Virgins/inexperienced guys

[1373263]

How do you feel about getting involved with guys who are new to M2M sex or have a limited amount of experience?
Some friends and I were discussing this the other day and a couple expressed a dislike of sex with inexperienced guys, and said they would decline to get involved with virgins for a number of reasons. This discussion arose as I have been "assisting" a shy and closeted man who is/was new to M2M sex over a period of time recently...

Comments please?

 

[halcyondays]

Over a period of time is right!

I've introduced a number of guys to MM sex over the years. Preparation and practice in advance of anal penetration takes the most time. Multiple sessions are required.

I've even provided enema kits, butt plugs & lube/Injector as homework assignments to let guys get used to it in their own time. Some learn it's not for them. I was forty before I started to bottom so you never know how your body might change over time.

For those who just want to develop/hone sucking skills? Get busy. Daddy can handle it.

 

[WilliamG]

Hmm... I'm one of those guys.

Is it out of concern for the act of anal as @halcyondays said? Or just the whole sexual process? Perhaps in the same way an experienced straight guy passes on a female virgin not wanting to deal with "the learning curve". Or just the initial awkwardness of being new to it?

That said, many of us bicurious guys have a LOT of anal toy experience under our belts. Just not the real thing.

 

[dickthrobbing]

We all had to start somewhere. The first guy I hooked up with was a great coach took his time and I had a great experience. I like to thing I do the same for new guys I've bedded

 

[Assman1]

Help! I'm one of those men.

 

[goldscorpguy]

Quite a few of my hook ups over the years have been with guys at just the curious stage. I've always enjoyed being their first real experience and see it as quite a responsibility. I try to be calm and understanding, and go at their pace not mine. It also adds an extra dimension to my excitement knowing that I am their first time.

 

[1373263]

Quite a few of my hook ups over the years have been with guys at just the curious stage. I've always enjoyed being their first real experience and see it as quite a responsibility. I try to be calm and understanding, and go at their pace not mine. It also adds an extra dimension to my excitement knowing that I am their first time.

Yes, I've been there before and really appreciated the calm understanding and patience.
The situation with the guy I have been assisting is something like this; I have also posted it here in case it is thought that I'm not gay enough when I'm interested in men or something...
I met him when I was working on the windows of his house over the summer. He was working from home at the time, is single, mid thirties, owns his own house and came across as straight. I soon noticed he would come for a chat and talk to me for an hour or more, and offer me a coffee about 5 x a day- nothing unusual there for some people. After about a week working at his house, I picked up that he was checking me out while talking to me and other times during the day, but continued to otherwise act straight. I started quietly checking him out from time to time, and wondered if I was wrong about the straight part as I increasingly noted him checking me out in an awkward manner. I decided to test him by wearing short shorts with boxers underneath and I soon had my answer- it was so obvious that he liked what he saw, but he noticeably kept away during the day. I continued to wear the short shorts over the next week and soon realised that not only was he was unable to keep his eyes off my shorts, but he knew he was attracted to me and was uncomfortable about the fact.
He made a cuppa on thursday afternoon of that week and while we were sitting talking, he was unable to stop staring at the front of my shorts- I was soft but filling the shorts out and it would have been even more obvious with boxers on too. I very quietly and neutrally asked him if he liked what he saw; his response was total panic and then denial. He eventually nodded without looking at my face and I quietly mentioned that I had noticed his interest and that I was OK with it. He looked at me ashamedly and I reiterated that I was OK with his attraction toward me. He seemed surprised that I had worked out his interest, had broached the topic and mentioned I was OK with his interest.
I left him to it that evening at 6pm, but when I was packing up to leave he was again staring at me as i bent over and packed my cases, and this time without trying to hide his interest. Immediately before I left, I took his hand and brushed it across the front of my shorts before telling him I would see him again tomorrow at 7am. He was shocked by my action but didn't object or pull away.

 

[1373263]

That said, many of us bicurious guys have a LOT of anal toy experience under our belts. Just not the real thing.

Isn't that the truth! I was so used to my dildo that taking a cock was no issue whatsoever when it happened, it wasn't until a bit later that I found pleasure in butt stuff.

