Note: If I interest you and you want me to be interested in you, then when you send me a note, remember that if it's a 'nothing note', I won't be responding. I took time to write a description that I hope will attract men I could be interested in. If your note to me is not interesting, why do you imagine you'll interest me?
I am a real dad, and understand and appreciate the guidance and mentoring the role calls for. I also long for a sexual component to that role - absent, of course, with my children - and I enjoy the attraction that young men, especially skinny ones, have always held for me.
I'm a top by temperament, and understand the rights - and responsibilities - of the position. That said, I am not averse to exploring my bottom side with the right man. My geographic location dictates that most of my interaction on this site will be virtual, but I like to think that I have a good [and dirty] enough imagination to provide an enjoyable experience for a boy who is able to participate in weaving the web of cyber-sex.
Because I am a dad, and thoroughly enjoy the teaching/mentoring aspects of that position, I've written a 'first time' guide for new bottoms in an attempt to make the experience as enjoyable and safe as possible. I've included it below. Bottoms can use it as a guide, and tops can see some of the things that they might pay attention to. I look forward to developing relationships across the generations.
I recently received the following note from a man in his mid-70s: 'Actually right-on with your guide! A close friend and I had anal sex for a very long time when we were both late teens/early 20's. We experienced everything you speak of and you are right on target. I have used the same technique [especially the 'spoon-fashion' position and the bottom backing onto the cock] in the following years and have enjoyed so much giving and receiving. '
First Time Guide:
General considerations: It is a good idea to have various pieces of 'equipment' readily to hand so that they can be accessed if/when needed without interrupting the 'proceedings'. That equipment should include lube, condoms, a hand-towel or some hankies [to wipe lube off fingers and mop-up cum], and a firm pillow [6 inches/15cm high] with a easily-washed cover to help with body-positioning, angle-adjustment.
Your partner should be a 'good and experienced' top - and by 'good' I mean that he should be closely attuned to you. One of the responsibilities of a good top is being able to 'read' his bottom, and adjust his actions to enhance the pleasure of the bottom. He should be aware that it is your first time - although you may have experimented with various objects, it's different when there is another person [and anxiety] involved. After mutual disrobing [even though it's more difficult, having him remove your clothes, and having you remove his is both more erotic, it also helps to develop trust and co-operation], you should explore each others' bodies with your hands and mouths. As your excitement level increases, direct genital touching and JO will heat things up nicely.
As you get ready for penetration, he should dilate you gradually by using his fingers [well lubed, of course], first one, then two, then three. With each additional finger, there will be more stretching for you. You should be sure to let him know how you're doing. After each increasing stretch, you should 'clamp down' on the inserted finger[s]. That action, repeated, helps your sphincter to become accustomed to the stretch. He should reach far enough inside you to gently rub [not poke] your prostate. That should be very pleasurable for you. He should also gently hold and stimulate your cock and balls, thus associating the pleasurable feelings from both ends. If you feel yourself get close to cumming, let him know so he can back off - if he's a good top, he should already know.
For the big event, I suggest that you lie on your side with your knees bent up so that your legs are about in the same position, relative to your torso, as when you're sitting in a chair. That will make you 'accessible' but not cramped up. He should lie behind you, with his chest against your back. His lower arm can reach under you to hold your chest close to him - perhaps stimulating your nipples if you like that - while his upper hand should gently hold your cock and/or balls. This position is preferred because it allows both partners to relax, without using any energy to maintain position. It takes gravity out of the equation. The first penetration can take a long time. It also allows the bottom a clear route of 'escape' if the discomfort becomes too intense. As the penetration is proceeding, the top will feel a strong urge to thrust forward - it's instinctive. A good top will be able to resist this urge, let your bottom set the pace for his first time. The actual positioning of the top's cock-head is something that you, the bottom, should do - you know where the target is, and can also make sure that the condom is in place. For the penetration itself, the top should lie motionless, letting you back up onto him at your own speed. It's a good idea to be sure that he's entering you straight-on [because cocks come in a variety of angles, move around so his cock is aiming straight for the hole]. If the cock enters at an angle, it can poke at the sphincter muscle-ring he's trying to penetrate - that HURTS, even for experienced bottoms. It helps, as he's going in, if you 'bear down' [like you're trying to take a shit]. Your body associates that action with opening the sphincter. You should slide him in at a speed that works for you. You probably will want to adjust the tilt of your pelvis to his angle. Once the head is in, you can exercise your clamping muscles to help accommodate your body to him. Alternate 'bearing down' and [further penetration] with clamping down on the additional inserted length until he's fully in. Don't try clamping down as he's moving deeper - that's likely to hurt. Depending on how big he is, and how you're constructed inside, there might be a cramping sensation as more of him is inside of you. If that happens, just back off a bit [two steps forward, one step back is a good technique].
