escort and see what he says.

[gallahadesquire]

Can guys tell me how long an overnight session would be, and what time in the morning am I expected to leave my escort's hotel room by? I've never had sex with a guy, but I did make out with an escort for an hour for the first time earlier this month. Found another escort with great reviews and I want to lose my virginity with him but i'd rather the first time be with a guy I spend the whole night with-- as I'm guessing it will hurt the first time and be a little easier a few hours later--like at 4am. How long does an overnight last? Is it okay for me to expect or ask to get nailed twice during an overnight session? I'd stay in the room the whole time and would want to have early breakfast with him. Is this asking too much from an overnight? I'm in NYC. Yankee

 

Please, Please, Please see him at least once for an hour or two before your overnight.

I couldn't figure from your post whether this is the same fellow that you've already seen.

Make it even just a dinner, if you don't want to get more involved leading to more intimacy.

 

Going full headstong into a weekend with someone you don't know, especially under your circumstances,

is a recipe (or, in medicine, a prescription) for disaster.

 

I've only once started with a weekend, and that was with someone I'd chatted with for five years on AOL!

[wisconsinguy]

I very much understand your questions. i celebrated my first anniversary recently of hiring. I had excellent recommendations from members of the forum. However, I did digress from recommendations. I hired for a weekend. Friday eve through Sunday sometime. Stayed with the escort, and never looked back.

For that full weekend, three grand. Worth every penny to this date. PM anytime...

[+ purplekow]

I believe he is asking about an overnight. The evening hours may be spent getting you relaxed enough and calm enough to actually engage in sex. The first time will likely be awkward. DO NOT do what i did and get frustrated with the process and just yell out, push the fucking thing in already and then live to regret it when he does. Lube, lube and more lube but your partner should know that and do that. So the evening should be all about getting it in. Then,if that went well,the rest of the time you are together should be getting you off. Whether that is sexually, mentally, spiritually. I hope that you have a great time. If you are up for 2 encounters that is kind of a baseline for me. i like to shoot for 4, and usually shoot in all 4, but I figure, there are just so many orgasms one can cram into one's life but I am going to get every last one I can.

 

But to answer your question: How long is an overnight With the right escort not long enough.

[big-n-tall]

Please, Please, Please see him at least once for an hour or two before your overnight.

I couldn't figure from your post whether this is the same fellow that you've already seen.

Make it even just a dinner, if you don't want to get more involved leading to more intimacy.

 

Going full headstong into a weekend with someone you don't know, especially under your circumstances,

is a recipe (or, in medicine, a prescription) for disaster.

 

I've only once started with a weekend, and that was with someone I'd chatted with for five years on AOL!

 

I do find validity in what you say, especially it being the op's first time and first overnight. I myself try to do at least an hour with someone I've never met as a rule. However, rules are sometimes made to be broken. There are a number of guys I've met where our first meeting was an overnight. All of those meetings went very well, and of those, only one was a well reviewed escort.

 

With that said, the op and his hire might spend a good amount of time getting to know each other before the actual deed is done. They may spend hours just talking depending on what time they meet. This may be better to relax him than just meeting for an hour. That is if he's nervous about the encounter.

[Irtwo]

DO NOT do what i did and get frustrated with the process and just yell out, push the fucking thing in already and then live to regret it when he does.

 

That was hilarious!

[TruHart1]

I very much understand your questions. i celebrated my first anniversary recently of hiring. I had excellent recommendations from members of the forum. However, I did digress from recommendations. I hired for a weekend. Friday eve through Sunday sometime. Stayed with the escort, and never looked back.

For that full weekend, three grand. Worth every penny to this date. PM anytime...

 

Hey WG2. Happy anniversary to you and RGM! Your happy progression in this particular case of weekend hiring was contingent on the escort being who he is, which is why it turned out so successfully for you!

 

Yankee, I am in total agreement with those advising you to talk with your desired escort concerning how long he considers an overnight appointment to be so there is no misunderstanding. Multiple acts of pleasure are certainly allowed during most overnights!