 

[WilliamG]

Isn't that the truth! I was so used to my dildo that taking a cock was no issue whatsoever when it happened, it wasn't until a bit later that I found pleasure in butt stuff.

I don't want to brag... But a 1.9" dia x 9" long is not out of the question for me. I don't expect to find to many guys in that range. The truth of it may be that a big guy who doesn't ease his way in may be a LOT different than the way I do it.

 

[1373263]

I don't want to brag... But a 1.9" dia x 9" long is not out of the question for me. I don't expect to find to many guys in that range. The truth of it may be that a big guy who doesn't ease his way in may be a LOT different than the way I do it.

Yes I can understand that one- I have a favourite dildo about 1.5" dia at the head which I can take without issue, but it does require some relaxing and work to insert-that's half the fun IME. For a newbie with a partner who is not patient and/or on the large side I could see a significant issue, but I don't think about inexperienced guys like that at all (hence my question).

 

[1373263]

Friday morning I arrived at 7am and he offered me a cuppa straight away, which he made while I shifted my cases from the van. We sat down at the kitchen table and there was awkward silence from him while I discussed the work I would do that day. It was clear to me that what I needed to do on his windows that day was the last thing on his mind- he was staring at the front of my shorts again. I decided that I would let him stew all day and didn't say or do anything to either escalate things or distract him from his interest.
I thanked him for the coffee and got on with my work, again he was checking me out while I worked and I tried hard to concentrate on my work. He managed to work through until about 3pm when he offered me another cuppa. While he was making the coffee I noticed he touched himself a couple of times, adjusting like he was uncomfortable with his bodily response. I pretended I hadn't seen anything, but it got me thinking about what sort of effect I'd had on him with my short shorts and brushing his hand across my shorts the day before, and I started to harden too. If he liked me in that way and it seemed he did from his staring, it was no wonder he was responding and if he were uncomfortable with his interest then his physical response and mine would be even more embarrassing to him. I decided to play it cool and made small talk about his work and what I had achieved during the day; when I had finished my coffee I excused myself and went back to work. As I worked I considered the fact that he was clearly attracted to me and likely knew it was mutual, but was also uncomfortable about his attraction. I considered the fact that he had only responded physically (as far as I knew) since I had asked him if he liked what he saw and teased him a little; my conclusion was that he was either really shy or totally inexperienced with men.
At 5 pm I started to pack up my tools and noticed him staring at me as packed things up; I realised that he was openly showing more interest and decided while I worked that I needed to either make a move or stop teasing him. I packed the van and went back inside to show him what I had achieved during the day; while I was showing him my work I noticed him becoming harder and adjusting himself; after we had finished discussing his windows I told him that I had noticed his interest and physical response to me over the previous week, and asked him if he wanted to know more about his interest.
There was a short silence and he wouldn't look at me, but he did eventually reply with a quiet "yes, I need to". I responded by putting his hand on the front of my shorts so he could feel my growing cock; I held it there for a couple of minutes while we looked at each other and he eventually met my eyes. I could see him hardening too and I put my hand on his growing mound for a minute, before quietly pulling back. I told him that I needed to go but would be back on Monday at 7am and he nodded and agreed.
On my way home in the Friday traffic I received a text message from him, could I return tomorrow, there was a window he couldn't operate properly...

 

[1373263]