This first penetration should not be rushed - it takes awhile for your body to adjust - and after he's fully inside of you, you should lie quietly for awhile - just get used to the sensation of having him inside you while he gently stimulates your cock and balls. When you're ready, you can start to move on him as it feels good to you. He can also start to move inside of you, but be sure to let him know if he needs to cool it a bit. As you become more used to the sensations, you can pick up the pace. You may also want to try other positions [see a discussion of other positions later]. Perhaps you can move into other positions while keeping him inside, otherwise he'll have to penetrate you again. As he withdraws, your sphincter is likely to clamp shut, and that might be painful - just be prepared - and have him withdraw slowly. As he enters you again, it is likely to be uncomfortable again [especially if you're on your back]. Just take it slowly. For me, my favorite position is classic 'missionary' [bottom on his back, legs up, with the top between his legs]. This allows the deepest penetration, and for the partners to stare into each-others' eyes, but it's not recommended for your first-time - the bottom has no escape, getting the angle right can be difficult, and gravity is a factor for both.
If you want to cum while he's inside you, be aware that your sphincter clamps in time with the pulsations of your orgasm. Doing that with a cock inside will feel odd - and may hurt - just be prepared. There are actually two sphincters for the anus, the one at the outside you already know about, and another one about an inch or so inside. With some men, the opening of the two is not a one-step procedure, and there will be a secondary pause waiting for the interior one to open. There is also the difference in cock-design to be aware of. With some men, the head of his cock is larger than the shaft, with others, the shaft is the widest point. As penetration is occurring, that difference will affect the way it feels. It will also affect things during active thrusting: If a man with a larger head withdraws almost completely, the head will sort-of act as a 'retainer' - holding him inside and pulling a bit - before he pops out. Some cocks are also curved - up, down, or sideways. That curvature [if present] may make some positions more comfortable/pleasurable than others. I would anticipate [not having had any actual experience] that having his cock curving towards your belly would be best.
During the first penetration, if the top has prepared you well, you'll be wanting to have him inside you, and once the head has penetrated you - so no more anal stretching is involved - you may be tempted to shove back to take the rest of him. This is a good time to practice restraint. The rectum has a sharp bend quite a ways in, five or six inches [13 - 15 cm], and, depending on his size, having him all the way in may feel uncomfortable - like a sharp cramp. It is a good idea to aproach this possibility with care - take it slowly and let him know if it hurts at deep penetration. If you phrase it in a way that compliments him: ' . . . OH, you're so big it hurts me when you go in so far . . .' he should be fine with exercising a bit of restraint, and your innards may re-arrange over time to accommodate more/all of him as he continues to thrust inside you.
Then there's the uncut cock to consider. There is a great deal of difference in the length and tightness of foreskins. If he has a short foreskin that retracts easily, you just need to be aware that an uncut cock is still more fragile that a cut one - more sensitive to abrasion because the skin of the head is thinner, having been protected from rubbing on clothing by the foreskin. If the foreskin is long and tight, it may not retract at all and you won't even be able to see the head except for a glimpse. The man can provide specific instruction about the way he likes to be touched . . . You may also be concerned about cleanliness 'in there'. It would be a good idea to eat a diet high in fiber [oatmeal, dates, apples, bran, fruit (with peel), etc.] to firm-up your 'stool' for a day or two before-hand. You can 'douche' if you want [an enema], but do not use anything except plain water, and no hoses connected to a pressurized water-supply - that can easily do serious damage to your innards including burst intestines. Most of the time - even without douching - there will be no 'besmirching', and a good top should be equipped to deal with any that does occur. It's most likely to happen if your 'stools are loose' [aka 'the runs']. You should not try bottoming if you are constipated - there won't be room - and trying is likely to be very uncomfortable.
When the top is fingering you, he may detect the presence of some 'stool' inside you. If he does, he should gently inform you, and have you go to the bathroom to see if you can eliminate it. There is no shame involved, and it does interrupt the 'flow of the action', but having more room inside will help both parties. Any lube that had been applied will, of course, be removed so it's best to start the finger-dilation again. The action of having the bowel- movement to remove the stool will also likely disrupt the dilation training, so starting again is a good idea.