 

I believe he is asking about an overnight...etc.

 

But to answer your question: How long is an overnight With the right escort not long enough.

 

Taking all this into account, I absolutely agree with PK. If you find and hire the right guy, any session spent with him, be it an hour or an overnight, will never seem to last long enough!

 

TruHart1

[american executive]

Hi Yankee

 

You are receiving good advice here. I wanted to wish you the best with you first full experience. have fun

[buckguy]

The try them out for an hour thing is overrated. What you do in an hour is different than what you do for an overnight--some guys, esp. the young and/or inexperienced may not know what to do to fill in an evening, esp. with a newbie, even though they might be okay for a quick roll in the hay. And OP wants an overnight presumably to make some connection, rather than a quick roll.

 

Find an experienced guy who is recommended for newbies and gets good reviews for overnight. A few runs of the search and some looks at guys in your area or where you want to go should be your guide.

[rvwnsd]

As others have stated, the number of hours associated with an overnight vary from escort to escort. The best way to find out is to ask the escort with whom you are interested in spending the night. However, my advice is to stay away from an overnight at this point, particularly if your first date with that escort also happens to be the overnight appointment. You don't know whether you will like him well enough to spend an entire night with him, which could lead to disaster. At the same time, I understand your wanting to ease your way into taking a guy's cock and might want to try it and then rest, try it again and then rest, and so forth. Here's a suggestion: a two- or three-hour appointment. That will give you plenty of time to have some foreplay, let him play with your ass, tease your ass with his cock, take a break, and start the process again and eventually let him slide inside and fuck you. If the evening goes well, you can hire him again and get some additional practice getting fucked.

 

Hope that helps.

[BabyBoomer]

what time in the morning am I expected to leave my escort's hotel room by?

 

Yankee- Who's paying for the hotel room? You or the escort?

 

~ Boomer ~

[Becket]

An overnight is endless when you find out in the first five minutes you and he have nothing in common. If you're bound and determined to do an overnight, at least select someone who is well reviewed and experienced.

[Guest Starbuck]

Yankee, the length of the overnight seems to me to be the least important part of your question. If you'd be staying in the escort's hotel room the whole time (not going to dinner together), I'd guess that your overnight might start at 9 or 10 in the evening rather than, say, 7 or 8, and a later start probably means an early breakfast together is possible. But as others have told you, the timing of your session is going to depend on what you and the escort discuss and agree upon.

 

Your reference to being in the escort's hotel room makes me think you've set your sights on a traveling man. If he's a popular guy, in town for a short stay, your overnight may be bookended by other appointments. All the more reason to discuss the time frame and your expectations ... because I wonder if the mention of sex at 4am means you're planning on an all-nighter as opposed to an overnight? (Realistically, there's likely to be some SLEEPING during an overnight.)

 

Finally, for this first time experience, I hope you've chosen your man thoughtfully. Read "the fine print" in his reviews. Some guys who say he is a great top may love getting pounded. Is that what you want, or are you hoping for something that feels more like lovemaking? If a man is well-reviewed, you should be able to pick up some insights into his style -- whether he's a guy who is attuned to his partners, skilled at getting them ready for his cock, mindful of whether he's giving pleasure or causing pain. Skill levels vary widely.

[+ Topseed]

Communicate, communicate!

 

For one thing, if morning play is on your agenda, ask the escort his attitude towards that. Some guys are not at all interested in a morning romp; best to find these things out ahead of time.

[wklucas]

One of my best overnites - hot guy (of course).....began around 4pm w/a play session (both of us shoot)....out to eat....back to the hotel....his exact words to me - "I'm here to be used & abused"...."nails me twice before we fall asleep (both of us cum both times)....then around 2am - he's sound asleep on his stomach....I crawl on top of him just to rub against his bod.....he wakes up & (the total top guy) is thinking I'm getting ready to nail him....he rolls me over, nails me (we both cum) .....then in the morning, he asks me if I want to do it again.....needless to say, we both cum again.......once again, hot, hot man (San Luis Obispo guy who advertised himself as a former professional baseball player).....all for the grand price of 150 total.....true story - really long time ago (mid 80's)