Saturday morning arrived too slowly for me; I didn't sleep well thinking about what had happened on Friday and the "issue" with the window. I almost never have callbacks because I check everything thoroughly before handover, so I was fairly sure it was a premise. In any case, customer service was important to me and so I headed to his place to investigate the matter.
When I arrived he greeted me at the door before inviting me inside; he was wearing boxers and a tee shirt- I tried not to look down at his shorts but there was something making me want to look... I liked the sexual tension building with this guy and where it was leading.
I asked about the window that was giving him trouble and he indicated one that I was sure was OK - I was sure I knew why I had been called back now but checked the window in any case, Checking the operation of the window took maybe 10 seconds; there was no issue with the window as expected and I advised him it was working correctly, and asked if he could show me how it was giving trouble. As he moved past me I could smell his slight musky smell and also became aware that he was tenting the front of his boxer shorts; I responded in the same way as he operated the window and found it did open and close without issue. We moved into the kitchen and sat in the kitchen. As we talked I took his hand and placed it on my hardening cock while looking straight at him; I knew why he had called me back and he now knew that I knew. He couldn't maintain eye contact for maybe 15 seconds, then looked back up at me and held my gaze. I removed my hand and he left his hand in place on my cock; I told him it felt good before tentatively placing my hand on his cock. He pressed my hand toward his body and we both both closed our hands at the same time, each other's cock in our hands.
We both stood up together and I could hear my pulse pounding in my ears and could feel his pulse twitching his cock; we held each other for a couple of minutes before I tentatively touched his bum. My touch became firmer and I could see from his reaction he was both excited and apprehensive about the new touch, he slowly relaxed.
I gently moved both hands onto his bum before drawing him in closer so we were touching at the hips. He responded by putting his hands on my bum and our cocks were pressed together; we were both very hard and I could feel myself starting to dribble in my shorts. I quietly asked him if he had ever done anything with a man before and he replied "no"; I continued by gently asking him if he wanted to and there was silence before he replied "yes, I do". I asked him if he was sure and didn't receive a response for a couple of minutes, before he told me he liked it so far and wanted to continue. I asked him specifically what he liked and he wouldn't reply, but pulled me in tighter.
I massaged his bum cheeks while I was holding him and he responded by touching my balls; I was definitely dribbling now. I gently kissed the side of his neck and he quickly responded by holding onto me; his pulse quickened and he eventually started kissing me, tentatively and then more confidently as I responded to his attention. I took my hands off his bum and placed them onto his chest; I rubbed his nipples, gently at first and becoming harder as I felt them stiffen. Between kisses I asked him if he liked to have his nipples touched, and he replied with a quiet "yes, I like it"; This was the most definite verbal response I had received so far - I was making sure he liked what was happening before going further, so he felt in control.
We were both still clothed at this point and my shorts were developing a serious wet spot. I moved one hand off his chest onto his boxer shorts and started to remove them; when they dropped to the floor he stepped out of them. His cock was fully hard, a little smaller than mine and uncut. His balls were larger than mine and hung low and I gently fondled them while continuing to massage his nipples with my other hand. His cock twitched every time I rolled his nipples between my finger and thumb. He undid the drawstring on my shorts and dropped them along with my boxer shorts; as my cock sprang free it drew out a string of precum which snapped and dripped from my cock. He noticed and immediately touched the precum on my cock, slipping it between his fingers before looking at me. "Precum" I explained; He obviously hadn't seen it before as he was obviously fascinated by the sticky stringy fluid and even more so when he noticed the sticky wet patch in my shorts.
I drew him in close and started kissing him again while touching his balls and taint; I couldn't believe how low his balls hung and his scrotum fascinated me. He responded by spreading his legs apart, making it easier for me. I gently massaged his taint and moved toward his anus; he responded by spreading his legs even further and whispering "please". I massaged him as much as I could from a standing position; he soon understood the limitation of his stance, and moved my hand to touch him from behind. I massaged his arsehole and taint for at least 10 minutes before I asked him if he liked that. "Yes, he replied "keep doing that". I kept going and started to gently finger his anus; he responded by telling me to use the olive oil!. I found the can on the bench and lubricated my finger with the oil before continuing; he responded well to the touch and soon relaxed enough to fit a couple of fingers. I was surprised at how well he responded to arse play and his suggestion of olive oil.
He sat on the kitchen table and lifted his legs in the air and I instantly realised that he had played with his arsehole previously and had little other experience- he was used to touching himself there and knew the ways to do so, whereas his responses to touching and kissing indicated apprehension.
I slowly inserted my forefinger into his anus and gently rubbed the top wall of his passage. His cock twitched as I did so and I concentrated my touch on areas that kept his cock twitching. He moaned as I did so and after about two minutes, came in several powerful spurts on his chest.
I was literally making a puddle by this time and he eventually noticed; he very tentatively touched my cock head and slipped his fingers about in the precum for a minute until I came into his hand with three shots of very thick sticky cum.
We cleaned up in the bathroom and he showered; not much was said by either of us but when I mentioned Monday he quietly agreed.