Having a man inside you presents many different sensations: There is the stretch of having your ass open, there is the friction of having his cock rub against the skin of the opening. There is the sensation of the bulk of his cock inside you, there is the rubbing of his cock against your prostate. There is the sensation of his body moving against your cock and balls [depending on position]. There can also be the sensation of his cock 'hitting bottom' when he goes in deep, and his balls against you when he does. There are also the sensations of whatever he may be doing to other parts of your body with his hands and/or mouth. You can also use your hands to touch him - holding his balls while they swing against you, touching his belly as it flexes with his thrusts into you, stroking his pecks/nips. Talk to each other - find out what feels good . . .
Now a brief discussion of the various positions: Spoon [ back-to-front] position with both partners on their sides is suggested for the first- time. No-one is using muscles to hold position against gravity, and the bottom will be able to 'get away' if the discomfort is too intense. Variants include having the bottom straighten one leg, or lift one. Each of those can change the sensations for both partners.
Cowboy, where the top lies flat on his back and the bottom 'mounts' him [facing in either direction] allows the bottom to set the speed of penetration, but gravity will be working towards deeper penetration. It does have the advantage of very easy angle-adjustment for the bottom, and if he's facing his partner, the opportunity to see each others' faces can add to the enjoyment. It also allows the top unrestricted [and in my case, irresistible] opportunity to play with the bottom's cock and balls. Face-to-face cowboy also allows relatively easy transition to 'missionary' while staying connected.
Doggy, with the bottom kneeling and either hands, elbows, or chest on the bed and the top kneeling behind him allows the top to see where the opening is, and watch his cock disappear. It's relatively easy for the bottom to 'escape' if necessary, but there needs to be attention paid to angle of entry. Depending on the relative upper-leg lengths of the partners, things might not line-up well. One or the other partner can adjust things by spreading knees, or the bottom can move his torso back a bit while not moving the knees. Variants include having both men with their torsos vertical [and touching] or bent-over [also touching]. Each of these adjustments will affect the cock-angle inside and may be more or less pleasurable for each.
Missionary allows the partners to see each other, and the top can have a fine view of his partner. It also allows very deep penetration. The angle can be tricky for penetration, depending on how sharply the bottom is bent at the waist. Here again, the relative heights of cock and target can make a tremendous difference in 'comfort level'. The bottom can have his legs on the top's shoulders, his feet by his [own] ears, his legs around the top's waist, or something else. A variant that allows the bottom some control over penetration is to have the top on his knees, 'sitting' between [or on] his own feet. The bottom can drape his legs over the top's legs, and slowly slide into the top's lap - and onto his cock. A firm pillow under the bottom's butt can help with alignment.
Board, with the bottom lying flat on his belly and the top lying flat on top of him, allows the bottom to hump the mattress and allows great total-body contact. Either partner can have his legs between the other's [it does change the sensations for both].
Scissors, with the bottom lying on his side, either with both legs up like for 'spoon' and the top kneeling behind him with legs spread; or the bottom with the bottom leg straight, the top leg bent, and the top straddling the bottom leg.
Chair, is much like Cowboy except that the top is seated. This will change the thrust-angles and provide for close upper-body contact regardless of which way the bottom is facing. If the partners are facing each other, the top's belly and chest will be close for good contact with the bottom's cock and balls. If the top is strong and/or the bottom is light, the top can stand and carry the bottom around while impaled.
Vase, where the bottom's torso is vertical, head down, with his weight on the back of his neck. The bottoms cock will be pointing directly at his own mouth. The ass will be up, open like a vase, and the top can move his cock straight down and in. I've seen this done with the top taking a number of different positions - including straddling the bottom, one leg in front, one behind. Most of these positions can also be used with one or both partners with one or both of his feet on the floor - each change in leg-placement will bring slightly different sensations to both partners. There are also many others that the more adventurous and/or limber can try. The list above is hardly exhaustive of the possibilities that two horny men can devise. Try different things because the sensations can be completely different. For me, one man having his cock inside another is the sexiest thing I can think of. Good luck in finding a person and position[s] that bring both of you pleasure.
I hope that this guide has been helpful - and has perhaps turned you on reading it as it did me writing it. Please drop me a note if you have any questions/concerns - a good dad wants to take care of his boys.