[jimboivyo]

One of my best overnites - hot guy (of course).....began around 4pm w/a play session (both of us shoot)....out to eat....back to the hotel....his exact words to me - "I'm here to be used & abused"...."nails me twice before we fall asleep (both of us cum both times)....then around 2am - he's sound asleep on his stomach....I crawl on top of him just to rub against his bod.....he wakes up & (the total top guy) is thinking I'm getting ready to nail him....he rolls me over, nails me (we both cum) .....then in the morning, he asks me if I want to do it again.....needless to say, we both cum again.......once again, hot, hot man (San Luis Obispo guy who advertised himself as a former professional baseball player).....all for the grand price of 150 total.....true story - really long time ago (mid 80's)

 

 

cool story bro

 

times have changed

[loverboy95]

One of my best overnites - hot guy (of course).....began around 4pm w/a play session (both of us shoot)....out to eat....back to the hotel....his exact words to me - "I'm here to be used & abused"...."nails me twice before we fall asleep (both of us cum both times)....then around 2am - he's sound asleep on his stomach....I crawl on top of him just to rub against his bod.....he wakes up & (the total top guy) is thinking I'm getting ready to nail him....he rolls me over, nails me (we both cum) .....then in the morning, he asks me if I want to do it again.....needless to say, we both cum again.......once again, hot, hot man (San Luis Obispo guy who advertised himself as a former professional baseball player).....all for the grand price of 150 total.....true story - really long time ago (mid 80's)

 

Sounds hot!

[Traveler North]

"Overnight" length depends on guy. Most, in my experience, do roughly dinner to breakfast. Yet recently, met one for overnight who was willing to do early afternoon to 9am. Beware, some will only cum once a day and, as said earlier, some do not do morning "awakeners." Luckily most my guys enjoy romps any time.

[adriano46]

I used to hire mostly for overnights (in Europe, where prices were more reasonable) but usually also after meeting the guy for a few 1- or 2-hour sessions to see how sexually compatible we were. For most of these, the date started in the very early evening, drinks, a nice leisurely dinner or dinner and the theater, then back to the hotel for the "first" session that I always preferred take place in the shower... then a glass of wine and chat and a more sensuous but sweaty session before falling asleep.

 

I am a very early riser and know that 95% of the guys I hired for overnights are definitely NOT. I always discussed the morning sex question before we even began the date (primarily as I am most horny in the morning with my coffee... go figure?) It would be a complete let down to engage a guy for an overnight who barely can function until 10 am (and I have, and no, it is not at the least bit enjoyable trying to have sex with a guy asleep (or feigning sleep). As in most other aspects of hiring, COMMUNICATE with the escort your expectations (and understand his boundaries, limits, or whatever).

[samandtham]

I've only hired a guy overnight once; my opinion on the matter may not be as good as someone who has had a few under their belts. (Pun not intended, I guess?)

 

The guy was actually a rehire; did a two-hour session with him several months beforehand. We met up at 7PM at my hotel room, did a quickie, showered together, and went out for dinner and drinks. I'm comfortable with him, so the hours went by like nothing—our conversations were always lively and spirited.

 

We came home around 1AM, and went for round two.

 

The next day, he woke up the same time as I did, which was close to 9AM. He asked if I wanted "breakfast" in bed, I agreed, although I told him that there's a possibility that I won't do well. (Sorry, I choose sleep over sex any day ) I didn't finish although he did. We both got dressed, I offered proper breakfast, but I said that our time is already over. He didn't mind. We parted ways at 11AM.

 

The TL;DR version:

1. If you can, hire him for a two- or three-hour session before you commit to an overnight.

2. Be upfront about your expectations—frequency, roles (I prefer versatile guys for this purpose), what you'd be doing when not lovemaking, and the morning after. Everyone rolls differently, moreso if you're hiring him for momentuous occasions (like popping your cherry), so divulging that at the start is helpful.

3. Allow about 6-7 hours of sleeping time.

4. Always treat the guy with respect.