Sunday morning I had a text message from him, could I visit today. I replied that he should rest and I'd see him on Monday.

 

[marriedguybutcurious]

Want to experience man to man stuff/s in real life.. never been with a guy..

 

[curtdude]

I have had some virgin dudes to MM sex. One told me that they had never done anything with a guy before. I did not force them into anything the did not want to do. James and I were just hanging out he brought up my sexuality I told him that I was into both. He mentioned he was curious and would like to explore it with me. We went very slow ended in the bedroom I pulled off his shirt and shorts we both in our boxers on the bed those came off I worked me way down and gave him a bj I slowly fingered his hole. I kept a eye on his reactions to what I was doing to him moans and sounds of goodness. Sucking on his cock and balls doing the things I liked done to me. As I slowly inserted my finger into his hole looking for that prostate there was a little resistance from him I told him just go with it I could feel him relax and I massaged his prostate as i sucked he started to react to what I was doing oozing precum by y the gallons. I played with his nipples too I could tell he was getting close so I stopped and let him calm down a bit as I grabbed the lube. I asked him how he was doing and with a big smile nodded yes. I lubed up and told him that we could stop if he wanted I got on top of him and we made out for a while and I looked I’m in the eyes and lifted his legs I nodded yes he replied yes back I slowly put my cock on his hole and nudged it in slowly . He felt the pressure of my head pushing in as he looked up at me. I my head popped inside him and I just stayed still untill he got used to me. I slowly pushed in until my balls were on his ass. I started to pump his ass us was moaning very loudly his cock was in between us rubbing between our bodies I felt his grip on my cock tighten from his hole he was having a orgasm and spewing his load in between us that pushed me over I pushed in balls deep and I unloaded my sperm inside his ass. We layed there in a heap of sweat and exhaustion. I moved down and licked up his goo from his stomach then kissed him. I think for his first time with a guy it was a great experience.

 

[1373263]

As I sat in the van outside his house on Monday morning, I hardened as I thought about what had gone on the previous week. Here was a guy who was shyly attracted to me, slowly exploring his interest in men; it clearly wasn't a new interest but equally so, he wasn't comfortable with it although I had seen signs that he was starting to become more comfortable exploring his interest with me. In some way, I was excited that I was mentoring a curious man but also determined that his experience with me needed to be a good one and led by him, at his pace.
As I carried my tool cases into the house, I could feel my tool belt rubbing against my erect cock and realised that it would be very obvious to anyone; the feeling made me harder still as I knocked on the door because I knew he would notice immediately.
He opened the door and ushered me inside; he was wearing a tee shirt and a towel. I put my tool cases down in the room I was working in and turned to go out of the room. He was standing in the doorway and I saw his eyes drop to look at my cock as I took off my tool belt; the towel didn't hide much and as I approached him, I put one hand on his hard cock and the other on his chest. He immediately responded by drawing me closer and tentatively placing his hand on the front of my shorts. I took my hand off his chest and used it to move his hand into my shorts; I felt his cock twitch in response to my touch and time seemed to stand still as we explored each other, his touch was tentative at first and became more confident as he explored. His towel was soon on the ground followed by my shorts and boxers, and our tee shirts soon after; he was becoming more confident in his exploration and I was happy to be explored at his pace. He had obviously recently showered; I knelt in front of him and touched the tip of his cock with my tongue; his cock immediately twitched and he gasped; I continued to touch his cock head with my tongue before sucking his whole cockhead through my part-closed lips. He moaned softly and I repeated the action again and again until he gently pushed me away; he was getting close and wasn't sure what to do. I responded by sucking his cock through part-closed lips, much more slowly until I felt his cum spurt into my mouth. I swallowed the salty load and kept gently swirling my tongue over his cockhead until he eventually pulled away. I stood up and drew him in close, massaging his arse cheeks. He responded by kissing my neck and slightly spreading his legs, and I slowly moved my attention inward to his taint and hole as we kissed. I touched his hole gently and then more firmly and I massaged his hole with my fingers until he eventually relaxed. I explored for a minute with one finger, and then two before he stopped kissing me; he led me into the kitchen and sat on the kitchen bench, legs in the air. I continued to massage his hole for a minute and then pulled up a chair. I sat down in front of his arse and started to gently tongue his hole, in small strokes to start with and increasing until I was touching close to his taint. His moans became louder as I gently pleasured his hole; his legs trembled and cock twitched. I continued my attentions, becoming firmer and more vigorous as his moans became louder; I concentrated my efforts on his centre, slightly spreading his hole with every thrust of my tongue. His hole relaxed and I continued my tonguing efforts while gently touching his soft pink hole with my finger. He moaned and squirmed, moving his lower body forward to receive attention. When I noticed his scrotum tightening, I quickened and concentrated my tongue action until he came up his chest, a smaller load this time. I slowly removed my tongue from his twitching hole but he pulled me back toward him until the orgasm had subsided.
When he had recovered somewhat, I led him to the shower and we continued to touch while showering, relaxing and winding down. I gently asked him if he had enjoyed the MM sex during the morning and he turned red with embarrassment. When I prompted him to tell me which part he liked the most he was silent for a minute but the expression on his face told me that he knew what part he liked; eventually he told me that the blowjob was like nothing he had ever experienced and helped him continue, despite his apprehension. I asked him if it was his first time with a man and he quietly admitted that it was; I asked him if he wanted to explore MM sex further and his response was a quite but definite "yes".
I continued with my work that afternoon, working inside in my boxers and a tee shirt; he regularly came to where I was working and we kissed and fondled for a minute or two before going back to our tasks; he was always hard when he came to me and we were both hard when he left. My boxer shorts had a big wet mark on the front and strings of precum stretched and broke every time he withdrew his hand from my shorts; by the end of the day they were quite wet and I removed them before putting on my shorts to go home. I don't think either of us achieved very much in terms of work that day but it was well worth it.
I was hard the entire drive home, thinking about him and his reaction to my attention, and the fact that he had never experienced MM sex before. I couldn't get past the fact that he was definitely interested in further exploration, and that he had come to me and started touching me at least 5 times that afternoon- quite different to the shy guy who couldn't admit to himself that he was interested in men.
I didn't sleep much that night, thinking about the day's events...

 

[krazioso13]

Just my two cents here..maybe three cents. For my own path and what I've done, and what I will continue to do, it's a gamble for me. Maybe for others if they just don't realize it at first.

First cent is, I like it a lot..i really do. of course, I have no expectations on a good BJ, or getting any kind of recip. For me, its a massive plus as they groan/moan a lot, cum fast(love that), and those legs shake/tremble when licking, nibbling, feeling and tasting them up. Another major plus is, their buttholes are extra tight and just a slit, and its so good eating them out and showing them how good anal can be when going slow. The way they open up and more is just damn good fun. Last thing is, some surprise when by trying to bttm or suck me since I have a smaller cock.

Second is, the gamble that the guy could end up very clingy or "bonding" deep over the fun. Now, that isn't only for younger guys who are inexperienced and/or curious. I've had guys in their 20's and 30's, hell, even 40's, be the same way. That they receive slow/good sex and they think they caught feelings or after a few meetups, they think they are "in love". That's always been a rough situation to break, yet, i realized, there almost is no legit reason to address it negatively. Just talking upfront, stern and with conviction/thought helps a lot.

My third cent is..if I ever find or get with a guy and he's very sexually inexperienced and I legit want to be with him, i will attempt to focus on the positives. Meaning, sure, he doesn't know what's up or what he's doing, yet, that can't outweight the fact that I can make it fun and make it a damn good memory that gets us rock hard when we think of it time later, or make newer versions of it. That might solidify our bond deeper and higher trust too.

So yea..just my few cents

 

[MNpervert]

I dont mind topping a virgin but I do not like bottoming for one.

 

[ChubbyguyDK]

Well i Would surely hope that someone out there are willing to take us inexperienced under their wings. I for my case is a 40 year Old Virgin due to insecurity/aspergers and lack of opportunities where i live. So the experience I have is through tube and Tumblr and my right hand.